id string | question string | answer string | documents list |
|---|---|---|---|
1,3-Dipolar_cycloaddition_4048056 | Explain what '1,3-Dipolar cycloaddition' covers in the 'Synthesis of carbonyl ylides from hydroxypyrones by proton transfer' section. | Carbonyl ylides can be synthesized by acid catalysis of hydroxy-3-pyrones in the absence of a metal catalyst. An initial tautomerization occurs, followed by elimination of the leaving group to aromatize the pyrone ring and to generate the carbonyl ylide. A cycloaddition reaction with a dipolarophile lastly forms the ox... | [
"1,3-Dipolar cycloaddition — Reactivity\n\nConjugation, especially with aromatic groups, increases the rate of reaction by stabilization of the transition state. During the transition, the two sigma bonds are being formed at different rates, which may generate partial charges in the transition state that can be sta... |
1,3-Dipolar_cycloaddition_4048049 | Describe the 'Electronic/stereoelectronic effect' section of the article about '1,3-Dipolar cycloaddition'. | The dominant electronic interaction is the combination between the largest HOMO and the largest LUMO. Therefore, regioselectivity is governed by the atoms that bear the largest orbital HOMO and LUMO coefficients. For example, consider the cycloaddition of diazomethane to three dipolarophiles: methyl acrylate, styrene o... | [
"1,3-Dipolar cycloaddition — Reactivity\n\nConjugation, especially with aromatic groups, increases the rate of reaction by stabilization of the transition state. During the transition, the two sigma bonds are being formed at different rates, which may generate partial charges in the transition state that can be sta... |
1,3-Dipolar_cycloaddition_4048033 | Reconstruct the content about '1,3-Dipole' from the article on '1,3-Dipolar cycloaddition'. | A 1,3-dipole is an organic molecule that can be represented as either an allyl-type or a propargyl/allenyl-type zwitterionic octet/sextet structures. Both types of 1,3-dipoles share four electrons in the π-system over three atoms. The allyl-type is bent whereas the propargyl/allenyl-type is linear in geometry. 1,3-Dipo... | [
"1,3-Dipolar cycloaddition — Reactivity\n\nConjugation, especially with aromatic groups, increases the rate of reaction by stabilization of the transition state. During the transition, the two sigma bonds are being formed at different rates, which may generate partial charges in the transition state that can be sta... |
1,3-Dipolar_cycloaddition_4048062 | Describe the 'Regioselectivity of the 1,3-dipolar cycloaddition reaction mediated by metal catalysis of diazocarbonyl compounds' section of the article about '1,3-Dipolar cycloaddition'. | the carbon proximal to the carbonyl group of the carbonyl ylide and on the methyl propiolate terminal alkyne carbon. The reaction with methyl propargyl ether affords one regioisomer resulting from the HOMOdipolarophile-LUMOdipole interaction, which has largest coefficients on the carbon distal to the carbonyl group of ... | [
"1,3-Dipolar cycloaddition — Reactivity\n\nConjugation, especially with aromatic groups, increases the rate of reaction by stabilization of the transition state. During the transition, the two sigma bonds are being formed at different rates, which may generate partial charges in the transition state that can be sta... |
1,3-Dipolar_cycloaddition_4048045 | Reconstruct the content about 'With respect to dipole' from the article on '1,3-Dipolar cycloaddition'. | Generally, the stereochemistry of the dipole is not of major concern because only few dipoles could form stereogenic centers, and resonance structures allow bond rotation which scrambles the stereochemistry. However, the study of azomethine ylides has verified that cycloaddition is also stereospecific with respect to t... | [
"1,3-Dipolar cycloaddition — Reactivity\n\nConjugation, especially with aromatic groups, increases the rate of reaction by stabilization of the transition state. During the transition, the two sigma bonds are being formed at different rates, which may generate partial charges in the transition state that can be sta... |
1,3-Dipolar_cycloaddition_4048039 | What information does the article about '1,3-Dipolar cycloaddition' provide on 'Type II'? | HOMO of the dipole can pair with LUMO of the dipolarophile; alternatively, HOMO of the dipolarophile can pair with LUMO of the dipole. This two-way interaction arises because the energy gap in either direction is similar. A dipole of this class is referred to as a HOMO-LUMO-controlled dipole or an ambiphilic dipole, wh... | [
"1,3-Dipolar cycloaddition — Reactivity\n\nConjugation, especially with aromatic groups, increases the rate of reaction by stabilization of the transition state. During the transition, the two sigma bonds are being formed at different rates, which may generate partial charges in the transition state that can be sta... |
1,3-Dipolar_cycloaddition_4048054 | What information does the article about '1,3-Dipolar cycloaddition' provide on 'Preparation of carbonyl ylides for 1,3-dipolar cycloaddition reactions'? | Ylides are regarded as positively charged heteroatoms connected to negatively charged carbon atoms, which include ylides of sulfonium, thiocarbonyl, oxonium, nitrogen, and carbonyl. Several methods exist for generating carbonyl ylides, which are necessary intermediates for generating oxygen-containing five-membered rin... | [
"1,3-Dipolar cycloaddition — Reactivity\n\nConjugation, especially with aromatic groups, increases the rate of reaction by stabilization of the transition state. During the transition, the two sigma bonds are being formed at different rates, which may generate partial charges in the transition state that can be sta... |
1,3-Dipolar_cycloaddition_4048063 | What information does the article about '1,3-Dipolar cycloaddition' provide on 'Stereoselectivity and asymmetric induction of the 1,3-dipolar cycloaddition reaction mediated by metal catalysis of diazocarbonyl compounds'? | The stereoselectivity of 1,3-dipolar cycloaddition reactions between carbonyl ylide dipoles and alkenyl dipolarophiles has also been closely examined. For alkynyl dipolarophiles, stereoselectivity is not an issue as relatively planar sp2 carbons are formed, while regioselectivity must be considered (see image of the Pr... | [
"1,3-Dipolar cycloaddition — Reactivity\n\nConjugation, especially with aromatic groups, increases the rate of reaction by stabilization of the transition state. During the transition, the two sigma bonds are being formed at different rates, which may generate partial charges in the transition state that can be sta... |
1,3-Dipolar_cycloaddition_4048065 | What information does the article about '1,3-Dipolar cycloaddition' provide on 'Stereoselectivity and asymmetric induction of the 1,3-dipolar cycloaddition reaction mediated by metal catalysis of diazocarbonyl compounds'? | acids. The first approach employs chiral metal catalysts to modulate the endo and exo stereoselectivity. The chiral catalysts, in particular Rh2[(S)-DOSP]4 and Rh2[(S)-BPTV]4 can induce modest asymmetric induction and was used to synthesize the antifungal agent pseudolaric acid A. This is a result of the chiral metal... | [
"1,3-Dipolar cycloaddition — Reactivity\n\nConjugation, especially with aromatic groups, increases the rate of reaction by stabilization of the transition state. During the transition, the two sigma bonds are being formed at different rates, which may generate partial charges in the transition state that can be sta... |
1,3-Dipolar_cycloaddition_4048053 | Explain what '1,3-Dipolar cycloaddition' covers in the 'Carbonyl ylides' section. | 1,3-dipolar cycloaddition reactions have emerged as powerful tools in the synthesis of complex cyclic scaffolds and molecules for medicinal, biological, and mechanistic studies. Among them, [3+2] cycloaddition reactions involving carbonyl ylides have extensively been employed to generate oxygen-containing five-membered... | [
"1,3-Dipolar cycloaddition — Reactivity\n\nConjugation, especially with aromatic groups, increases the rate of reaction by stabilization of the transition state. During the transition, the two sigma bonds are being formed at different rates, which may generate partial charges in the transition state that can be sta... |
1,3-Dipolar_cycloaddition_4048066 | What information does the article about '1,3-Dipolar cycloaddition' provide on 'Azomethine ylides'? | 1,3-Dipolar cycloaddition between an azomethine ylide and an alkene furnishes an azacyclic structure, such as pyrrolidine. This strategy has been applied to the synthesis of spirotryprostatin A. | [
"1,3-Dipolar cycloaddition — Reactivity\n\nConjugation, especially with aromatic groups, increases the rate of reaction by stabilization of the transition state. During the transition, the two sigma bonds are being formed at different rates, which may generate partial charges in the transition state that can be sta... |
1,3-Dipolar_cycloaddition_4048058 | Reconstruct the content about 'Synthesis of carbonyl ylides from diazomethane derivatives by metal catalysis' from the article on '1,3-Dipolar cycloaddition'. | A universal approach for generating carbonyl ylides involves metal catalysis of α-diazocarbonyl compounds, generally in the presence of dicopper or dirhodium catalysts. After release of nitrogen gas and conversion to the metallocarbene, an intermolecular reaction with a carbonyl group can generate the carbonyl ylide. S... | [
"1,3-Dipolar cycloaddition — Reactivity\n\nConjugation, especially with aromatic groups, increases the rate of reaction by stabilization of the transition state. During the transition, the two sigma bonds are being formed at different rates, which may generate partial charges in the transition state that can be sta... |
1,3-Dipolar_cycloaddition_4048037 | Explain what '1,3-Dipolar cycloaddition' covers in the 'Frontier molecular orbital theory' section. | 1,3-Dipolar cycloadditions are pericyclic reactions, which obey the Dewar-Zimmerman rules and the Woodward–Hoffmann rules. In the Dewar-Zimmerman treatment, the reaction proceeds through a 5-center, zero-node, 6-electron Huckel transition state for this particular molecular orbital diagram. However, each orbital can be... | [
"1,3-Dipolar cycloaddition — Reactivity\n\nConjugation, especially with aromatic groups, increases the rate of reaction by stabilization of the transition state. During the transition, the two sigma bonds are being formed at different rates, which may generate partial charges in the transition state that can be sta... |
1,3-Dipolar_cycloaddition_4048047 | What does the article about '1,3-Dipolar cycloaddition' say regarding 'Directed 1,3-dipolar cycloaddition'? | Trajectory of the cycloaddition can be controlled to achieve a diastereoselective reaction. For example, metals can chelate to the dipolarophile and the incoming dipole and direct the cycloaddition selectively on one face. The example below shows addition of nitrile oxide to an enantiomerically pure allyl alcohol in th... | [
"1,3-Dipolar cycloaddition — Reactivity\n\nConjugation, especially with aromatic groups, increases the rate of reaction by stabilization of the transition state. During the transition, the two sigma bonds are being formed at different rates, which may generate partial charges in the transition state that can be sta... |
1,3-Dipolar_cycloaddition_4048069 | Based on the article about '1,3-Dipolar cycloaddition', describe the 'Copper catalysis' section. | The Huisgen reaction generally does not proceed readily under mild conditions. Meldal et al. and Sharpless et al. independently developed a copper(I)-catalyzed version of the Huisgen reaction, CuAAC (for Copper-catalyzed Azide-Alkyne Cycloaddition), which proceeds very readily in mild, including physiological, conditio... | [
"1,3-Dipolar cycloaddition — Reactivity\n\nConjugation, especially with aromatic groups, increases the rate of reaction by stabilization of the transition state. During the transition, the two sigma bonds are being formed at different rates, which may generate partial charges in the transition state that can be sta... |
1,3-Dipolar_cycloaddition_4048042 | What information does the article about '1,3-Dipolar cycloaddition' provide on 'Reactivity'? | lower gain in sigma bond energy to offset the loss of a pi bond during the transition state. ; Isomerism of the dipolarophile affects reaction rate due to sterics. trans-isomers are more reactive (trans-stilbene will add diphenyl(nitrile imide) 27 times faster than cis-stilbene) because during the reaction, the 120° bo... | [
"1,3-Dipolar cycloaddition — Reactivity\n\nConjugation, especially with aromatic groups, increases the rate of reaction by stabilization of the transition state. During the transition, the two sigma bonds are being formed at different rates, which may generate partial charges in the transition state that can be sta... |
1,3-Dipolar_cycloaddition_4048051 | Summarize the 'Synthetic applications' part of '1,3-Dipolar cycloaddition'. | 1,3-dipolar cycloadditions are important ways toward the synthesis of many important 5-membered heterocycles such as triazoles, furans, isoxazoles, pyrrolidines, and others. Additionally, some cycloadducts can be cleaved to reveal the linear skeleton, providing another route toward the synthesis of aliphatic compounds.... | [
"1,3-Dipolar cycloaddition — Reactivity\n\nConjugation, especially with aromatic groups, increases the rate of reaction by stabilization of the transition state. During the transition, the two sigma bonds are being formed at different rates, which may generate partial charges in the transition state that can be sta... |
1,3-Dipolar_cycloaddition_4048070 | What does the article about '1,3-Dipolar cycloaddition' say regarding 'Strain-promoted cycloaddition'? | To avoid toxicity of copper(I), Bertozzi et al. developed the strain-promoted azide-alkyne cycloaddition (SPAAC) between organic azide and strained cyclooctyne. The angle distortion of the cyclooctyne helps to speed up the reaction by both reducing the activation strain and enhancing the interactions, thereby enabling ... | [
"1,3-Dipolar cycloaddition — Reactivity\n\nConjugation, especially with aromatic groups, increases the rate of reaction by stabilization of the transition state. During the transition, the two sigma bonds are being formed at different rates, which may generate partial charges in the transition state that can be sta... |
1,3-Dipolar_cycloaddition_4048048 | What does the article about '1,3-Dipolar cycloaddition' say regarding 'Regioselectivity'? | For asymmetric dipole-dipolarophile pairs, two regioisomeric products are possible. Both electronic/stereoelectronic and steric factors contribute to the regioselectivity of 1,3-dipolar cycloadditions. | [
"1,3-Dipolar cycloaddition — Reactivity\n\nConjugation, especially with aromatic groups, increases the rate of reaction by stabilization of the transition state. During the transition, the two sigma bonds are being formed at different rates, which may generate partial charges in the transition state that can be sta... |
1,3-Dipolar_cycloaddition_4048030 | Describe the content of the article about '1,3-Dipolar cycloaddition'. | The 1,3-dipolar cycloaddition is a chemical reaction between a 1,3-dipole and a dipolarophile to form a five-membered ring. The earliest 1,3-dipolar cycloadditions were described in the late 19th century to the early 20th century, following the discovery of 1,3-dipoles. Mechanistic investigation and synthetic applicati... | [
"1,3-Dipolar cycloaddition — Reactivity\n\nConjugation, especially with aromatic groups, increases the rate of reaction by stabilization of the transition state. During the transition, the two sigma bonds are being formed at different rates, which may generate partial charges in the transition state that can be sta... |
1,3-Dipolar_cycloaddition_4048061 | From the article on '1,3-Dipolar cycloaddition', restate the 'Regioselectivity of the 1,3-dipolar cycloaddition reaction mediated by metal catalysis of diazocarbonyl compounds' content. | Regioselectivity of 1,3-dipolar cycloaddition reactions between carbonyl ylide dipoles and alkynyl or alkenyl dipolarophiles is essential for generating molecules with defined regiochemistry. FMO theory and analysis of the HOMO-LUMO energy gaps between the dipole and dipolarophile can rationalize and predict the regios... | [
"1,3-Dipolar cycloaddition — Reactivity\n\nConjugation, especially with aromatic groups, increases the rate of reaction by stabilization of the transition state. During the transition, the two sigma bonds are being formed at different rates, which may generate partial charges in the transition state that can be sta... |
1,3-Dipolar_cycloaddition_4048067 | From the article on '1,3-Dipolar cycloaddition', restate the 'Ozone' content. | Ozonolysis is a very important organic reaction. Alkenes and alkynes can be cleaved by ozonolysis to give aldehyde, ketone or carboxylic acid products. | [
"1,3-Dipolar cycloaddition — Reactivity\n\nConjugation, especially with aromatic groups, increases the rate of reaction by stabilization of the transition state. During the transition, the two sigma bonds are being formed at different rates, which may generate partial charges in the transition state that can be sta... |
1,3-Dipolar_cycloaddition_4048043 | What does the article about '1,3-Dipolar cycloaddition' say regarding 'Stereospecificity'? | 1,3-dipolar cycloadditions usually result in retention of configuration with respect to both the 1,3-dipole and the dipolarophile. Such high degree of stereospecificity is a strong support for the concerted over the stepwise reaction mechanisms. As mentioned before, many examples show that the reactions were stepwise, ... | [
"1,3-Dipolar cycloaddition — Reactivity\n\nConjugation, especially with aromatic groups, increases the rate of reaction by stabilization of the transition state. During the transition, the two sigma bonds are being formed at different rates, which may generate partial charges in the transition state that can be sta... |
1,3-Dipolar_cycloaddition_4048031 | Describe the 'Mechanistic overview' section of the article about '1,3-Dipolar cycloaddition'. | Originally two proposed mechanisms describe the 1,3-dipolar cycloaddition: first, the concerted pericyclic cycloaddition mechanism, proposed by Rolf Huisgen; and second, the stepwise mechanism involving a diradical intermediate, proposed by Firestone. After much debate, the former proposal is now generally accepted —th... | [
"1,3-Dipolar cycloaddition — Reactivity\n\nConjugation, especially with aromatic groups, increases the rate of reaction by stabilization of the transition state. During the transition, the two sigma bonds are being formed at different rates, which may generate partial charges in the transition state that can be sta... |
1,3-Dipolar_cycloaddition_4048050 | What information does the article about '1,3-Dipolar cycloaddition' provide on 'Steric effect'? | Steric effects can either cooperate or compete with the aforementioned electronic effects. Sometimes steric effects completely outweighs the electronic preference, giving the opposite regioisomer exclusively. For example, diazomethane generally adds to methyl acrylate to give 3-carboxyl pyrazoline. However, by putting ... | [
"1,3-Dipolar cycloaddition — Reactivity\n\nConjugation, especially with aromatic groups, increases the rate of reaction by stabilization of the transition state. During the transition, the two sigma bonds are being formed at different rates, which may generate partial charges in the transition state that can be sta... |
1,3-Dipolar_cycloaddition_4048032 | What information does the article about '1,3-Dipolar cycloaddition' provide on 'Pericyclic mechanism'? | Substituent effects: Different substituents on the dipole do not exhibit a large effect on the cycloaddition rate, suggesting that the reaction does not involve a charge-separated intermediate. ; Solvent effects: Solvent polarity has little effect on the cycloaddition rate, in line with the pericyclic mechanism where p... | [
"1,3-Dipolar cycloaddition — Reactivity\n\nConjugation, especially with aromatic groups, increases the rate of reaction by stabilization of the transition state. During the transition, the two sigma bonds are being formed at different rates, which may generate partial charges in the transition state that can be sta... |
1,3-Dipolar_cycloaddition_4048046 | What does the article about '1,3-Dipolar cycloaddition' say regarding 'Diastereoselectivity'? | When two or more stereocenters are generated during the reaction, diastereomeric transition states and products can be obtained. In the Diels-Alder cycloaddition, the endo diastereoselectivity due to secondary orbital interactions is usually observed. In 1,3-dipolar cycloadditions, however, two forces influence the dia... | [
"1,3-Dipolar cycloaddition — Reactivity\n\nConjugation, especially with aromatic groups, increases the rate of reaction by stabilization of the transition state. During the transition, the two sigma bonds are being formed at different rates, which may generate partial charges in the transition state that can be sta... |
1,3-Dipolar_cycloaddition_4048036 | What information does the article about '1,3-Dipolar cycloaddition' provide on 'Solvent effects'? | 1,3-dipolar cycloadditions experience very little solvent effect because both the reactants and the transition states are generally non-polar. For example, the rate of reaction between phenyl diazomethane and ethyl acrylate or norbornene (see scheme below) changes only slightly upon varying solvents from cyclohexane to... | [
"1,3-Dipolar cycloaddition — Reactivity\n\nConjugation, especially with aromatic groups, increases the rate of reaction by stabilization of the transition state. During the transition, the two sigma bonds are being formed at different rates, which may generate partial charges in the transition state that can be sta... |
1,3-Indandione_25447842 | Summarize the 'Chemical properties' part of '1,3-Indandione'. | Bindone-formation.svg Bromination 1,3-Indanediol.svg Partial Reduction 1,3-Indanedione.svg Reduction 1,3-Indanedione.svg The carbon at the C-2 position is alpha to both carbonyls, and thus can act as a nucleophile. It undergoes self-aldol condensation quite easily, resulting in bindone. Bromination occurs at the 2-pos... | [
"1,3-Indandione — Chemical properties\n\nBindone-formation.svg Bromination 1,3-Indanediol.svg Partial Reduction 1,3-Indanedione.svg Reduction 1,3-Indanedione.svg The carbon at the C-2 position is alpha to both carbonyls, and thus can act as a nucleophile. It undergoes self-aldol condensation quite easily, resulting... |
1,3-Indandione_25447840 | Based on the article about '1,3-Indandione', describe the 'Structural properties' section. | In the solid state, 1,3-indandione occurs as a diketone; in water, it is partially (~2%) enolized. The enolate anion exhibits significant delocalization, and the highest electron density is on the second carbon. This explains many of chemical properties of the compound. | [
"1,3-Indandione — Chemical properties\n\nBindone-formation.svg Bromination 1,3-Indanediol.svg Partial Reduction 1,3-Indanedione.svg Reduction 1,3-Indanedione.svg The carbon at the C-2 position is alpha to both carbonyls, and thus can act as a nucleophile. It undergoes self-aldol condensation quite easily, resulting... |
1,3-Indandione_25447839 | Summarize the following section from the article on '1,3-Indandione'. | 1,3-Indandione (sometimes simply indanedione) is an organic compound with the molecular formula C9H6O2. Chemically, it is a β-diketone on an indane framework. In standard conditions it is referred to in different sources as either a colorless or yellowish, green, or (most commonly) yellow solid. | [
"1,3-Indandione — Chemical properties\n\nBindone-formation.svg Bromination 1,3-Indanediol.svg Partial Reduction 1,3-Indanedione.svg Reduction 1,3-Indanedione.svg The carbon at the C-2 position is alpha to both carbonyls, and thus can act as a nucleophile. It undergoes self-aldol condensation quite easily, resulting... |
1,3-Indandione_25447841 | What information does the article about '1,3-Indandione' provide on 'Preparation'? | Indandione-decarboxilation.svg NaECI preparation.svg 1,3-Indandione can be prepared by decarboxylation of the sodium salt of 2-ethoxycarbonyl-1,3-indandione, which itself is obtained by Claisen condensation of ethyl acetate and dimethyl phthalate. | [
"1,3-Indandione — Chemical properties\n\nBindone-formation.svg Bromination 1,3-Indanediol.svg Partial Reduction 1,3-Indanedione.svg Reduction 1,3-Indanedione.svg The carbon at the C-2 position is alpha to both carbonyls, and thus can act as a nucleophile. It undergoes self-aldol condensation quite easily, resulting... |
1,3-Propane_sultone_29238594 | Based on the article about '1,3-Propane sultone', describe the 'Reactions' section. | Propane-1,3-sultone hydrolysis.svg 1,3-propane sultone is an activated ester and is susceptible to nucleophilic attack. It hydrolyzes to the acid. It has been used in the synthesis of specialist surfactants, such as CHAPS detergent. | [
"1,3-Propane sultone — Reactions\n\nPropane-1,3-sultone hydrolysis.svg 1,3-propane sultone is an activated ester and is susceptible to nucleophilic attack. It hydrolyzes to the acid. It has been used in the synthesis of specialist surfactants, such as CHAPS detergent.",
"1,3-Propane sultone — Synthesis\n\nIt may... |
1,3-Propane_sultone_29238592 | Describe the content of the article about '1,3-Propane sultone'. | 1,3-Propane sultone is the organosulfur compound with the formula (CH2)3SO3. It is a cyclic sulfonate ester, a class of compounds called sultones. It is a readily melting colorless solid. | [
"1,3-Propane sultone — Reactions\n\nPropane-1,3-sultone hydrolysis.svg 1,3-propane sultone is an activated ester and is susceptible to nucleophilic attack. It hydrolyzes to the acid. It has been used in the synthesis of specialist surfactants, such as CHAPS detergent.",
"1,3-Propane sultone — Synthesis\n\nIt may... |
1,3-Propanediol_22044823 | What does the article about '1,3-Propanediol' say regarding 'Products'? | It is mainly used as a building block in the production of polymers such as polytrimethylene terephthalate. 1,3-Propanediol can be formulated into a variety of industrial products including composites, adhesives, laminates, coatings, moldings, aliphatic polyesters, copolyesters. It is also a common solvent. It is used ... | [
"1,3-Propanediol — Products\n\nIt is mainly used as a building block in the production of polymers such as polytrimethylene terephthalate. 1,3-Propanediol can be formulated into a variety of industrial products including composites, adhesives, laminates, coatings, moldings, aliphatic polyesters, copolyesters. It is... |
1,3-Propanediol_22044822 | Reconstruct the content from the article about '1,3-Propanediol'. | 1,3-Propanediol is the organic compound with the formula CH2(CH2OH)2. This 3-carbon diol is a colorless viscous liquid that is miscible with water. | [
"1,3-Propanediol — Products\n\nIt is mainly used as a building block in the production of polymers such as polytrimethylene terephthalate. 1,3-Propanediol can be formulated into a variety of industrial products including composites, adhesives, laminates, coatings, moldings, aliphatic polyesters, copolyesters. It is... |
1,3-Propanediol_22044824 | Explain what '1,3-Propanediol' covers in the 'Production' section. | Conversion from glucose effected by a genetically modified strain of E. coli by DuPont Tate & Lyle BioProducts (See: bioseparation of 1,3-propanediol). An estimated 120,000 tons were produced in 2007". According to DuPont, the Bio-PDO process uses 40% less energy than conventional processes, Because of DuPont and Tate ... | [
"1,3-Propanediol — Products\n\nIt is mainly used as a building block in the production of polymers such as polytrimethylene terephthalate. 1,3-Propanediol can be formulated into a variety of industrial products including composites, adhesives, laminates, coatings, moldings, aliphatic polyesters, copolyesters. It is... |
1,4,7-Triazacyclononane_8007969 | What does the article about '1,4,7-Triazacyclononane' say regarding 'Coordination chemistry'? | TACN is a popular tridentate ligand. It is threefold symmetric and binds to one face of an octahedron of metalloids and transition metals. The (TACN)M unit is kinetically inert, allowing further synthetic transformations on the other coordination sites. A bulky analogue of TACN, is the N,N',N"-trimethylated analogue tr... | [
"1,4,7-Triazacyclononane — Coordination chemistry\n\nTACN is a popular tridentate ligand. It is threefold symmetric and binds to one face of an octahedron of metalloids and transition metals. The (TACN)M unit is kinetically inert, allowing further synthetic transformations on the other coordination sites. A bulky a... |
1,4,7-Triazacyclononane_8007968 | From the article on '1,4,7-Triazacyclononane', restate the 'Synthesis' content. | H2NCH2CH2NHCH2CH2NH2 + 3 TsCl → Ts(H)NCH2CH2N(Ts)CH2CHH2N(H)Ts + 3 HCl ; Ts(H)NCH2CH2N(Ts)CH2CH2N(H)Ts + 2 NaOEt → Ts(Na)NCH2CH2N(Ts)CH2CH2N(Na)Ts ; Ts(Na)NCHH2CH2N(Ts)CH2CH2N(Na)Ts + TsOCH2CH2OTs + → [(CH2CH2N(Ts)]3 + 2 NaOTs ; [(CH2CH2N(Ts)]3 + 3 H2O → [CH2CH2NH]3 + 3 HOTs The ligand is prepared from... | [
"1,4,7-Triazacyclononane — Coordination chemistry\n\nTACN is a popular tridentate ligand. It is threefold symmetric and binds to one face of an octahedron of metalloids and transition metals. The (TACN)M unit is kinetically inert, allowing further synthetic transformations on the other coordination sites. A bulky a... |
1,4,7-Triazacyclononane_8007967 | Reconstruct the content from the article about '1,4,7-Triazacyclononane'. | 1,4,7-Triazacyclononane, known as "TACN" which is pronounced "tack-en," is an aza-crown ether with the formula (C2H4NH)3. TACN is derived, formally speaking, from cyclononane by replacing three equidistant CH2 groups with NH groups. TACN is one of the oligomers derived from aziridine, C2H4NH. Other members of the serie... | [
"1,4,7-Triazacyclononane — Coordination chemistry\n\nTACN is a popular tridentate ligand. It is threefold symmetric and binds to one face of an octahedron of metalloids and transition metals. The (TACN)M unit is kinetically inert, allowing further synthetic transformations on the other coordination sites. A bulky a... |
1,4-Benzoquinone_25432635 | Describe the 'Structure and redox' section of the article about '1,4-Benzoquinone'. | Benzoquinone is a planar molecule with localized, alternating C=C, C=O, and C–C bonds. Reduction gives the semiquinone anion C6H4O2−}, which adopts a more delocalized structure. Further reduction coupled to protonation gives the hydroquinone, wherein the C6 ring is fully delocalized. | [
"1,4-Benzoquinone — Structure and redox\n\nBenzoquinone is a planar molecule with localized, alternating C=C, C=O, and C–C bonds. Reduction gives the semiquinone anion C6H4O2−}, which adopts a more delocalized structure. Further reduction coupled to protonation gives the hydroquinone, wherein the C6 ring is fully d... |
1,4-Benzoquinone_25432636 | Describe the 'Reactions and applications' section of the article about '1,4-Benzoquinone'. | Quinone is mainly used as a precursor to hydroquinone, which is used in photography and rubber manufacture as a reducing agent and antioxidant. Benzoquinonium is a skeletal muscle relaxant, ganglion blocking agent that is made from benzoquinone. | [
"1,4-Benzoquinone — Structure and redox\n\nBenzoquinone is a planar molecule with localized, alternating C=C, C=O, and C–C bonds. Reduction gives the semiquinone anion C6H4O2−}, which adopts a more delocalized structure. Further reduction coupled to protonation gives the hydroquinone, wherein the C6 ring is fully d... |
1,4-Benzoquinone_25432639 | Summarize the 'Related 1,4-benzoquinones' part of '1,4-Benzoquinone'. | 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) is a stronger oxidant and dehydrogenation agent than 1,4-benzoquinone. Chloranil 1,4-C6Cl4O2 is another potent oxidant and dehydrogenation agent. Monochloro-p-benzoquinone is yet another but milder oxidant. | [
"1,4-Benzoquinone — Structure and redox\n\nBenzoquinone is a planar molecule with localized, alternating C=C, C=O, and C–C bonds. Reduction gives the semiquinone anion C6H4O2−}, which adopts a more delocalized structure. Further reduction coupled to protonation gives the hydroquinone, wherein the C6 ring is fully d... |
1,4-Benzoquinone_25432640 | What information does the article about '1,4-Benzoquinone' provide on 'Metabolism'? | 1,4-Benzoquinone is a toxic metabolite found in human blood and can be used to track exposure to benzene or mixtures containing benzene and benzene compounds, such as petrol. The compound can interfere with cellular respiration, and kidney damage has been found in animals receiving severe exposure. It is excreted in it... | [
"1,4-Benzoquinone — Structure and redox\n\nBenzoquinone is a planar molecule with localized, alternating C=C, C=O, and C–C bonds. Reduction gives the semiquinone anion C6H4O2−}, which adopts a more delocalized structure. Further reduction coupled to protonation gives the hydroquinone, wherein the C6 ring is fully d... |
1,4-Benzoquinone_25432633 | Describe the content of the article about '1,4-Benzoquinone'. | 1,4-Benzoquinone, commonly known as para-quinone, is a chemical compound with the formula C6H4O2. In a pure state, it forms bright-yellow crystals with a characteristic irritating odor, resembling that of chlorine, bleach, and hot plastic or formaldehyde. This six-membered ring compound is the oxidized derivative of 1,... | [
"1,4-Benzoquinone — Structure and redox\n\nBenzoquinone is a planar molecule with localized, alternating C=C, C=O, and C–C bonds. Reduction gives the semiquinone anion C6H4O2−}, which adopts a more delocalized structure. Further reduction coupled to protonation gives the hydroquinone, wherein the C6 ring is fully d... |
1,4-Benzoquinone_25432641 | Describe the 'Safety' section of the article about '1,4-Benzoquinone'. | 1,4-Benzoquinone is able to stain skin dark brown, cause erythema (redness, rashes on skin) and lead on to localized tissue necrosis. It is particularly irritating to the eyes and respiratory system. Its ability to sublime at commonly encountered temperatures allows for a greater airborne exposure risk than might be ex... | [
"1,4-Benzoquinone — Structure and redox\n\nBenzoquinone is a planar molecule with localized, alternating C=C, C=O, and C–C bonds. Reduction gives the semiquinone anion C6H4O2−}, which adopts a more delocalized structure. Further reduction coupled to protonation gives the hydroquinone, wherein the C6 ring is fully d... |
1,4-Benzoquinone_25432634 | What does the article about '1,4-Benzoquinone' say regarding 'Preparation'? | C6H4(CHMe2)2 + 3 O2 → C6H4O2 + 2 OCMe2 + H2O 1,4-Benzoquinone is prepared industrially by oxidation of hydroquinone, which can be obtained by several routes. One route involves oxidation of diisopropylbenzene and the Hock rearrangement. The net reaction can be represented as follows: The reaction proceeds via ... | [
"1,4-Benzoquinone — Structure and redox\n\nBenzoquinone is a planar molecule with localized, alternating C=C, C=O, and C–C bonds. Reduction gives the semiquinone anion C6H4O2−}, which adopts a more delocalized structure. Further reduction coupled to protonation gives the hydroquinone, wherein the C6 ring is fully d... |
1,4-Benzoquinone_25432638 | Explain what '1,4-Benzoquinone' covers in the 'Organic synthesis' section. | An acidic potassium iodide solution reduces a solution of benzoquinone to hydroquinone, which can be reoxidized back to the quinone with a solution of silver nitrate. Due to its ability to function as an oxidizer, 1,4-benzoquinone can be found in methods using the Wacker-Tsuji oxidation, wherein a palladium salt cataly... | [
"1,4-Benzoquinone — Structure and redox\n\nBenzoquinone is a planar molecule with localized, alternating C=C, C=O, and C–C bonds. Reduction gives the semiquinone anion C6H4O2−}, which adopts a more delocalized structure. Further reduction coupled to protonation gives the hydroquinone, wherein the C6 ring is fully d... |
1,4-Benzoquinone_25432637 | Based on the article about '1,4-Benzoquinone', describe the 'Organic synthesis' section. | ThieleReaction.svg It is used as a hydrogen acceptor and oxidant in organic synthesis. 1,4-Benzoquinone serves as a dehydrogenation reagent. It is also used as a dienophile in Diels Alder reactions. Benzoquinone reacts with acetic anhydride and sulfuric acid to give the triacetate of hydroxyquinol. This reaction is cal... | [
"1,4-Benzoquinone — Structure and redox\n\nBenzoquinone is a planar molecule with localized, alternating C=C, C=O, and C–C bonds. Reduction gives the semiquinone anion C6H4O2−}, which adopts a more delocalized structure. Further reduction coupled to protonation gives the hydroquinone, wherein the C6 ring is fully d... |
1,4-Bis(diphenylphosphino)butane_21252800 | Summarize the 'Coordination complexes' part of '1,4-Bis(diphenylphosphino)butane'. | Nickel complexes in which the ligand is bidentate or monodentate are known. Palladium complexes containing dppb are used in a variety of catalytic reactions. The ligand's natural bite angle is 94° in its bidentate coordination mode. | [
"1,4-Bis(diphenylphosphino)butane — Coordination complexes\n\nNickel complexes in which the ligand is bidentate or monodentate are known. Palladium complexes containing dppb are used in a variety of catalytic reactions. The ligand's natural bite angle is 94° in its bidentate coordination mode.",
"1,4-Bis(diphenyl... |
1,4-Bis(diphenylphosphino)butane_21252799 | Describe the content of the article about '1,4-Bis(diphenylphosphino)butane'. | 1,4-Bis(diphenylphosphino)butane (dppb) is an organophosphorus compound with the formula (Ph2PCH2CH2)2. It is less commonly used in coordination chemistry than other diphosphine ligands such as dppe. It is a white solid that is soluble in organic solvents. | [
"1,4-Bis(diphenylphosphino)butane — Coordination complexes\n\nNickel complexes in which the ligand is bidentate or monodentate are known. Palladium complexes containing dppb are used in a variety of catalytic reactions. The ligand's natural bite angle is 94° in its bidentate coordination mode.",
"1,4-Bis(diphenyl... |
1,4-Butane_sultone_21273763 | Reconstruct the content from the article about '1,4-Butane sultone'. | 1,4-butane sultone is a six-membered δ-sultone and the cyclic ester of 4-hydroxybutanesulfonic acid. As a sulfo-alkylating agent, 1,4-butanesultone is used to introduce the sulfobutyl group (–(CH2)4–SO3−) into hydrophobic compounds possessing nucleophilic functional groups, for example hydroxy groups (as in the case of... | [
"1,4-Butane sultone\n\n1,4-butane sultone is a six-membered δ-sultone and the cyclic ester of 4-hydroxybutanesulfonic acid. As a sulfo-alkylating agent, 1,4-butanesultone is used to introduce the sulfobutyl group (–(CH2)4–SO3−) into hydrophobic compounds possessing nucleophilic functional groups, for example hydrox... |
1,4-Butane_sultone_21273768 | Explain what '1,4-Butane sultone' covers in the 'Ionic liquids' section. | The ionic liquid 4-triethylammonium butane-1-sulfonic acid hydrogensulfate (TEBSA HSO4) is formed by the reaction of 1,4-butanesultone with triethylamine in acetonitrile to the zwitterion (85% yield) and subsequent reaction with concentrated sulfuric acid. 4-triethylammonium butane-1-sulfonic acid hydrogensulfate can ... | [
"1,4-Butane sultone\n\n1,4-butane sultone is a six-membered δ-sultone and the cyclic ester of 4-hydroxybutanesulfonic acid. As a sulfo-alkylating agent, 1,4-butanesultone is used to introduce the sulfobutyl group (–(CH2)4–SO3−) into hydrophobic compounds possessing nucleophilic functional groups, for example hydrox... |
1,4-Butane_sultone_21273764 | From the article on '1,4-Butane sultone', restate the 'Preparation' content. | A lab scale synthesis of 1,4-butanesultone starts from 4,4'-dichlorodibutyl ether (accessible from tetrahydrofuran treated with phosphorus oxychloride and concentrated sulfuric acid), which reacts with sodium sulfite forming the corresponding 4,4'-butanedisulfonic disodium salt. By passing it through an acidic ion exch... | [
"1,4-Butane sultone\n\n1,4-butane sultone is a six-membered δ-sultone and the cyclic ester of 4-hydroxybutanesulfonic acid. As a sulfo-alkylating agent, 1,4-butanesultone is used to introduce the sulfobutyl group (–(CH2)4–SO3−) into hydrophobic compounds possessing nucleophilic functional groups, for example hydrox... |
1,4-Butane_sultone_21273769 | From the article on '1,4-Butane sultone', restate the 'Sulfobutylated β-cyclodextrin' content. | Already in 1949 the reaction of 1,4-butanesultone with the water-insoluble polysaccharide cellulose in sodium hydroxide solution was reported, which leads to a water-soluble product. Derived from this the derivatization of β-cyclodextrin to sulfobutyl ether-beta-cyclodextrin (SBECD) is by now an important application o... | [
"1,4-Butane sultone\n\n1,4-butane sultone is a six-membered δ-sultone and the cyclic ester of 4-hydroxybutanesulfonic acid. As a sulfo-alkylating agent, 1,4-butanesultone is used to introduce the sulfobutyl group (–(CH2)4–SO3−) into hydrophobic compounds possessing nucleophilic functional groups, for example hydrox... |
1,4-Butane_sultone_21273765 | Reconstruct the content about 'Preparation' from the article on '1,4-Butane sultone'. | in aqueous solution proceeds particularly efficiently when heated with high-boiling, water-immiscible solvents (for example 1,2-dichlorobenzene or diethylbenzene, both boiling at about 180 °C) in which 1,4-butane-sultone dissolves and is thereby protected from hydrolysis in the aqueous medium. 1,4-butanesultone is obta... | [
"1,4-Butane sultone\n\n1,4-butane sultone is a six-membered δ-sultone and the cyclic ester of 4-hydroxybutanesulfonic acid. As a sulfo-alkylating agent, 1,4-butanesultone is used to introduce the sulfobutyl group (–(CH2)4–SO3−) into hydrophobic compounds possessing nucleophilic functional groups, for example hydrox... |
1,4-Butane_sultone_21273766 | Reconstruct the content about 'Properties' from the article on '1,4-Butane sultone'. | 1,4-butanesultone is a viscous, clear, colorless and odorless liquid which reacts in boiling water (to 4-hydroxybutanesulfonic acid) and alcohols (to 4-alkoxybutanesulfonic acid) and dissolves in many organic solvents. At temperatures below the melting point, the compound crystallizes giving "large, magnificent plates"... | [
"1,4-Butane sultone\n\n1,4-butane sultone is a six-membered δ-sultone and the cyclic ester of 4-hydroxybutanesulfonic acid. As a sulfo-alkylating agent, 1,4-butanesultone is used to introduce the sulfobutyl group (–(CH2)4–SO3−) into hydrophobic compounds possessing nucleophilic functional groups, for example hydrox... |
1,4-Butanediol_32895525 | What does the article about '1,4-Butanediol' say regarding 'Pharmacodynamics'? | 1,4-Butanediol seems to have two types of pharmacological actions. The major psychoactive effects of 1,4-butanediol are because it is metabolized into GHB; however there is a study suggesting that 1,4-butanediol may have potential alcohol-like pharmacological effects on its own. The study arrived at this conclusion bas... | [
"1,4-Butanediol — Pharmacodynamics\n\n1,4-Butanediol seems to have two types of pharmacological actions. The major psychoactive effects of 1,4-butanediol are because it is metabolized into GHB; however there is a study suggesting that 1,4-butanediol may have potential alcohol-like pharmacological effects on its own... |
1,4-Butanediol_32895521 | Based on the article about '1,4-Butanediol', describe the 'Synthesis' section. | CH3CH2CH2CH3 + O2 → HOCH2CH2CH2CH2OH Tellurium oxide-containing catalysts are used for the oxidation of butane: In another industrial synthesis, acetylene reacts with two equivalents of formaldehyde to form 1,4-butynediol. Hydrogenation of 1,4-butynediol gives 1,4-butanediol. It is also manufactured on an industrial sc... | [
"1,4-Butanediol — Pharmacodynamics\n\n1,4-Butanediol seems to have two types of pharmacological actions. The major psychoactive effects of 1,4-butanediol are because it is metabolized into GHB; however there is a study suggesting that 1,4-butanediol may have potential alcohol-like pharmacological effects on its own... |
1,4-Butanediol_32895527 | Describe the '2007 contamination of Bindeez toy' section of the article about '1,4-Butanediol'. | A toy called "Bindeez" ("Aqua Dots" in North America) was recalled by the distributor in November 2007 because of the presence of 1,4-butanediol. The toy consists of small beads that stick to each other by sprinkling water. 1,4-Butanediol was detected by GC-MS. The production plant seems to have intended to cut costs b... | [
"1,4-Butanediol — Pharmacodynamics\n\n1,4-Butanediol seems to have two types of pharmacological actions. The major psychoactive effects of 1,4-butanediol are because it is metabolized into GHB; however there is a study suggesting that 1,4-butanediol may have potential alcohol-like pharmacological effects on its own... |
1,4-Butanediol_32895523 | What information does the article about '1,4-Butanediol' provide on 'Use as a recreational drug'? | 1,4-Butanediol is also used as a recreational drug known by some users as "One Comma Four", "Liquid Fantasy", "One Four Bee" or "One Four B-D-O". It exerts effects similar to γ-hydroxybutyrate (GHB), which is a metabolic product of 1,4-butanediol. | [
"1,4-Butanediol — Pharmacodynamics\n\n1,4-Butanediol seems to have two types of pharmacological actions. The major psychoactive effects of 1,4-butanediol are because it is metabolized into GHB; however there is a study suggesting that 1,4-butanediol may have potential alcohol-like pharmacological effects on its own... |
1,4-Butanediol_32895520 | Reconstruct the content from the article about '1,4-Butanediol'. | 1,4-Butanediol, colloquially known as BD or BDO, is a primary alcohol, and an organic compound, with the formula HOCH2CH2CH2CH2OH. It is a colorless viscous liquid. It is one of four stable isomers of butanediol. | [
"1,4-Butanediol — Pharmacodynamics\n\n1,4-Butanediol seems to have two types of pharmacological actions. The major psychoactive effects of 1,4-butanediol are because it is metabolized into GHB; however there is a study suggesting that 1,4-butanediol may have potential alcohol-like pharmacological effects on its own... |
1,4-Butanediol_32895528 | Explain what '1,4-Butanediol' covers in the '2021 poisoning at Darmstadt Technical University' section. | In August 2021, several people fell severely ill after consuming drinks at building L2.01 at the Lichtwiese Campus of Darmstadt Technical University, Germany. Seven showed severe symptoms, two were transported to a hospital in Frankfurt, and a 30 year old person was, for a time, in a critical state. 1,4-butanediol had ... | [
"1,4-Butanediol — Pharmacodynamics\n\n1,4-Butanediol seems to have two types of pharmacological actions. The major psychoactive effects of 1,4-butanediol are because it is metabolized into GHB; however there is a study suggesting that 1,4-butanediol may have potential alcohol-like pharmacological effects on its own... |
1,4-Butanediol_32895526 | Explain what '1,4-Butanediol' covers in the 'Legality' section. | While 1,4-butanediol is not currently scheduled federally in the United States, a number of states have classified 1,4-butanediol as a controlled substance. Individuals have been prosecuted for 1,4-butanediol under the Federal Analog Act as substantially similar to GHB. A federal case in New York in 2002 ruled that 1,4... | [
"1,4-Butanediol — Pharmacodynamics\n\n1,4-Butanediol seems to have two types of pharmacological actions. The major psychoactive effects of 1,4-butanediol are because it is metabolized into GHB; however there is a study suggesting that 1,4-butanediol may have potential alcohol-like pharmacological effects on its own... |
1,4-Butanediol_32895524 | Summarize the 'Pharmacokinetics' part of '1,4-Butanediol'. | 1,4-Butanediol is converted into GHB by the enzymes alcohol dehydrogenase and aldehyde dehydrogenase, and differing levels of these enzymes may account for differences in effects and side effects between users. While co-administration of ethanol and GHB already poses serious risks, co-administration of ethanol with 1,4... | [
"1,4-Butanediol — Pharmacodynamics\n\n1,4-Butanediol seems to have two types of pharmacological actions. The major psychoactive effects of 1,4-butanediol are because it is metabolized into GHB; however there is a study suggesting that 1,4-butanediol may have potential alcohol-like pharmacological effects on its own... |
1,4-Butynediol_10036516 | What does the article about '1,4-Butynediol' say regarding 'Applications'? | 1,4-Butynediol is a precursor to 1,4-butanediol and 2-butene-1,4-diol by hydrogenation. It is also used in the manufacture of certain herbicides, textile additives, corrosion inhibitors, plasticizers, synthetic resins, and polyurethanes. It is the major raw material used in the synthesis of vitamin B6. It is also used ... | [
"1,4-Butynediol — Safety\n\n1,4-Butynediol is corrosive and irritates the skin, eyes, and respiratory tract.",
"1,4-Butynediol — Applications\n\n1,4-Butynediol is a precursor to 1,4-butanediol and 2-butene-1,4-diol by hydrogenation. It is also used in the manufacture of certain herbicides, textile additives, corr... |
1,4-Butynediol_10036515 | Reconstruct the content about 'Synthesis' from the article on '1,4-Butynediol'. | 2 CH2O + HC≡CH → HOCH2CCCH2OH 1,4-Butynediol can be produced in the Reppe synthesis, where formaldehyde and acetylene are the reactants: Several patented production methods use copper bismuth catalysts coated on an inert material. The normal temperature range for the reaction is 90 °C up to 150 °C, depending on the ... | [
"1,4-Butynediol — Safety\n\n1,4-Butynediol is corrosive and irritates the skin, eyes, and respiratory tract.",
"1,4-Butynediol — Applications\n\n1,4-Butynediol is a precursor to 1,4-butanediol and 2-butene-1,4-diol by hydrogenation. It is also used in the manufacture of certain herbicides, textile additives, corr... |
1,4-Butynediol_10036514 | Describe the content of the article about '1,4-Butynediol'. | 1,4-Butynediol is an organic compound that is an alkyne and a diol. It is a colourless, hygroscopic solid that is soluble in water and polar organic solvents. It is a commercially significant compound in its own right and as a precursor to other products. | [
"1,4-Butynediol — Safety\n\n1,4-Butynediol is corrosive and irritates the skin, eyes, and respiratory tract.",
"1,4-Butynediol — Applications\n\n1,4-Butynediol is a precursor to 1,4-butanediol and 2-butene-1,4-diol by hydrogenation. It is also used in the manufacture of certain herbicides, textile additives, corr... |
1,4-Dichlorobenzene_2878605 | Reconstruct the content about 'Environmental and health effects' from the article on '1,4-Dichlorobenzene'. | p-DCB is poorly soluble in water and is not easily broken down by soil organisms. Like many hydrocarbons, p-DCB is lipophilic and will accumulate in fatty tissues if consumed by a person or animal. The United States Department of Health and Human Services (DHHS) and the International Agency for Research on Cancer (IARC... | [
"1,4-Dichlorobenzene — Environmental and health effects\n\np-DCB is poorly soluble in water and is not easily broken down by soil organisms. Like many hydrocarbons, p-DCB is lipophilic and will accumulate in fatty tissues if consumed by a person or animal. The United States Department of Health and Human Services (... |
1,4-Dichlorobenzene_2878604 | What does the article about '1,4-Dichlorobenzene' say regarding 'Precursor to other chemicals'? | Synthesis Poly(p-phenylene sulfide).svg Nitration gives 1,4-dichloronitrobenzene, a precursor to commercial dyes and pigments. The chloride sites on p-DCB can be substituted with hydroxylamine and sulfide groups. In a growing application, p-DCB is the precursor to the high performance polymer poly(p-phenylene sulfide): | [
"1,4-Dichlorobenzene — Environmental and health effects\n\np-DCB is poorly soluble in water and is not easily broken down by soil organisms. Like many hydrocarbons, p-DCB is lipophilic and will accumulate in fatty tissues if consumed by a person or animal. The United States Department of Health and Human Services (... |
1,4-Dichlorobenzene_2878602 | Reconstruct the content about 'Production' from the article on '1,4-Dichlorobenzene'. | C6H6 + 2 Cl2 → C6H4Cl2 + 2 HCl p-DCB is produced by chlorination of benzene using ferric chloride as a catalyst: The chief impurity is the 1,2 isomer. The compound can be purified by fractional crystallization, taking advantage of its relatively high melting point of 53.5 °C; the isomeric dichlorobenzenes and chlo... | [
"1,4-Dichlorobenzene — Environmental and health effects\n\np-DCB is poorly soluble in water and is not easily broken down by soil organisms. Like many hydrocarbons, p-DCB is lipophilic and will accumulate in fatty tissues if consumed by a person or animal. The United States Department of Health and Human Services (... |
1,4-Dichlorobenzene_2878603 | What information does the article about '1,4-Dichlorobenzene' provide on 'Disinfectant, deodorant, and pesticide'? | p-DCB is used to control moths, molds, and mildew. It also finds use as a disinfectant in waste containers and restrooms and is the characteristic smell associated with urinal cakes. Its usefulness for these applications arises from p-DCB's low solubility in water and its relatively high volatility: it sublimes readily... | [
"1,4-Dichlorobenzene — Environmental and health effects\n\np-DCB is poorly soluble in water and is not easily broken down by soil organisms. Like many hydrocarbons, p-DCB is lipophilic and will accumulate in fatty tissues if consumed by a person or animal. The United States Department of Health and Human Services (... |
1,4-Dichlorobenzene_2878601 | What information does the article about '1,4-Dichlorobenzene' provide? | 1,4-Dichlorobenzene (1,4-DCB, p-DCB, or para-dichlorobenzene, sometimes abbreviated as PDCB or para) is an organic compound with the formula C6H4Cl2. This colorless solid has a strong odor. The molecule consists of a benzene ring with two chlorine atoms (replacing hydrogen atoms) on opposing sites of the ring. It is us... | [
"1,4-Dichlorobenzene — Environmental and health effects\n\np-DCB is poorly soluble in water and is not easily broken down by soil organisms. Like many hydrocarbons, p-DCB is lipophilic and will accumulate in fatty tissues if consumed by a person or animal. The United States Department of Health and Human Services (... |
1,4-Dihydroxyanthraquinone_17035007 | Reconstruct the content from the article about '1,4-Dihydroxyanthraquinone'. | 1,4-Dihydroxyanthraquinone, also called quinizarin or Solvent Orange 86, is an organic compound derived from anthroquinone. Quinizarin is an orange or red-brown crystalline powder. It is formally derived from anthraquinone by replacement of two hydrogen atoms by hydroxyl (OH) groups. It is one of ten dihydroxyanthraqui... | [
"1,4-Dihydroxyanthraquinone\n\n1,4-Dihydroxyanthraquinone, also called quinizarin or Solvent Orange 86, is an organic compound derived from anthroquinone. Quinizarin is an orange or red-brown crystalline powder. It is formally derived from anthraquinone by replacement of two hydrogen atoms by hydroxyl (OH) groups. ... |
1,4-Dihydroxyanthraquinone_17035008 | Explain what '1,4-Dihydroxyanthraquinone' covers in the 'Production' section. | Quinizarin is produced by the reaction of phthalic anhydride and 4-chlorophenol followed by hydrolysis of the chloride: It can also be prepared less efficiently from phthalic anhydride and hydroquinone. | [
"1,4-Dihydroxyanthraquinone\n\n1,4-Dihydroxyanthraquinone, also called quinizarin or Solvent Orange 86, is an organic compound derived from anthroquinone. Quinizarin is an orange or red-brown crystalline powder. It is formally derived from anthraquinone by replacement of two hydrogen atoms by hydroxyl (OH) groups. ... |
1,4-Dihydroxyanthraquinone_17035009 | Describe the 'Uses' section of the article about '1,4-Dihydroxyanthraquinone'. | Quinizarin is an inexpensive dye that is used to colour gasoline and some heating oils. It is used as an intermediate for the synthesis of indanthrene- and alizarin-derived dyes. The OH groups can be replaced by chloride. Chlorination and bromination afford other dyes. Amination (replacement of one OH by ArNH) with ani... | [
"1,4-Dihydroxyanthraquinone\n\n1,4-Dihydroxyanthraquinone, also called quinizarin or Solvent Orange 86, is an organic compound derived from anthroquinone. Quinizarin is an orange or red-brown crystalline powder. It is formally derived from anthraquinone by replacement of two hydrogen atoms by hydroxyl (OH) groups. ... |
1,4-Dimethoxybenzene_18336681 | Based on the article about '1,4-Dimethoxybenzene', describe the 'Occurrence' section. | It occurs naturally in willow (Salix), tea, hyacinth, zucchini (Cucurbita pepo). It appears to attract bees as it has a powerful response in their antenna. In a study in mice, Iranian scientists identified 1,4-dimethoxybenzene as the major psychoactive chemical in musk willow (Salix aegyptiaca) by its ability to cause ... | [
"1,4-Dimethoxybenzene — Occurrence\n\nIt occurs naturally in willow (Salix), tea, hyacinth, zucchini (Cucurbita pepo). It appears to attract bees as it has a powerful response in their antenna. In a study in mice, Iranian scientists identified 1,4-dimethoxybenzene as the major psychoactive chemical in musk willow (... |
1,4-Dimethoxybenzene_18336680 | What information does the article about '1,4-Dimethoxybenzene' provide? | 1,4-Dimethoxybenzene is an organic compound with the formula C6H4(OCH3)2. It is one of three isomers of dimethoxybenzene. It is a white solid with an intensely sweet floral odor. It is produced by several plant species. | [
"1,4-Dimethoxybenzene — Occurrence\n\nIt occurs naturally in willow (Salix), tea, hyacinth, zucchini (Cucurbita pepo). It appears to attract bees as it has a powerful response in their antenna. In a study in mice, Iranian scientists identified 1,4-dimethoxybenzene as the major psychoactive chemical in musk willow (... |
1,4-Dimethoxybenzene_18336684 | Summarize the 'Niche uses' part of '1,4-Dimethoxybenzene'. | It can be used as a developer in black and white film, and as a base in synthesizing catecholamines and phenethylamines. | [
"1,4-Dimethoxybenzene — Occurrence\n\nIt occurs naturally in willow (Salix), tea, hyacinth, zucchini (Cucurbita pepo). It appears to attract bees as it has a powerful response in their antenna. In a study in mice, Iranian scientists identified 1,4-dimethoxybenzene as the major psychoactive chemical in musk willow (... |
1,4-Dimethoxybenzene_18336683 | Summarize the 'Uses' part of '1,4-Dimethoxybenzene'. | 1,4-Dimethoxybenzene is mainly used in perfumes and soaps. It is an intermediate in synthesis of organic compounds, including pharmaceuticals such as methoxamine and butaxamine. | [
"1,4-Dimethoxybenzene — Occurrence\n\nIt occurs naturally in willow (Salix), tea, hyacinth, zucchini (Cucurbita pepo). It appears to attract bees as it has a powerful response in their antenna. In a study in mice, Iranian scientists identified 1,4-dimethoxybenzene as the major psychoactive chemical in musk willow (... |
1,4-Dioxane_14570165 | Summarize the 'Safety' part of '1,4-Dioxane'. | Dioxane has an of 5170 mg/kg in rats. It is irritating to the eyes and respiratory tract. Exposure may cause damage to the central nervous system, liver and kidneys. In a 1978 mortality study conducted on workers exposed to 1,4-dioxane, the observed number deaths from cancer was not significantly different from the exp... | [
"1,4-Dioxane — Safety\n\nDioxane has an of 5170 mg/kg in rats. It is irritating to the eyes and respiratory tract. Exposure may cause damage to the central nervous system, liver and kidneys. In a 1978 mortality study conducted on workers exposed to 1,4-dioxane, the observed number deaths from cancer was not signifi... |
1,4-Dioxane_14570162 | What does the article about '1,4-Dioxane' say regarding 'Trichloroethane transport'? | In the 1980s, most of the dioxane produced was used as a stabilizer for 1,1,1-trichloroethane for storage and transport in aluminium containers. Normally aluminium is protected by a passivating oxide layer, but when these layers are disturbed, the metallic aluminium reacts with trichloroethane to give aluminium trichlo... | [
"1,4-Dioxane — Safety\n\nDioxane has an of 5170 mg/kg in rats. It is irritating to the eyes and respiratory tract. Exposure may cause damage to the central nervous system, liver and kidneys. In a 1978 mortality study conducted on workers exposed to 1,4-dioxane, the observed number deaths from cancer was not signifi... |
1,4-Dioxane_14570167 | What information does the article about '1,4-Dioxane' provide on 'Explosion hazard'? | Like some other ethers, dioxane combines with atmospheric oxygen upon prolonged exposure to air to form potentially explosive peroxides. Distillation of these mixtures is dangerous. Storage under metallic sodium could limit the risk of explosion. | [
"1,4-Dioxane — Safety\n\nDioxane has an of 5170 mg/kg in rats. It is irritating to the eyes and respiratory tract. Exposure may cause damage to the central nervous system, liver and kidneys. In a 1978 mortality study conducted on workers exposed to 1,4-dioxane, the observed number deaths from cancer was not signifi... |
1,4-Dioxane_14570160 | From the article on '1,4-Dioxane', restate the 'Synthesis' content. | Dioxane is produced by the acid-catalysed dehydration of diethylene glycol, which in turn is obtained from the hydrolysis of ethylene oxide. In 1985, the global production capacity for dioxane was between 11,000 and 14,000 tons. In 1990, the total U.S. production volume of dioxane was between 5,250 and 9,150 tons. | [
"1,4-Dioxane — Safety\n\nDioxane has an of 5170 mg/kg in rats. It is irritating to the eyes and respiratory tract. Exposure may cause damage to the central nervous system, liver and kidneys. In a 1978 mortality study conducted on workers exposed to 1,4-dioxane, the observed number deaths from cancer was not signifi... |
1,4-Dioxane_14570170 | Reconstruct the content about 'Cosmetics' from the article on '1,4-Dioxane'. | have conducted tests on cosmetic raw materials and finished products for the levels of 1,4-dioxane. 1,4-Dioxane was present in ethoxylated raw ingredients at levels up to 1410 ppm (~0.14%wt), and at levels up to 279 ppm (~0.03%wt) in off the shelf cosmetic products. Levels of 1,4-dioxane exceeding 85 ppm (~0.01%wt) in ... | [
"1,4-Dioxane — Safety\n\nDioxane has an of 5170 mg/kg in rats. It is irritating to the eyes and respiratory tract. Exposure may cause damage to the central nervous system, liver and kidneys. In a 1978 mortality study conducted on workers exposed to 1,4-dioxane, the observed number deaths from cancer was not signifi... |
1,4-Dioxane_14570166 | Explain what '1,4-Dioxane' covers in the 'Safety' section. | cubic meter) at concentrations significantly higher than those found in commercial products. Under California Proposition 65, dioxane is classified in the U.S. State of California to cause cancer. Animal studies in rats suggest that the greatest health risk is associated with inhalation of vapors in the pure form. The ... | [
"1,4-Dioxane — Safety\n\nDioxane has an of 5170 mg/kg in rats. It is irritating to the eyes and respiratory tract. Exposure may cause damage to the central nervous system, liver and kidneys. In a 1978 mortality study conducted on workers exposed to 1,4-dioxane, the observed number deaths from cancer was not signifi... |
1,4-Dioxane_14570163 | Explain what '1,4-Dioxane' covers in the 'As a solvent' section. | 2 CH3MgBr + (C2H4O)2 → MgBr2(C2H4O)2 + (CH3)2Mg Dioxane is used in a variety of applications as a versatile aprotic solvent, e. g. for inks, adhesives, and cellulose esters. It is substituted for tetrahydrofuran (THF) in some processes, because of its lower toxicity and higher boiling point (101 °C, versus 66 °C for TH... | [
"1,4-Dioxane — Safety\n\nDioxane has an of 5170 mg/kg in rats. It is irritating to the eyes and respiratory tract. Exposure may cause damage to the central nervous system, liver and kidneys. In a 1978 mortality study conducted on workers exposed to 1,4-dioxane, the observed number deaths from cancer was not signifi... |
1,4-Dioxane_14570168 | Based on the article about '1,4-Dioxane', describe the 'Environment' section. | Dioxane has affected groundwater supplies in several areas. Dioxane at the level of 1 μg/L (~1 ppb) has been detected in many locations in the US. In the U.S. state of New Hampshire, it had been found at 67 sites in 2010, ranging in concentration from 2 ppb to over 11,000 ppb. Thirty of these sites are solid waste land... | [
"1,4-Dioxane — Safety\n\nDioxane has an of 5170 mg/kg in rats. It is irritating to the eyes and respiratory tract. Exposure may cause damage to the central nervous system, liver and kidneys. In a 1978 mortality study conducted on workers exposed to 1,4-dioxane, the observed number deaths from cancer was not signifi... |
1,4-Dioxane_14570159 | Describe the content of the article about '1,4-Dioxane'. | 1,4-Dioxane is a heterocyclic organic compound, classified as an ether. It is a colorless liquid with a faint sweet odor similar to that of diethyl ether. The compound is often called simply dioxane because the other dioxane isomers (1,2- and 1,3-) are rarely encountered. Dioxane is used as a solvent for a variety of p... | [
"1,4-Dioxane — Safety\n\nDioxane has an of 5170 mg/kg in rats. It is irritating to the eyes and respiratory tract. Exposure may cause damage to the central nervous system, liver and kidneys. In a 1978 mortality study conducted on workers exposed to 1,4-dioxane, the observed number deaths from cancer was not signifi... |
1,4-Dioxane_14570161 | What does the article about '1,4-Dioxane' say regarding 'Structure'? | The dioxane molecule is centrosymmetric, meaning that it adopts a chair conformation, typical of relatives of cyclohexane. However, the molecule is conformationally flexible, and the boat conformation is easily adopted, e.g. in the chelation of metal cations. Dioxane resembles a smaller crown ether with only two ethyle... | [
"1,4-Dioxane — Safety\n\nDioxane has an of 5170 mg/kg in rats. It is irritating to the eyes and respiratory tract. Exposure may cause damage to the central nervous system, liver and kidneys. In a 1978 mortality study conducted on workers exposed to 1,4-dioxane, the observed number deaths from cancer was not signifi... |
1,4-Dioxin_18065440 | Describe the 'Polychlorinated dibenzodioxins' section of the article about '1,4-Dioxin'. | Because of their extreme importance as environmental pollutants, current scientific literature uses the name dioxins commonly for simplification to denote the chlorinated derivatives of dibenzo-1,4-dioxin, more precisely the polychlorinated dibenzodioxins (PCDDs), among which 2,3,7,8-tetrachlorodibenzodioxin (TCDD), a ... | [
"1,4-Dioxin — Polychlorinated dibenzodioxins\n\nBecause of their extreme importance as environmental pollutants, current scientific literature uses the name dioxins commonly for simplification to denote the chlorinated derivatives of dibenzo-1,4-dioxin, more precisely the polychlorinated dibenzodioxins (PCDDs), amo... |
1,4-Dioxin_18065437 | Summarize the following section from the article on '1,4-Dioxin'. | 1,4-Dioxin (also referred as dioxin or p-dioxin) is a heterocyclic, organic, non-aromatic compound with the chemical formula C4H4O2. There is an isomeric form of 1,4-dioxin, 1,2-dioxin (or o-dioxin). 1,2-Dioxin is very unstable due to its peroxide-like characteristics. The term “dioxin” is most commonly used for a fami... | [
"1,4-Dioxin — Polychlorinated dibenzodioxins\n\nBecause of their extreme importance as environmental pollutants, current scientific literature uses the name dioxins commonly for simplification to denote the chlorinated derivatives of dibenzo-1,4-dioxin, more precisely the polychlorinated dibenzodioxins (PCDDs), amo... |
1,4-Dioxin_18065439 | Summarize the 'Derivatives' part of '1,4-Dioxin'. | The word “dioxin” can refer in a general way to compounds which have a dioxin core skeletal structure with substituent molecular groups attached to it. For example, dibenzo-1,4-dioxin is a compound whose structure consists of two benzo- groups fused onto a 1,4-dioxin ring. | [
"1,4-Dioxin — Polychlorinated dibenzodioxins\n\nBecause of their extreme importance as environmental pollutants, current scientific literature uses the name dioxins commonly for simplification to denote the chlorinated derivatives of dibenzo-1,4-dioxin, more precisely the polychlorinated dibenzodioxins (PCDDs), amo... |
1,4-Dioxin_18065438 | Based on the article about '1,4-Dioxin', describe the 'Preparation' section. | 1,4-Dioxin can be prepared by cycloaddition, namely by the Diels–Alder reaction of furan and maleic anhydride. The adduct formed has a carbon-carbon double bond, which is converted to an epoxide. The epoxide then undergoes a retro-Diels–Alder reaction, forming 1,4-dioxin and regenerating maleic anhydride. | [
"1,4-Dioxin — Polychlorinated dibenzodioxins\n\nBecause of their extreme importance as environmental pollutants, current scientific literature uses the name dioxins commonly for simplification to denote the chlorinated derivatives of dibenzo-1,4-dioxin, more precisely the polychlorinated dibenzodioxins (PCDDs), amo... |
1,4-Naphthoquinone_13443270 | Describe the 'Reactions' section of the article about '1,4-Naphthoquinone'. | 1,4-Naphthoquinone acts as strong dienophile in Diels-Alder reaction. Its adduct with 1,3-butadiene can be prepared by two methods: 1) long (45 days) exposure of naphthoquinone in neat liquid butadiene taken in huge excess at room temperature in a thick-wall glass tube or 2) fast catalyzed cycloaddition at low temperat... | [
"1,4-Naphthoquinone — Reactions\n\n1,4-Naphthoquinone acts as strong dienophile in Diels-Alder reaction. Its adduct with 1,3-butadiene can be prepared by two methods: 1) long (45 days) exposure of naphthoquinone in neat liquid butadiene taken in huge excess at room temperature in a thick-wall glass tube or 2) fast ... |
1,4-Naphthoquinone_13443268 | Summarize the following section from the article on '1,4-Naphthoquinone'. | 1,4-Naphthoquinone or para-naphthoquinone is an quinone derived from naphthalene. It forms volatile yellow triclinic crystals and has a sharp odor similar to benzoquinone. It is almost insoluble in cold water, slightly soluble in petroleum ether, and more soluble in polar organic solvents. In alkaline solutions it prod... | [
"1,4-Naphthoquinone — Reactions\n\n1,4-Naphthoquinone acts as strong dienophile in Diels-Alder reaction. Its adduct with 1,3-butadiene can be prepared by two methods: 1) long (45 days) exposure of naphthoquinone in neat liquid butadiene taken in huge excess at room temperature in a thick-wall glass tube or 2) fast ... |
1,4-Naphthoquinone_13443272 | Describe the 'Derivatives' section of the article about '1,4-Naphthoquinone'. | Naphthoquinone forms the central chemical structure of many natural compounds, most notably the K vitamins. 2-Methyl-1,4-naphthoquinone, called menadione, is a more effective coagulant than vitamin K. Other natural naphtoquinones include juglone, plumbagin, droserone. Naphthoquinone derivatives have significant pharmac... | [
"1,4-Naphthoquinone — Reactions\n\n1,4-Naphthoquinone acts as strong dienophile in Diels-Alder reaction. Its adduct with 1,3-butadiene can be prepared by two methods: 1) long (45 days) exposure of naphthoquinone in neat liquid butadiene taken in huge excess at room temperature in a thick-wall glass tube or 2) fast ... |
1,4-Naphthoquinone_13443269 | Explain what '1,4-Naphthoquinone' covers in the 'Preparation' section. | C10H8 + 3/2 O2 → C10H6O2 + H2O The industrial synthesis involves aerobic oxidation of naphthalene over a vanadium oxide catalyst: In the laboratory, naphthoquinone can be produced by the oxidation of a variety of naphthalene compounds. An inexpensive route involves oxidation of naphthalene with chromium trioxide... | [
"1,4-Naphthoquinone — Reactions\n\n1,4-Naphthoquinone acts as strong dienophile in Diels-Alder reaction. Its adduct with 1,3-butadiene can be prepared by two methods: 1) long (45 days) exposure of naphthoquinone in neat liquid butadiene taken in huge excess at room temperature in a thick-wall glass tube or 2) fast ... |
1,4-dihydroxy-2-naphthoate_polyprenyltransferase_10711030 | Based on the article about '1,4-dihydroxy-2-naphthoate polyprenyltransferase', describe the 'Inhibitors and activators' section. | Both E. coli and Micrococcus luterus require Mg2+ to work and a pH of 7 in Micrococcus luterus is optimal. EDTA is also an activating compound for the enzyme in Micrococcus luterus at an optimal concentration of 5mM but once it reaches 20mM it becomes an inhibitor and Mg2+is required to reactivate it. | [
"1,4-dihydroxy-2-naphthoate polyprenyltransferase — Inhibitors and activators\n\nBoth E. coli and Micrococcus luterus require Mg2+ to work and a pH of 7 in Micrococcus luterus is optimal. EDTA is also an activating compound for the enzyme in Micrococcus luterus at an optimal concentration of 5mM but once it reaches... |
1,4-dihydroxy-2-naphthoate_polyprenyltransferase_10711029 | Based on the article about '1,4-dihydroxy-2-naphthoate polyprenyltransferase', describe the 'Function' section. | 1-4-dihydroxy-2-napthoate polyprenyltransferase is the 8th out of 9 steps in the biosynthesis of menaquinone (Vitamin K), specifically -9 within ecoli. Vitamin K is a cofactor vital for living and functions as one electron transporter in photosynthesis as a redox molecule. The reactions this enzyme catalyzes works by t... | [
"1,4-dihydroxy-2-naphthoate polyprenyltransferase — Inhibitors and activators\n\nBoth E. coli and Micrococcus luterus require Mg2+ to work and a pH of 7 in Micrococcus luterus is optimal. EDTA is also an activating compound for the enzyme in Micrococcus luterus at an optimal concentration of 5mM but once it reaches... |
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