Molecular complexes and solvation interactions in the reaction of quinone imines with thiols
This study aims to investigate the role of complexation between reagents and the role of solvation of reagents by solvents in the kinetics of chain reactions of quinone imines with thiols. The thermodynamic characteristics of the complexation of quinone imines with thiophenol in CCl 4 , chlorobenzen...
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| Veröffentlicht in: | Russian chemical bulletin 2018-10, Vol.67 (10), p.1851-1856 |
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| container_title | Russian chemical bulletin |
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| creator | Varlamov, V. T. Krisyuk, B. E. Grigorev, V. Yu |
| description | This study aims to investigate the role of complexation between reagents and the role of solvation of reagents by solvents in the kinetics of chain reactions of quinone imines with thiols. The thermodynamic characteristics of the complexation of quinone imines with thiophenol in CCl
4
, chlorobenzene, and ethanol, as well as of the complexation of quinone imines and thiophenol with these solvents were calculated by quantum chemical methods (DFT calculations at the PBE/cc-pVDZ level of theory) and in terms of the additive-multiplicative model. Both approaches give consistent results. The formation of molecular complexes in quinone imine–thiphenol systems is accompanied by a 10–30 kJ mol
–1
decrease in enthalpy and has only a slight effect on the reaction mechanism. |
| doi_str_mv | 10.1007/s11172-018-2298-x |
| format | Article |
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4
, chlorobenzene, and ethanol, as well as of the complexation of quinone imines and thiophenol with these solvents were calculated by quantum chemical methods (DFT calculations at the PBE/cc-pVDZ level of theory) and in terms of the additive-multiplicative model. Both approaches give consistent results. The formation of molecular complexes in quinone imine–thiphenol systems is accompanied by a 10–30 kJ mol
–1
decrease in enthalpy and has only a slight effect on the reaction mechanism.</description><identifier>ISSN: 1066-5285</identifier><identifier>EISSN: 1573-9171</identifier><identifier>DOI: 10.1007/s11172-018-2298-x</identifier><language>eng</language><publisher>New York: Springer US</publisher><subject>ADDITIVES ; BENZOQUINONES ; CARBON TETRACHLORIDE ; CHAIN REACTIONS ; Chemistry ; Chemistry and Materials Science ; Chemistry/Food Science ; Chlorobenzene ; Complexation ; ENTHALPY ; ETHANOL ; IMINES ; Inorganic Chemistry ; INORGANIC, ORGANIC, PHYSICAL AND ANALYTICAL CHEMISTRY ; INTERACTIONS ; Organic Chemistry ; Quantum chemistry ; REACTION KINETICS ; Reaction mechanisms ; REAGENTS ; SOLVATION ; SOLVENTS ; THERMODYNAMICS ; THIOLS ; Thiophenol ; THIOPHENOLS</subject><ispartof>Russian chemical bulletin, 2018-10, Vol.67 (10), p.1851-1856</ispartof><rights>Springer Science+Business Media, LLC, part of Springer Nature 2018</rights><rights>Copyright Springer Science & Business Media 2018</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c344t-9483014184c7c25ffeec014278d0e27d995c475519cdb14c6559e1f77703f9733</citedby><cites>FETCH-LOGICAL-c344t-9483014184c7c25ffeec014278d0e27d995c475519cdb14c6559e1f77703f9733</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://link.springer.com/content/pdf/10.1007/s11172-018-2298-x$$EPDF$$P50$$Gspringer$$H</linktopdf><linktohtml>$$Uhttps://link.springer.com/10.1007/s11172-018-2298-x$$EHTML$$P50$$Gspringer$$H</linktohtml><link.rule.ids>230,314,780,784,885,27924,27925,41488,42557,51319</link.rule.ids><backlink>$$Uhttps://www.osti.gov/biblio/22943439$$D View this record in Osti.gov$$Hfree_for_read</backlink></links><search><creatorcontrib>Varlamov, V. T.</creatorcontrib><creatorcontrib>Krisyuk, B. E.</creatorcontrib><creatorcontrib>Grigorev, V. Yu</creatorcontrib><title>Molecular complexes and solvation interactions in the reaction of quinone imines with thiols</title><title>Russian chemical bulletin</title><addtitle>Russ Chem Bull</addtitle><description>This study aims to investigate the role of complexation between reagents and the role of solvation of reagents by solvents in the kinetics of chain reactions of quinone imines with thiols. The thermodynamic characteristics of the complexation of quinone imines with thiophenol in CCl
4
, chlorobenzene, and ethanol, as well as of the complexation of quinone imines and thiophenol with these solvents were calculated by quantum chemical methods (DFT calculations at the PBE/cc-pVDZ level of theory) and in terms of the additive-multiplicative model. Both approaches give consistent results. The formation of molecular complexes in quinone imine–thiphenol systems is accompanied by a 10–30 kJ mol
–1
decrease in enthalpy and has only a slight effect on the reaction mechanism.</description><subject>ADDITIVES</subject><subject>BENZOQUINONES</subject><subject>CARBON TETRACHLORIDE</subject><subject>CHAIN REACTIONS</subject><subject>Chemistry</subject><subject>Chemistry and Materials Science</subject><subject>Chemistry/Food Science</subject><subject>Chlorobenzene</subject><subject>Complexation</subject><subject>ENTHALPY</subject><subject>ETHANOL</subject><subject>IMINES</subject><subject>Inorganic Chemistry</subject><subject>INORGANIC, ORGANIC, PHYSICAL AND ANALYTICAL CHEMISTRY</subject><subject>INTERACTIONS</subject><subject>Organic Chemistry</subject><subject>Quantum chemistry</subject><subject>REACTION KINETICS</subject><subject>Reaction mechanisms</subject><subject>REAGENTS</subject><subject>SOLVATION</subject><subject>SOLVENTS</subject><subject>THERMODYNAMICS</subject><subject>THIOLS</subject><subject>Thiophenol</subject><subject>THIOPHENOLS</subject><issn>1066-5285</issn><issn>1573-9171</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2018</creationdate><recordtype>article</recordtype><recordid>eNp1kE9LAzEQxRdRsFY_gLeA59VMNmmSoxT_QcWL3oSwprM2ZZu0Sar125uyQk-e5s3we4_hVdUl0GugVN4kAJCspqBqxrSqd0fVCIRsag0Sjoumk0ktmBKn1VlKS0opU0qNqvfn0KPd9m0kNqzWPe4wkdbPSQr9V5td8MT5jLG1e53KQvICScThQEJHNlvng0fiVs4X87fLi8K40Kfz6qRr-4QXf3Ncvd3fvU4f69nLw9P0dlbbhvNca64aChwUt9Iy0XWItuxMqjlFJudaC8ulEKDt_AO4nQihETopJW06LZtmXF0NuSFlZ5J1Ge3CBu_RZlPq4A1v9IFax7DZYspmGbbRl8cMA06FnghghYKBsjGkFLEz6-hWbfwxQM2-ajNUbUrV-2xldsXDBk8qrP_EeEj-3_QLlOiBSw</recordid><startdate>20181001</startdate><enddate>20181001</enddate><creator>Varlamov, V. T.</creator><creator>Krisyuk, B. E.</creator><creator>Grigorev, V. Yu</creator><general>Springer US</general><general>Springer Nature B.V</general><scope>AAYXX</scope><scope>CITATION</scope><scope>OTOTI</scope></search><sort><creationdate>20181001</creationdate><title>Molecular complexes and solvation interactions in the reaction of quinone imines with thiols</title><author>Varlamov, V. T. ; Krisyuk, B. E. ; Grigorev, V. Yu</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c344t-9483014184c7c25ffeec014278d0e27d995c475519cdb14c6559e1f77703f9733</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2018</creationdate><topic>ADDITIVES</topic><topic>BENZOQUINONES</topic><topic>CARBON TETRACHLORIDE</topic><topic>CHAIN REACTIONS</topic><topic>Chemistry</topic><topic>Chemistry and Materials Science</topic><topic>Chemistry/Food Science</topic><topic>Chlorobenzene</topic><topic>Complexation</topic><topic>ENTHALPY</topic><topic>ETHANOL</topic><topic>IMINES</topic><topic>Inorganic Chemistry</topic><topic>INORGANIC, ORGANIC, PHYSICAL AND ANALYTICAL CHEMISTRY</topic><topic>INTERACTIONS</topic><topic>Organic Chemistry</topic><topic>Quantum chemistry</topic><topic>REACTION KINETICS</topic><topic>Reaction mechanisms</topic><topic>REAGENTS</topic><topic>SOLVATION</topic><topic>SOLVENTS</topic><topic>THERMODYNAMICS</topic><topic>THIOLS</topic><topic>Thiophenol</topic><topic>THIOPHENOLS</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Varlamov, V. T.</creatorcontrib><creatorcontrib>Krisyuk, B. E.</creatorcontrib><creatorcontrib>Grigorev, V. Yu</creatorcontrib><collection>CrossRef</collection><collection>OSTI.GOV</collection><jtitle>Russian chemical bulletin</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Varlamov, V. T.</au><au>Krisyuk, B. E.</au><au>Grigorev, V. Yu</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Molecular complexes and solvation interactions in the reaction of quinone imines with thiols</atitle><jtitle>Russian chemical bulletin</jtitle><stitle>Russ Chem Bull</stitle><date>2018-10-01</date><risdate>2018</risdate><volume>67</volume><issue>10</issue><spage>1851</spage><epage>1856</epage><pages>1851-1856</pages><issn>1066-5285</issn><eissn>1573-9171</eissn><abstract>This study aims to investigate the role of complexation between reagents and the role of solvation of reagents by solvents in the kinetics of chain reactions of quinone imines with thiols. The thermodynamic characteristics of the complexation of quinone imines with thiophenol in CCl
4
, chlorobenzene, and ethanol, as well as of the complexation of quinone imines and thiophenol with these solvents were calculated by quantum chemical methods (DFT calculations at the PBE/cc-pVDZ level of theory) and in terms of the additive-multiplicative model. Both approaches give consistent results. The formation of molecular complexes in quinone imine–thiphenol systems is accompanied by a 10–30 kJ mol
–1
decrease in enthalpy and has only a slight effect on the reaction mechanism.</abstract><cop>New York</cop><pub>Springer US</pub><doi>10.1007/s11172-018-2298-x</doi><tpages>6</tpages></addata></record> |
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| subjects | ADDITIVES BENZOQUINONES CARBON TETRACHLORIDE CHAIN REACTIONS Chemistry Chemistry and Materials Science Chemistry/Food Science Chlorobenzene Complexation ENTHALPY ETHANOL IMINES Inorganic Chemistry INORGANIC, ORGANIC, PHYSICAL AND ANALYTICAL CHEMISTRY INTERACTIONS Organic Chemistry Quantum chemistry REACTION KINETICS Reaction mechanisms REAGENTS SOLVATION SOLVENTS THERMODYNAMICS THIOLS Thiophenol THIOPHENOLS |
| title | Molecular complexes and solvation interactions in the reaction of quinone imines with thiols |
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