Arenesulfonylation of N-alkylanilines: reaction kinetics and mechanism
Kinetic regularities of arenesulfonylation of N -alkylanilines in binary water-organic solvents of variable composition have been studied. The rate constants for these reactions increase with increasing the water content in a system. The steric factor has the decisive influence on reactivity of N -a...
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| Veröffentlicht in: | Russian chemical bulletin 2017-06, Vol.66 (6), p.999-1006 |
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| container_title | Russian chemical bulletin |
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| creator | Kochetova, L. B. Kustova, T. P. Kuritsyn, L. V. Katushkin, A. A. |
| description | Kinetic regularities of arenesulfonylation of
N
-alkylanilines in binary water-organic solvents of variable composition have been studied. The rate constants for these reactions increase with increasing the water content in a system. The steric factor has the decisive influence on reactivity of
N
-alkylamines. The character of the influence of the composition and nature of a solvent on the rate constants for arenesulfonylation was discussed with the assistance of results of quantum chemical simulation of molecular complexes of the nucleophiles studied with the components of the binary systems. Calculation of potential energy surface for the reaction of
N
-methylaniline with benzenesulfonyl chloride showed that in the gas phase the process occurs by the S
N
2 mechanism. |
| doi_str_mv | 10.1007/s11172-017-1846-0 |
| format | Article |
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N
-alkylanilines in binary water-organic solvents of variable composition have been studied. The rate constants for these reactions increase with increasing the water content in a system. The steric factor has the decisive influence on reactivity of
N
-alkylamines. The character of the influence of the composition and nature of a solvent on the rate constants for arenesulfonylation was discussed with the assistance of results of quantum chemical simulation of molecular complexes of the nucleophiles studied with the components of the binary systems. Calculation of potential energy surface for the reaction of
N
-methylaniline with benzenesulfonyl chloride showed that in the gas phase the process occurs by the S
N
2 mechanism.</description><identifier>ISSN: 1066-5285</identifier><identifier>EISSN: 1573-9171</identifier><identifier>DOI: 10.1007/s11172-017-1846-0</identifier><language>eng</language><publisher>New York: Springer US</publisher><subject>Alkylamines ; Binary systems ; Chemistry ; Chemistry and Materials Science ; Chemistry/Food Science ; CHLORIDES ; Full Articles ; HUMIDITY ; Inorganic Chemistry ; INORGANIC, ORGANIC, PHYSICAL AND ANALYTICAL CHEMISTRY ; Kinetics ; Moisture content ; Nucleophiles ; Organic Chemistry ; ORGANIC SOLVENTS ; POTENTIAL ENERGY ; Quantum chemistry ; Rate constants ; REACTION KINETICS ; REACTIVITY ; SIMULATION ; WATER</subject><ispartof>Russian chemical bulletin, 2017-06, Vol.66 (6), p.999-1006</ispartof><rights>Springer Science+Business Media, LLC 2017</rights><rights>Copyright Springer Science & Business Media 2017</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c344t-2c2b0b488693f306f3f92797206fac51438e302165dc9098211c0b0e22c9fc303</citedby><cites>FETCH-LOGICAL-c344t-2c2b0b488693f306f3f92797206fac51438e302165dc9098211c0b0e22c9fc303</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/s11172-017-1846-0$$EPDF$$P50$$Gspringer$$H</linktopdf><linktohtml>$$Uhttps://link.springer.com/10.1007/s11172-017-1846-0$$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/22863564$$D View this record in Osti.gov$$Hfree_for_read</backlink></links><search><creatorcontrib>Kochetova, L. B.</creatorcontrib><creatorcontrib>Kustova, T. P.</creatorcontrib><creatorcontrib>Kuritsyn, L. V.</creatorcontrib><creatorcontrib>Katushkin, A. A.</creatorcontrib><title>Arenesulfonylation of N-alkylanilines: reaction kinetics and mechanism</title><title>Russian chemical bulletin</title><addtitle>Russ Chem Bull</addtitle><description>Kinetic regularities of arenesulfonylation of
N
-alkylanilines in binary water-organic solvents of variable composition have been studied. The rate constants for these reactions increase with increasing the water content in a system. The steric factor has the decisive influence on reactivity of
N
-alkylamines. The character of the influence of the composition and nature of a solvent on the rate constants for arenesulfonylation was discussed with the assistance of results of quantum chemical simulation of molecular complexes of the nucleophiles studied with the components of the binary systems. Calculation of potential energy surface for the reaction of
N
-methylaniline with benzenesulfonyl chloride showed that in the gas phase the process occurs by the S
N
2 mechanism.</description><subject>Alkylamines</subject><subject>Binary systems</subject><subject>Chemistry</subject><subject>Chemistry and Materials Science</subject><subject>Chemistry/Food Science</subject><subject>CHLORIDES</subject><subject>Full Articles</subject><subject>HUMIDITY</subject><subject>Inorganic Chemistry</subject><subject>INORGANIC, ORGANIC, PHYSICAL AND ANALYTICAL CHEMISTRY</subject><subject>Kinetics</subject><subject>Moisture content</subject><subject>Nucleophiles</subject><subject>Organic Chemistry</subject><subject>ORGANIC SOLVENTS</subject><subject>POTENTIAL ENERGY</subject><subject>Quantum chemistry</subject><subject>Rate constants</subject><subject>REACTION KINETICS</subject><subject>REACTIVITY</subject><subject>SIMULATION</subject><subject>WATER</subject><issn>1066-5285</issn><issn>1573-9171</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2017</creationdate><recordtype>article</recordtype><recordid>eNp1kD9PwzAQxS0EEqXwAdgiMRvu7MSx2aqKFqQKFpit1LUhbWoXOx367XEJEixM753ud3_0CLlGuEWA-i4hYs0oYE1RloLCCRlhVXOqsMbT7EEIWjFZnZOLlNYAwKSUIzKbROtt2ncu-EPX9G3wRXDFM226Ta5927W5fV9E25jv5ibXfWtS0fhVsbXmIzNpe0nOXNMle_WjY_I2e3idPtLFy_xpOllQw8uyp8ywJSxLKYXijoNw3ClWq5pl25gKSy4tB4aiWhkFSjJEA0uwjBnlDAc-JjfD3pD6VifT9vkDE7y3pteMScErUf5Suxg-9zb1eh320efHNKqKK8Egy5jgQJkYUorW6V1st008aAR9DFUPoeocqj6Gqo_32TCTMuvfbfyz-d-hL8nid90</recordid><startdate>20170601</startdate><enddate>20170601</enddate><creator>Kochetova, L. B.</creator><creator>Kustova, T. P.</creator><creator>Kuritsyn, L. V.</creator><creator>Katushkin, A. A.</creator><general>Springer US</general><general>Springer Nature B.V</general><scope>AAYXX</scope><scope>CITATION</scope><scope>OTOTI</scope></search><sort><creationdate>20170601</creationdate><title>Arenesulfonylation of N-alkylanilines: reaction kinetics and mechanism</title><author>Kochetova, L. B. ; Kustova, T. P. ; Kuritsyn, L. V. ; Katushkin, A. A.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c344t-2c2b0b488693f306f3f92797206fac51438e302165dc9098211c0b0e22c9fc303</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2017</creationdate><topic>Alkylamines</topic><topic>Binary systems</topic><topic>Chemistry</topic><topic>Chemistry and Materials Science</topic><topic>Chemistry/Food Science</topic><topic>CHLORIDES</topic><topic>Full Articles</topic><topic>HUMIDITY</topic><topic>Inorganic Chemistry</topic><topic>INORGANIC, ORGANIC, PHYSICAL AND ANALYTICAL CHEMISTRY</topic><topic>Kinetics</topic><topic>Moisture content</topic><topic>Nucleophiles</topic><topic>Organic Chemistry</topic><topic>ORGANIC SOLVENTS</topic><topic>POTENTIAL ENERGY</topic><topic>Quantum chemistry</topic><topic>Rate constants</topic><topic>REACTION KINETICS</topic><topic>REACTIVITY</topic><topic>SIMULATION</topic><topic>WATER</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Kochetova, L. B.</creatorcontrib><creatorcontrib>Kustova, T. P.</creatorcontrib><creatorcontrib>Kuritsyn, L. V.</creatorcontrib><creatorcontrib>Katushkin, A. A.</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>Kochetova, L. B.</au><au>Kustova, T. P.</au><au>Kuritsyn, L. V.</au><au>Katushkin, A. A.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Arenesulfonylation of N-alkylanilines: reaction kinetics and mechanism</atitle><jtitle>Russian chemical bulletin</jtitle><stitle>Russ Chem Bull</stitle><date>2017-06-01</date><risdate>2017</risdate><volume>66</volume><issue>6</issue><spage>999</spage><epage>1006</epage><pages>999-1006</pages><issn>1066-5285</issn><eissn>1573-9171</eissn><abstract>Kinetic regularities of arenesulfonylation of
N
-alkylanilines in binary water-organic solvents of variable composition have been studied. The rate constants for these reactions increase with increasing the water content in a system. The steric factor has the decisive influence on reactivity of
N
-alkylamines. The character of the influence of the composition and nature of a solvent on the rate constants for arenesulfonylation was discussed with the assistance of results of quantum chemical simulation of molecular complexes of the nucleophiles studied with the components of the binary systems. Calculation of potential energy surface for the reaction of
N
-methylaniline with benzenesulfonyl chloride showed that in the gas phase the process occurs by the S
N
2 mechanism.</abstract><cop>New York</cop><pub>Springer US</pub><doi>10.1007/s11172-017-1846-0</doi><tpages>8</tpages></addata></record> |
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| subjects | Alkylamines Binary systems Chemistry Chemistry and Materials Science Chemistry/Food Science CHLORIDES Full Articles HUMIDITY Inorganic Chemistry INORGANIC, ORGANIC, PHYSICAL AND ANALYTICAL CHEMISTRY Kinetics Moisture content Nucleophiles Organic Chemistry ORGANIC SOLVENTS POTENTIAL ENERGY Quantum chemistry Rate constants REACTION KINETICS REACTIVITY SIMULATION WATER |
| title | Arenesulfonylation of N-alkylanilines: reaction kinetics and mechanism |
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