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dc.contributor.author엄익환-
dc.date.accessioned2016-08-28T12:08:53Z-
dc.date.available2016-08-28T12:08:53Z-
dc.date.issued2011-
dc.identifier.issn0253-2964-
dc.identifier.otherOAK-7729-
dc.identifier.urihttps://dspace.ewha.ac.kr/handle/2015.oak/221743-
dc.description.abstractA kinetic study is reported for nucleophilic substitution reactions of 4-pyridyl X-substituted benzoates 7a-e with a series of alicyclic secondary amines in H 2O. The Brønsted-type plot for the reactions of 4-pyridyl benzoate 7c is linear with β nuc = 0.71. The corresponding reactions of 2-pyridyl benzoate 6, which is less reactive than 7c, resulted in also a linear Brønsted-type plot with β nuc = 0.77. The fact that the more reactive 7c results in a smaller β nuc value appears to be in accord with the reactivity- selectivity principle. The aminolysis of 7c has been suggested to proceed through a stepwise mechanism in which breakdown of the intermediate is the rate-determining step (RDS). The Hammett plot for the reactions of 7a-e with piperidine consists of two intersecting straight lines, i.e., ρ X = 1.47 for substrates possessing an electron-donating group (EDG) and ρ X = 0.91 for those possessing an electron-withdrawing group (EWG). In contrast, the corresponding Yukawa- Tsuno plot exhibits excellent linear correlation with ρ X = 0.79 and r = 0.56. Thus, it has been concluded that the nonlinear Hammett plot is not due to a change in the RDS but is caused by stabilization of the ground state of the substrates possessing an EDG through resonance interaction between the EDG and the C=O bond of the substrates.-
dc.languageEnglish-
dc.titleKinetic study on aminolysis of 4-pyridyl X-substituted benzoates: Effect of substituent X on reactivity and reaction mechanism-
dc.typeArticle-
dc.relation.issue6-
dc.relation.volume32-
dc.relation.indexSCI-
dc.relation.indexSCIE-
dc.relation.indexSCOPUS-
dc.relation.indexKCI-
dc.relation.startpage1907-
dc.relation.lastpage1911-
dc.relation.journaltitleBulletin of the Korean Chemical Society-
dc.identifier.doi10.5012/bkcs.2011.32.6.1907-
dc.identifier.wosidWOS:000292117700013-
dc.identifier.scopusid2-s2.0-79959424801-
dc.author.googleLee J.P.-
dc.author.googleBae A.R.-
dc.author.googleUm I.-H.-
dc.contributor.scopusid엄익환(7006725706;6506759437)-
dc.date.modifydate20230411105538-
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자연과학대학 > 화학·나노과학전공 > Journal papers
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