Full metadata record
DC Field | Value | Language |
---|---|---|
dc.contributor.author | 엄익환 | - |
dc.date.accessioned | 2016-08-28T12:08:53Z | - |
dc.date.available | 2016-08-28T12:08:53Z | - |
dc.date.issued | 2011 | - |
dc.identifier.issn | 0253-2964 | - |
dc.identifier.other | OAK-7729 | - |
dc.identifier.uri | https://dspace.ewha.ac.kr/handle/2015.oak/221743 | - |
dc.description.abstract | A 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.language | English | - |
dc.title | Kinetic study on aminolysis of 4-pyridyl X-substituted benzoates: Effect of substituent X on reactivity and reaction mechanism | - |
dc.type | Article | - |
dc.relation.issue | 6 | - |
dc.relation.volume | 32 | - |
dc.relation.index | SCI | - |
dc.relation.index | SCIE | - |
dc.relation.index | SCOPUS | - |
dc.relation.index | KCI | - |
dc.relation.startpage | 1907 | - |
dc.relation.lastpage | 1911 | - |
dc.relation.journaltitle | Bulletin of the Korean Chemical Society | - |
dc.identifier.doi | 10.5012/bkcs.2011.32.6.1907 | - |
dc.identifier.wosid | WOS:000292117700013 | - |
dc.identifier.scopusid | 2-s2.0-79959424801 | - |
dc.author.google | Lee J.P. | - |
dc.author.google | Bae A.R. | - |
dc.author.google | Um I.-H. | - |
dc.contributor.scopusid | 엄익환(7006725706;6506759437) | - |
dc.date.modifydate | 20230411105538 | - |