Full metadata record
DC Field | Value | Language |
---|---|---|
dc.contributor.author | 엄익환 | - |
dc.date.accessioned | 2017-01-05T02:01:25Z | - |
dc.date.available | 2017-01-05T02:01:25Z | - |
dc.date.issued | 2002 | - |
dc.identifier.issn | 0022-3263 | - |
dc.identifier.other | OAK-1250 | - |
dc.identifier.uri | https://dspace.ewha.ac.kr/handle/2015.oak/233756 | - |
dc.description.abstract | A kinetic study is reported for the reaction of the anionic nucleophiles OH-, CN-, and N3- with aryl benzoates containing substituents on the benzoyl as well as the aryloxy moiety, in 80 mol % H2O-20 mol % dimethyl sulfoxide at 25.0 °C. Hammett log k vs σ plots for these systems are consistently nonlinear. However, a possible traditional explanation in terms of a mechanism involving a tetrahedral intermediate with curvature resulting from a change in rate-determining step is considered but rejected. The proposed explanation involves ground-state stabilization through resonance interaction between the benzoyl substituent and the electrophilic carbonyl center in the two-stage mechanism. Accordingly, the data are nicely accommodated on the basis of the Yukawa-Tsuno equation, which gives linear plots for all three nuceophiles. Literature reports of the mechanism of acyl transfer processes are reconsidered in this light. | - |
dc.language | English | - |
dc.title | Reinterpretation of curved hammett plots in reaction of nucleophiles with aryl benzoates: Change in rate-determining step or mechanism versus ground-state stabilization | - |
dc.type | Article | - |
dc.relation.issue | 24 | - |
dc.relation.volume | 67 | - |
dc.relation.index | SCI | - |
dc.relation.index | SCIE | - |
dc.relation.index | SCOPUS | - |
dc.relation.startpage | 8475 | - |
dc.relation.lastpage | 8480 | - |
dc.relation.journaltitle | Journal of Organic Chemistry | - |
dc.identifier.doi | 10.1021/jo026339g | - |
dc.identifier.wosid | WOS:000179509400024 | - |
dc.identifier.scopusid | 2-s2.0-0037195670 | - |
dc.author.google | Um I.-H. | - |
dc.author.google | Han H.-J. | - |
dc.author.google | Ahn J.-A. | - |
dc.author.google | Kang S. | - |
dc.author.google | Buncel E. | - |
dc.contributor.scopusid | 엄익환(7006725706;6506759437) | - |
dc.date.modifydate | 20230411105538 | - |