Full metadata record
DC Field | Value | Language |
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dc.contributor.author | 엄익환 | - |
dc.date.accessioned | 2017-02-15T08:02:24Z | - |
dc.date.available | 2017-02-15T08:02:24Z | - |
dc.date.issued | 2007 | - |
dc.identifier.issn | 0022-3263 | - |
dc.identifier.other | OAK-4065 | - |
dc.identifier.uri | https://dspace.ewha.ac.kr/handle/2015.oak/234364 | - |
dc.description.abstract | (Chemical Equation Presented) A kinetic study is reported for reactions of Y-substituted phenyl X-substituted cinnamates (1a-e and 3a-g) and benzoates (2a-e and 4a-g) with a series of alicyclic secondary amines in 80 mol % H 2O/20 mol % DMSO at 25.0 ± 0.1°C. Reactions of 2,4-dinitrophenyl X-substituted cinnamates (1a-e) and benzoates (2a-e) with amines result in linear Yukawa-Tsuno plots. The ρX values are much smaller for the reactions of 1a-e than for those of 2a-e. A distance effect and the nature of the reaction mechanism (i.e., a concerted mechanism for 1a-e) have been suggested to be responsible for the small ρX values. The Brønsted-type plots for the reactions of 2,4-dinitrophenyl X-substituted cinnamates (1a, 1c, and 1e) with amines are curved with a decreasing βnuc value from 0.65 to 0.3-0.4. The reactions of Y-substituted phenyl cinnamates (3a-g) with morpholine also result in a curved Brønsted plot, while the corresponding reactions of Y-substituted phenyl benzoates (4a-e) exhibit a linear Brønsted plot. It has been concluded that the curved Brønsted plots found for the reactions of the cinnamates (1a, 1c, 1e, and 3a-g) are not due to a change in the rate-determining step (RDS) but due to a normal Hammond effect for a concerted mechanism, that is, an earlier transition state (TS) for a more reactive amine or substrate. © 2007 American Chemical Society. | - |
dc.language | English | - |
dc.title | Aminolysis of Y-substituted phenyl X-substituted cinnamates and benzoates: Effect of modification of the nonleaving group from benzoyl to cinnamoyl | - |
dc.type | Article | - |
dc.relation.issue | 13 | - |
dc.relation.volume | 72 | - |
dc.relation.index | SCI | - |
dc.relation.index | SCIE | - |
dc.relation.index | SCOPUS | - |
dc.relation.startpage | 4816 | - |
dc.relation.lastpage | 4821 | - |
dc.relation.journaltitle | Journal of Organic Chemistry | - |
dc.identifier.doi | 10.1021/jo0705061 | - |
dc.identifier.wosid | WOS:000247246100026 | - |
dc.identifier.scopusid | 2-s2.0-34250893184 | - |
dc.author.google | Um I.-H. | - |
dc.author.google | Park Y.-M. | - |
dc.author.google | Fujio M. | - |
dc.author.google | Mishima M. | - |
dc.author.google | Tsuno Y. | - |
dc.contributor.scopusid | 엄익환(7006725706;6506759437) | - |
dc.date.modifydate | 20230411105538 | - |