Full metadata record
DC Field | Value | Language |
---|---|---|
dc.contributor.author | 엄익환 | - |
dc.date.accessioned | 2016-08-28T12:08:40Z | - |
dc.date.available | 2016-08-28T12:08:40Z | - |
dc.date.issued | 2007 | - |
dc.identifier.issn | 0253-2964 | - |
dc.identifier.other | OAK-3892 | - |
dc.identifier.uri | https://dspace.ewha.ac.kr/handle/2015.oak/219839 | - |
dc.description.abstract | Second-order rate constants (kN) have been determined spectrophotometrically for reactions of 2,4-dintrophenyl 2-furoate (2) with a series of alicyclic secondary amines in 80 mol % H2O/20 mol % dimethyl sulfoxide (DMSO) at 25.0°C. The furoate 2 is more reactive than 2,4-dintrophenyl benzoate (1) toward all the amines studied. The higher acidity of 2-furoic acid (pKa = 3.16) compared with benzoic acid (pK a = 4.20) has been suggested to be responsible for the reactivity order, at least in part. The Brønsted-type plots for the reactions of 1 and 2 are curved downwardly, indicating that the aminolyses of both 1 and 2 proceed through a zwitterionic tetrahedral intermediate (T±) with a change in the rate-determining step on changing the amine basicity. Dissection of the kN values into their microscopic rate constants has revealed that the pKa° and k2/k-1 ratios for the reactions of 1 and 2 are identical, indicating that the nature of the nonleaving group (i.e., benzoyl and 2-furoyl) does not affect the reaction mechanism. The k1 values have been found to be larger for the reactions of 2 than for those of 1, which is fully responsible for the fact that the former is more reactive than the latter. | - |
dc.language | English | - |
dc.title | Aminolyses of 2,4-dinitrophenyl 2-furoate and benzoate: Effect of nonleaving group on reactivity and mechanism | - |
dc.type | Article | - |
dc.relation.issue | 2 | - |
dc.relation.volume | 28 | - |
dc.relation.index | SCI | - |
dc.relation.index | SCIE | - |
dc.relation.index | SCOPUS | - |
dc.relation.index | KCI | - |
dc.relation.startpage | 220 | - |
dc.relation.lastpage | 224 | - |
dc.relation.journaltitle | Bulletin of the Korean Chemical Society | - |
dc.identifier.wosid | WOS:000245197800013 | - |
dc.identifier.scopusid | 2-s2.0-33847234272 | - |
dc.author.google | Um I.-H. | - |
dc.author.google | Chun S.-M. | - |
dc.author.google | Akhtar K. | - |
dc.contributor.scopusid | 엄익환(7006725706;6506759437) | - |
dc.date.modifydate | 20230411105538 | - |