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dc.contributor.author엄익환-
dc.contributor.author한소엽-
dc.date.accessioned2016-08-29T12:08:07Z-
dc.date.available2016-08-29T12:08:07Z-
dc.date.issued2015-
dc.identifier.issn0253-2964-
dc.identifier.otherOAK-14973-
dc.identifier.urihttp://dspace.ewha.ac.kr/handle/2015.oak/230580-
dc.description.abstractThe second-order rate constants for reactions of 2,4-dinitrophenyl X-substituted-benzenesulfonates (4a-4f) and Y-substituted-phenyl-4-nitrobenzenesulfonates (5a-5f) with N<inf>3</inf>- ion have been measured spectrophotometrically. The reactions of 4a-4f proceed through S-O and C-O bond fission pathways competitively. Fraction of the S-O bond fission decreases rapidly as the substituent X in the benzenesulfonyl moiety changes from an electron-withdrawing group to an electron-donating group. The Hammett plots for reactions of 4a-4f are linear with ρ<inf>X</inf>=1.87 and 0.56 for the S-O and C-O bond fission, respectively. The fact that the substituent X is further away from the reaction site of the C-O bond fission than that of the S-O bond fission is one reason for the smaller ρ<inf>X</inf> value. The nature of the reaction mechanism (i.e., a stepwise mechanism in which expulsion of the leaving group occurs after the rate-determining step) is also responsible for the smaller ρ<inf>X</inf> value obtained from the C-O bond fission. The Brønsted-type plot for the reactions of 5a-5f is linear with β<inf>lg</inf>=-0.63, which is typical for reactions reported previously to proceed through a concerted mechanism. Effects of substituents X and Y on regioselectivity and reaction mechanism are discussed in detail. © 2015 Korean Chemical Society, Seoul & Wiley-VCH Verlag GmbH & Co. KGaA.-
dc.languageEnglish-
dc.publisherKorean Chemical Society-
dc.subjectAryl benzenesulfonates-
dc.subjectAzidolysis-
dc.subjectRegioselectivity-
dc.subjectS<inf>N</inf>Ar reaction-
dc.subjectYukawa-Tsuno plot-
dc.titleNucleophilic Substitution Reactions of 2,4-Dinitrophenyl X-Substituted-Benzenesulfonates and Y-Substituted-Phenyl 4-Nitrobenzenesulfonates with Azide Ion: Regioselectivity and Reaction Mechanism-
dc.typeArticle-
dc.relation.issue5-
dc.relation.volume36-
dc.relation.indexSCI-
dc.relation.indexSCIE-
dc.relation.indexSCOPUS-
dc.relation.indexKCI-
dc.relation.startpage1360-
dc.relation.lastpage1365-
dc.relation.journaltitleBulletin of the Korean Chemical Society-
dc.identifier.doi10.1002/bkcs.10259-
dc.identifier.wosidWOS:000354133600011-
dc.identifier.scopusid2-s2.0-84936854358-
dc.author.googleMoon J.-H.-
dc.author.googleKim M.-Y.-
dc.author.googleHan S.-Y.-
dc.author.googleUm I.-H.-
dc.contributor.scopusid엄익환(7006725706;6506759437)-
dc.contributor.scopusid한소엽(7405944194)-
dc.date.modifydate20200928112844-
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자연과학대학 > 화학·나노과학전공 > Journal papers
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