Full metadata record
DC Field | Value | Language |
---|---|---|
dc.contributor.author | 엄익환 | - |
dc.contributor.author | 한소엽 | - |
dc.date.accessioned | 2016-08-29T12:08:18Z | - |
dc.date.available | 2016-08-29T12:08:18Z | - |
dc.date.issued | 2015 | - |
dc.identifier.issn | 0253-2964 | - |
dc.identifier.other | OAK-15257 | - |
dc.identifier.uri | https://dspace.ewha.ac.kr/handle/2015.oak/230686 | - |
dc.description.abstract | Second-order rate constants (k<inf>N3-</inf>) for S<inf>N</inf>Ar reactions of 1-(Y-substituted-phenoxy)-2,4-dinitrobenzenes (2a-2h) with (Formula presented.) in 80 mol % H<inf>2</inf>O/20 mol % DMSO at 25.0 ± 0.1 °C have been measured spectrophotometrically. The Brønsted-type plot is linear with β<inf>1g</inf>=-0.38. The Hammett plots correlated with (Formula presented.) constants exhibit highly scattered points. In contrast, the Yukawa-Tsuno plot results in an excellent linear correlation with <inf>ρY</inf> = 1.02 and r = 0.51, indicating that a negative charge develops partially on the O atom of the leaving Y-substituted-phenoxy moiety in the transition state. Accordingly, the reactions have been concluded to proceed through a stepwise mechanism, in which expulsion of the leaving group occurs in the rate-determining step. Comparison of k<inf>N3-</inf> with the k<inf>OH-</inf> values reported previously for the corresponding reactions with OH¯ has revealed that (Formula presented.) is only 6- to 26-fold than OH¯ toward substrates 2a-2h, although the former is over 11 pK<inf>a</inf> units less basic than the latter. Solvation and polarizability effects have been suggested to be responsible for the unusual reactivity shown by (Formula presented.) and OH¯. Effects of changing nucleophile from OH¯ to (Formula presented) on reaction mechanism and reactivity are discussed in detail. © 2015 Korean Chemical Society, Seoul & Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim. | - |
dc.language | English | - |
dc.publisher | Korean Chemical Society | - |
dc.subject | 1-Phenoxy-2, 4-dinitrobenzene | - |
dc.subject | Hammett plot | - |
dc.subject | Rate-determining step | - |
dc.subject | S<inf>N</inf>Ar reaction | - |
dc.subject | Yukawa-Tsuno plot | - |
dc.title | Kinetic study on S<inf>N</inf>Ar reactions of 1-(Y-substituted-phenoxy)-2,4-dinitrobenzenes with Azide ion: Effect of changing nucleophile from hydroxide to Azide ion on reaction mechanism and reactivity | - |
dc.type | Article | - |
dc.relation.issue | 7 | - |
dc.relation.volume | 36 | - |
dc.relation.index | SCI | - |
dc.relation.index | SCIE | - |
dc.relation.index | SCOPUS | - |
dc.relation.index | KCI | - |
dc.relation.startpage | 1764 | - |
dc.relation.lastpage | 1768 | - |
dc.relation.journaltitle | Bulletin of the Korean Chemical Society | - |
dc.identifier.doi | 10.1002/bkcs.10333 | - |
dc.identifier.wosid | WOS:000357430700008 | - |
dc.identifier.scopusid | 2-s2.0-84936803951 | - |
dc.author.google | Seo H.-O. | - |
dc.author.google | Kim M.-Y. | - |
dc.author.google | Han S.-Y. | - |
dc.author.google | Um I.-H. | - |
dc.contributor.scopusid | 엄익환(7006725706;6506759437) | - |
dc.contributor.scopusid | 한소엽(7405944194) | - |
dc.date.modifydate | 20230411105538 | - |