Full metadata record
DC Field | Value | Language |
---|---|---|
dc.contributor.author | 엄익환 | - |
dc.date.accessioned | 2016-08-27T04:08:54Z | - |
dc.date.available | 2016-08-27T04:08:54Z | - |
dc.date.issued | 2014 | - |
dc.identifier.issn | 0253-2964 | - |
dc.identifier.issn | 1229-5949 | - |
dc.identifier.other | OAK-11671 | - |
dc.identifier.uri | https://dspace.ewha.ac.kr/handle/2015.oak/216871 | - |
dc.description.abstract | A kinetic study is reported for the SNAr reaction of 1-Y-substituted-phenoxy-2,4-dinitrobenzenes (1a-1h) with OH- in 80 mol % H2O/20 mol % DMSO at 25.0 +/- 0.1 degrees C. The second-order rate constant (k(OH)-) increases as the substituent Y in the leaving group changes from an electron-donating group (EDG) to an electron-withdrawing group (EWG). The Bronsted-type plot for the reactions of 1a-1h is linear with beta(lg) = -0.16, indicating that the reactivity of substrates 1a-1h is little affected by the leaving-group basicity. A linear Bronsted-type plot with beta(lg) = -0.3 +/- 0.1 is typical for reactions reported previously to proceed through a stepwise mechanism in which formation of a Meisenheimer complex is the rate-determining step (RDS). The Hammett plot correlated with ay constants results in a much better correlation than that correlated with cry constants, implyng that no negative charge is developing on the O atom of the leaving group (or expulsion of the leaving group is not advanced at all in the TS). This excludes a possibility that the SNAr reaction of 1a-1h with OH- proceeds through a concerted mechanism or via a stepwise pathway with expulsion of the leaving group being the RDS. Thus, the current reactions have been concluded to proceed through a stepwise mechanism in which expulsion of the leaving group occurs rapidly after the RDS. | - |
dc.language | English | - |
dc.publisher | KOREAN CHEMICAL SOC | - |
dc.subject | SNAr reaction | - |
dc.subject | 1-Phenoxy-2,4-dinitrobenzene | - |
dc.subject | Bronsted-type plot | - |
dc.subject | Hammett plot | - |
dc.subject | Reaction mechanism | - |
dc.title | Kinetic Study on SNAr Reaction of 1-Y-Substituted-phenoxy-2,4-dinitrobenzenes with Hydroxide Ion: Effect of Substituent Y on Reactivity and Reaction Mechanism | - |
dc.type | Article | - |
dc.relation.issue | 7 | - |
dc.relation.volume | 35 | - |
dc.relation.index | SCI | - |
dc.relation.index | SCIE | - |
dc.relation.index | SCOPUS | - |
dc.relation.index | KCI | - |
dc.relation.startpage | 2135 | - |
dc.relation.lastpage | 2138 | - |
dc.relation.journaltitle | BULLETIN OF THE KOREAN CHEMICAL SOCIETY | - |
dc.identifier.doi | 10.5012/bkcs.2014.35.7.2135 | - |
dc.identifier.wosid | WOS:000339642700039 | - |
dc.author.google | Kang, Tae-Ah | - |
dc.author.google | Cho, Hyo-Jin | - |
dc.author.google | Um, Ik-Hwan | - |
dc.contributor.scopusid | 엄익환(7006725706;6506759437) | - |
dc.date.modifydate | 20230411105538 | - |