Published December 2015
| Version v1
Journal article
Reactions of aryl 5-substituted-2-thiophenecarboxylates promoted by 4-Z-C6H4O −/4-Z-C6H4OH in 20 mol % DMSO(aq) - Efect of nucleophile on acyl-transfer reaction
- 1. Dept. of Chemistry, Pukyong National University, Pusan (Korea, Republic of)
- 2. Dept. of Chemistry, Daejin University, Pocheon (Korea, Republic of)
- 3. Dept. of Chemistry, Korea University, Seoul (Korea, Republic of)
Description
Nucleophilic substitution reactions of 5-XC4H2 (S)C(O)OC6H3 -2-Y-4-NO2 (1) promoted by 4-Z-C6H4O −/4-Z-C6H4OH in 20 mol % dimethyl sulfoxide (DMSO)(aq) have been studied kinetically. The reactions exhibited second-order kinetics with βacyl = −2.52 to −2.83, ρ(x) = 2.81–3.16, βnuc = 0.88–0.04 and βlg = −0.94, respectively. The results have been interpreted with an addition–elimination mechanism in which the nucleophilic attack occurs in the rate-determining step. Comparison with existing data reveals that the rate-determining step changes from the second to the first step by the change in the nucleophile from R2NH/R2NH2 + to 4-Z-C6H4O −/4-Z-C6H4OH
Additional details
Publishing Information
- Journal Title
- Bulletin of the Korean Chemical Society
- Journal Volume
- 36
- Journal Issue
- 12
- Series
- 33 refs, 5 figs, 5 tabs
- Journal Page Range
- p. 2810-2814
- ISSN
- 0253-2964
INIS
- Country of Publication
- Korea, Republic of
- Country of Input or Organization
- Korea, Republic of
- INIS RN
- 49063845
- Subject category
- S37: INORGANIC, ORGANIC, PHYSICAL AND ANALYTICAL CHEMISTRY;
- Descriptors DEI
- CARBOXYLATION; DATA; KINETICS; MATERIAL SUBSTITUTION; SULFOXIDES
- Descriptors DEC
- CHEMICAL REACTIONS; INFORMATION; ORGANIC COMPOUNDS; ORGANIC SULFUR COMPOUNDS