Abstract
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 ratedetermining 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.
Original language | English |
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Pages (from-to) | 2810-2814 |
Number of pages | 5 |
Journal | Bulletin of the Korean Chemical Society |
Volume | 36 |
Issue number | 12 |
DOIs | |
Publication status | Published - 2015 Dec 1 |
Keywords
- Bronsted and hammett plots
- Concerted and stepwise mechanism
- Nucleophilic substitution
ASJC Scopus subject areas
- Chemistry(all)