Reactions of aryl 5-substituted-2-thiophenecarboxylates promoted by 4-Z-C6H4O-/4-Z-C6H4OH in 20 mol % DMSO(aq). Effect of nucleophile on acyl-transfer reaction

Sang Yong Pyun, Kyu Cheol Paik, Man So Han, Bong-Rae Cho

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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 languageEnglish
Pages (from-to)2810-2814
Number of pages5
JournalBulletin of the Korean Chemical Society
Volume36
Issue number12
DOIs
Publication statusPublished - 2015 Dec 1

Keywords

  • Bronsted and hammett plots
  • Concerted and stepwise mechanism
  • Nucleophilic substitution

ASJC Scopus subject areas

  • Chemistry(all)

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