Schmeer, Georg and Six, C. and Steinkirchner, J. (1999) Investigations on substituent and solvent effects of solvolysis reactions. VIII. The influence of water and nonaqueous solvents on the imidazolysis of 4-nitrophenyl acetate. JOURNAL OF SOLUTION CHEMISTRY, 28 (3). pp. 211-222. ISSN 0095-9782,
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The aminolysis reaction of 4-nitrophenyl acetate with imidazole was investigated in water, acetonitrile, propylene carbonate, and 1,4-dioxane at different temperatures, the observed rates can be evaluated with the help of a reaction mechanism consisting of two competitive reaction paths; the first is the bimolecular nucleophilic substitution of the phenol moiety by imidazole; the second path is performed via general base catalysis by a second imidazole molecule. The rate constants of the bimolecular reaction are quantitatively correlated with the four-parameter Taft-Kamlet equation for solvent effects on chemical reactions. A qualitative interpretation of the data shows that the two reaction paths are influenced to the same extent by the solvent.
| Item Type: | Article |
|---|---|
| Uncontrolled Keywords: | SOLVATOCHROMIC COMPARISON METHOD; GENERAL BASE CATALYSIS; N-ACYLIMIDAZOLES; ESTER AMINOLYSIS; LEAVING GROUP; PI-STAR; HYDROLYSIS; MECHANISMS; PYRIDINES; SOLVATION; 4-nitrophenyl acetate; imidazolysis; solvent effect; Taft-Kamlet parameters |
| Subjects: | 500 Science > 540 Chemistry & allied sciences |
| Divisions: | Chemistry and Pharmacy > Institut für Physikalische und Theoretische Chemie > Alumni or Retired Professors > Prof. Dr. Georg Schmeer |
| Depositing User: | Dr. Gernot Deinzer |
| Date Deposited: | 15 Nov 2022 11:19 |
| Last Modified: | 15 Nov 2022 11:19 |
| URI: | https://pred.uni-regensburg.de/id/eprint/48475 |
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