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Hydrolysis of amides. Kinetics and mechanism of the basic hydrolysis of N ‐acylpyrroles, N ‐acylindoles and N ‐acylcarbazoles
Author(s) -
Linda P.,
Stener A.,
Cipiciani A.,
Savelli G.
Publication year - 1983
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570200154
Subject(s) - chemistry , hydrolysis , steric effects , hydroxide , reactivity (psychology) , tetrahedral carbonyl addition compound , kinetics , medicinal chemistry , reaction rate constant , catalysis , organic chemistry , nucleophile , medicine , physics , alternative medicine , pathology , quantum mechanics
The hydroxide ion catalyzed hydrolysis of N ‐formyl, N ‐acetyl and N ‐benzoylpyrroles, ‐indoles and ‐carbazoles has been studied in water at 25.0°. The rate constants of formation of the tetrahedral intermediate are strongly increased by releasing steric hindrance in the acyl portion as shown by the higher reactivity of N ‐formyl derivatives in comparison with N ‐acetyl and N ‐benzoyl derivatives.