Hydrolysis of amides. Kinetics and mechanism of the basic hydrolysis of  N ‐acylpyrroles,  N ‐acylindoles and  N ‐acylcarbazoles | Zendy

Linda P. | Zendy; Stener A. | Zendy; Cipiciani A. | Zendy; Savelli G. | Zendy

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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.

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