General‐base catalysed hydrolysis and nucleophilic substitution of activated amides in aqueous solutions | Zendy

Buurma Niklaas J. | Zendy; Blandamer Michael J. | Zendy; Engberts Jan B. F. N. | Zendy

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General‐base catalysed hydrolysis and nucleophilic substitution of activated amides in aqueous solutions

Author(s) -

Buurma Niklaas J.,

Blandamer Michael J.,

Engberts Jan B. F. N.

Publication year - 2003

Publication title -

journal of physical organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.325

H-Index - 66

eISSN - 1099-1395

pISSN - 0894-3230

DOI - 10.1002/poc.607

Subject(s) - chemistry , nucleophile , reactivity (psychology) , nucleophilic substitution , base (topology) , aqueous solution , medicinal chemistry , hydrolysis , intramolecular force , substitution reaction , leaving group , catalysis , combinatorial chemistry , organic chemistry , medicine , mathematical analysis , alternative medicine , mathematics , pathology

The reactivity of 1‐benzoyl‐3‐phenyl‐1,2,4‐triazole ( 1a ) was studied in the presence of a range of weak bases in aqueous solution. A change in mechanism is observed from general‐base catalysed hydrolysis to nucleophilic substitution and general‐base catalysed nucleophilic substitution. A slight tendency is also observed for the more hydrophobic general bases to show higher reactivity towards 1a . Aspartame is an effective nucleophile, possibly because nucleophilic substitution is subject to intramolecular general‐base catalysis. A general conclusion derived from the present results is that unexpected rate effects can only be rationalised provided that the detailed reaction mechanisms are well understood. Copyright © 2003 John Wiley & Sons, Ltd.

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