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The efficiency of intramolecular general base catalysis in nonaqeous solvents

✍ Scribed by Anthony J. Kirby; Koh Lip Lin

Publisher: Elsevier Science
Year: 1978
Tongue: French
Weight: 114 KB
Volume: 19
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(01)95145-7

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✦ Synopsis

There is good evidence that intramolecular general base catalysis is much less efficient than intramolecular nucleophilic catalysis.' It has recently been suggested' that this is true only for reactions in aqueous solvents, and that in nonaqueous solvents -and perhaps also in enzyme active sites from which water is excluded -intramolecular general base catalysis may cause large rate acceleraticns.

This conclusion was based on data for the n-butylaminolysis of 2-hydroxyphenyl benzoate (A), and the corresponding methoxy compound (2>, in acetonitrile.

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