Canadian Journal of Chemistry

General Base Catalysis of β Elimination by a Steroidal Enzyme Model

JP Guthrie, S O'Leary

文献索引：Guthrie,J.P.; O'Leary,S. Canadian Journal of Chemistry, 1975 , vol. 53, p. 2150 - 2156

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被引用次数: 16

摘要

The water soluble steroid 1 acts as a catalyst for the enolization of the ketones 2 ac. The rate enhancement for 1-catalyzed reaction relative to imidazole-catalyzed reaction (R), increases as the size of the aromatic ring system of the substrate increases; a plot of log R vs π has a slope of 0.43. This is interpreted in terms of hydrophobic binding between steroid α-surface and aromatic ring system which lowers the free energy level of the transition state for ...