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Medicinal-Pharmaceutical Chemistry Commons

Open Access. Powered by Scholars. Published by Universities.®

2016

University of Nebraska - Lincoln

Thorpe-Ingold effect

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Ring Closures And The Hammond Postulate, Charles A. Kingsbury Jan 2016

Ring Closures And The Hammond Postulate, Charles A. Kingsbury

Faculty Publications -- Chemistry Department

This work reports an investigation of ring closure processes in relation to the Hammond postulate. Calculations favor the importance of thermodynamics, not kinetics, as the basis for the Hammond postulate. A kinetically rapid, but thermodynamically unfavorable reaction is shown to resemble product. The ease of ring closure to three-membered rings, compared to four-membered rings, is thought to be associated with conformational mobility and perhaps vibrations coupled to the reaction coordinate motion in the case of four-membered rings.