THE EFFECT OF ALKYL-GROUPS ON CARBANION STABILITY .1. INTERACTION OF SMALL RINGS WITH ADJACENT CARBANION CENTERS

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BALCIOGLU N., SEVIN F., EVIN O., PEYNIRCIOGLU N.

BERICHTE DER BUNSEN-GESELLSCHAFT-PHYSICAL CHEMISTRY CHEMICAL PHYSICS, vol.96, no.2, pp.139-142, 1992 (SCI-Expanded)

• Publication Type: Article / Article
• Volume: 96 Issue: 2
• Publication Date: 1992
• Doi Number: 10.1002/bbpc.19920960206
• Journal Name: BERICHTE DER BUNSEN-GESELLSCHAFT-PHYSICAL CHEMISTRY CHEMICAL PHYSICS
• Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED)
• Page Numbers: pp.139-142
• Middle East Technical University Affiliated: Yes

Abstract

Relative kinetic acidity measurements have shown that the cyclobutyl group has the ability to stabilize an adjacent carbanion center similar to vinyl and cyclopropyl groups, although to a lesser extent. The results of semiempirical calculations (MNDO) covering all the mentioned substituents, including the isopropyl group correlate well with the experimentally determined relative kinetic acidities.