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

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

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

  • Publication Type: Article / Article
  • Volume: 96 Issue: 2
  • Publication Date: 1992
  • Doi Number: 10.1002/bbpc.19920960206
  • Title of Journal : BERICHTE DER BUNSEN-GESELLSCHAFT-PHYSICAL CHEMISTRY CHEMICAL PHYSICS
  • Page Numbers: pp.139-142

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.