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  Home > JCE Print > Journal of Chemical Education > Issues > 1996  > November  >
Research: Science and Education
The Role of Electrostatic Effects in Organic Chemistry
Kenneth B. Wiberg
Department of Chemistry, Yale University, New Haven, CT 06529-8107
Cover
November 1996
Vol. 73 No. 11
p. 1089
Abstract
Electrostatic effects on the properties of organic compounds are reviewed to demonstrate the importance of electronegativity differences between the atoms forming a bond. Bond dissociation energies are generally found to increase as the electronegativity difference increases, and the bonds have increased ionic character. The stabilization of polyfluorinated compounds arises in a similar fashion, with the positive charge at carbon increasing linearly with the number of fluorines. The carbonyl group is strongly polarized, and substituents that take electron density from the carbon will lead to a stronger electrostatic interaction in the carbonyl group, resulting in a decrease in energy. The application of these ideas to amide resonance, the acidity of carboxylic acids and substituent effects at vinyl groups are discussed.
More Information
*  Citation
 Wiberg, Kenneth B. J. Chem. Educ. 1996 73 1089.
*  Keywords
 organic, physical/theoretical, electronegativity
*  History
 Created:
Last Updated:		 August 5, 1999
February 21, 2006
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