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  Home > JCE Print > Journal of Chemical Education > Issues > 1999  > September  >
In the Laboratory
Electrophilic Substitution in Naphthalene: Kinetic vs Thermodynamic Control
Leslie D. Field, Sever Sternhell, and Howard V. Wilton
The University of Sydney, Division of Organic Chemistry, Sydney, N.S.W. 2006, AUSTRALIA
Cover
September 1999
Vol. 76 No. 9
p. 1246
Abstract
Deuterium-protium exchange in naphthalene effected by trifluoroacetic acid and aluminium tris-trifluoroacetate was followed by proton NMR spectroscopy. Initially, the partly deuterated naphthalene has a ratio of protium to deuterium at the C-1 (a) position smaller than unity, reflecting a higher reactivity towards electrophiles at this position. However, after equilibrium has been established, this ratio becomes unity within the experimental accuracy of the measurement, reflecting the lack of any thermodynamic effect. These results are a potential "textbook" example of kinetic versus thermodynamic control, which is much clearer than the usually quoted reversible sulfonation of naphthalene.
More Information
*  Citation
 Field, Leslie D.; Sternhell, Sever; Wilton, Howard V. J. Chem. Educ. 1999 76 1246.
*  Keywords
 Organic Chemistry; Kinetics; Thermodynamics; Mechanisms; NMR Spectrometry
*  History
 Created:
Last Updated:		 July 30, 1999
June 23, 2005
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