Articles

Chemical Bond-Making, Bond-Breaking, and Electron Transfer in Solution

Science  26 Jan 1990:
Vol. 247, Issue 4941, pp. 423-430
DOI: 10.1126/science.247.4941.423

Abstract

A method is described for determining heats of heterolysis, ΔHhet, from the heats of reaction of resonancestabilized carbenium ions with carbanions in solution. These results can be converted into heats of homolysis, ΔHhomo, for the same bonds by combining ΔHhet values with electron transfer energies, δGETGET ≈ δHET), obtained from redox potentials of the reacting ions. The results provide a comprehensive tabulation of ΔHhet, ΔHhomo, and ΔGET values for an extended series of organic compounds and are examined in terms of their interrelationships and a number of related properties of the ions and radicals.

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