Supplementary Material Available: Spectral and analytical data for the addition products (£)-and (Z)-2am, (E)-2bm, (E)-2cm, 2an,ar,bn,bo,br,bs,cr,dr,em,er, and 3 am,an,at,bm,bn,bp,bq,cm,dm,em,frn,gm (8 pages). Ordering information is given on any current masthead page.

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A simple "master equation" for predicting the heterolysis energies of bonds to give resonancestabilized ions is tested by reaction of six carbocations with 21 carbanions and four phenoxide anions. The original equation31" is enormously improved in precision and generality by replacing pAR+ values as the measure of cation stability. If calculated delocalization energies are used, data for 33 reactions are correlated by eq 5 with r = 0.9948 (instead of r = 0.8812) so that the standard deviation of AHhet is ± 0.702 kcal/mol. With Mfhet for 9-(methoxycarbonyl)fluorenide anion as the model anion, 66 values are correlated with r = 0.9960, proving the self-consistency of our data as well as the soundness of this approach. Equations such as (5) should provide a simple means for estimating quantitative heterolysis energies in solution for thousands of bonds that give resonance-stabilized ions as products. 9-CNRH 8.30

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