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Intrinsic proton affinity of substituted aromatics

1998; Elsevier BV; Linguagem: Inglês

10.1016/s1380-7323(98)80010-1

2212-1617

Zvonimir B. Maksić, Mirjana Eckert‐Maksić,

DNA and Nucleic Acid Chemistry

It is shown that the MP2(fc)/6-31G*//HF/6-31G*+ZPE (HF)/6-31G*) model reproduces very well the experimental proton affinities in a large number of substituted benzenes and naphthalenes. Extensive applications of this model revealed that the proton affinity of polysubstituted aromatics followed a simple additivity rule, which have been rationalized by the ISA (independent substitutent approximation) model. Performance of this model is surprisingly good. Applications of proton affinities, obtained by the transparent and intuitively appealing ISA model, in interpreting directional ability of substituents in the electrophilic substitution reactions of aromatics are briefly discussed.