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Unexpected nonadditivity effects in anion-π complexes.

Several complexes of fluorine-substituted ethyne, ethene, butadiene, benzene, and [n]radialenes (n = 3-5) with two anions have been optimized at the RI-MP2/aug-cc-pVTZ level of theory. The additivity of the anion-π interaction was studied depending on the number of double bonds and fluorine atoms. Interesting nonadditivity effects were observed in the aromatic and antiaromatic complexes, which were analyzed by partitioning the total interaction energy into individual components, using Bader's theory of "atoms in molecules" and changes in the aromatic character of the ring upon complexation.