Models of F.H contacts relevant to the binding of fluoroaromatic inhibitors to carbonic anhydrase II.

[formula: see text] Complexes formed between fluorobenzene and N-methylformamide or benzene have been used as models of the interaction of fluoroaromatic drugs with carbonic anhydrase II. These structures have been investigated via ab initio and density functional methods, including HF, B3LYP, and MP2 procedures. The results of the calculations are consistent with the hypothesis, suggested originally by experimental X-ray crystal structures of the drug-receptor complexes, that favorable fluorine-hydrogen interactions affect binding affinity.