Electrostatic potential, molecular interactive hydrogen bond acceptor

The physical basis for this supramolecular motif can be ascribed to a desire of the system to maximize electrostatic interactions. The pyridyl nitrogen atom and the -OH moiety constitute the best hydrogen-bond acceptor and donor,respectively, and these moieties display a strong preference for each other. The key to understanding and predicting the supramolecular behavior of a family of (N-heterocycle/amide) SRs is the relative hydrogen-bonding (HB) ability" (based on basicity and molecular electrostatic surface potential) of the N-heterocycle (Scheme 4). 

One of the early applications of molecular electrostatic potentials was in relation to hydrogen bonding. The Fm n (most negative potentials) were found to be effective in identifying sites at which hydrogen bonds would be accepted [16,89-91]. Furthermore, Kollman et al. [89] showed that the calculated energy of the interaction between hydrogen fluoride and a series of acceptors correlates well with the value of V(r) at a fixed distance from the latter. 

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