Article: Symmetry of hydrogen bonds in solution.(Report)

INTRODUCTION

Hydrogen bonds (H-bonds) are a key feature of molecular structure [1]. A classic question regarding the structure of H-bonds concerns their symmetry. If the two donor atoms, A and B, have the same proton affinity, is the hydrogen centered (A**H**B) or is it closer to one and jumping between them (A-H***B in rapid equilibrium with A...H-B)? These two possibilities correspond to single- and double-well potentials, respectively (Fig. 1). Representative examples of these are maleate (1a) and phthalate (1b) monoanions and enols of acetylacetone (2), respectively.

[FIGURE 1 OMITTED]

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