Abstract
THE hydrogen bond is usually described as unsymmetrical, with the hydrogen atom nearer one of the two bonding atoms, and the energy of bonding is considered as due to electrostatic and delocalization energy. The principal valency bond structures considered are I, II and III, and it has been shown1 that when the O—O distance is 2.5 A. these three structures have the relative weights 60.3, 28.4 and 11.3. Resonance of a purely covalent character is not considered to play a part as this would require the hydrogen atom to be symmetrically placed between the two bonded atoms, and Donohue2, by extrapolating Pauling's bond-order/bond-length relationship, has calculated that for such a bond the O—O distance could not exceed 2.4 A. However, most of the detailed studies of this problem have been concerned with intermolecular hydrogen bonds, and it is suggested here that in the cyclic systems involved in intramolecular hydrogen bonds, covalent forces play a much larger part. 
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GILL, E., MORGAN, E. Intramolecular Hydrogen Bonding in Heterocyclic Systems. Nature 183, 248–249 (1959). https://doi.org/10.1038/183248a0
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DOI: https://doi.org/10.1038/183248a0
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