Title
The Nature of the Hydrogen Bond: Outline of a Comprehensive Hydrogen Bond Theory (International Union of Crystallography Monogra,Used
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Hydrogen bond (Hbond) effects are known: it makes sea water liquid, joins cellulose microfibrils in trees, shapes DNA into genes and polypeptide chains into wool, hair, muscles or enzymes. Its true nature is less known and we may still wonder why OH...O bond energies range from less than 1 to more than 30 kcal/mol without apparent reason. This Hbond puzzle is reexamined here from its very beginning on the ground of an inclusive compilation of experimental Hbond energies and geometries.New concepts emerge from this analysis: new classes of systematically strong Hbonds (CAHBs and RAHBs: charge and resonanceassisted Hbonds); full Hbond classification in six classes (the six chemical leitmotifs); and assessment of the covalent nature of strong Hbonds. This leads to three distinct but interconsistent models able to rationalize the Hbond and predict its strength, based on classical VB theory, matching of donoracceptor acidbase parameters (PA or pKa), or shape of the Hbond protontransfer pathway.Applications survey a number of systems where strong Hbonds play an important functional role, namely drugreceptor binding, enzymatic catalysis, iontransport through cell membranes, crystal design and molecular mechanisms of functional materials.
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