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hydrogen bond

An important cohesive force of biological macromolecules, notably interstrand interactions of bases in the Watson-Crick model of DNA and of amide groups in the -helix of proteins. The bond is the attraction of a weak acid to a weak base due to the sharing of a proton between them, e.g. -OH…O=, ;NH…O=. The sharing may be considered to be an equilibrium between two tautomeric forms, e.g. -O-…HO+=, each form lying in an energy well with an energy barrier between them (the double-well hydrogen bond). If water is excluded from the area, and if the base strengths of the two atoms that share the proton are equal, the distance between the two nucleophilic atoms is shorter and the bond is much stronger [;100kJ/mol (24kcal/mol); the single-well hydrogen bond]. An intermediate case pertains [50-100kJ/mol (12-24 kcal/mol); the low-barrier hydrogen bond] when the pKa values of the nucleophiles are similar and water is largely excluded, as at the active site of an enzyme in the transition state with its substrate.Cleland, W.W. and Kreevoy, M.M. (1994) Science 264, 1887-1890; Frey, P.A., Whitt, S.A. and Tobin, J.B. (1994) Science 264, 1927-1930

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