Theoretical hydrogen bonding parameters for drug design.
Hydrogen bonding interactions play a major role in many chemical and biological processes. This article describes the development of a method for the quantitative estimation of the hydrogen-bonding donor strengths of OH/NH moieties and of the hydrogen bonding acceptor strengths of O/N atoms in different chemical structures. The method is based on the correlation of experimentally observed hydrogen-bonding strengths with quantum-mechanical derived properties, calculated on the acceptor atom (for hydrogen-bond acceptors) and on the heavy atom attached to the donor hydrogen (for hydrogen-bond donors). The properties giving the best correlation with the experimental hydrogen bonding scales were electrophilic superdelocalizability and self-atom polarizability. The best equations found have been implemented in a Web-based tool for hydrogen-bond strength prediction.
Gancia
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Celltech Chiroscience Ltd., Granta Park, Great Abington, Cambridge CB1 6GS, UK. emanuela.gancia@celltechgroup.com
Montana
J G
JG
Manallack
D T
DT
D003196:Computer Graphics; D003198:Computer Simulation; D019992:Databases as Topic; D015195:Drug Design; D006860:Hydrogen Bonding; D008956:Models, Chemical; D011522:Protons; D011789:Quantum Theory; D012984:Software
D011522:Protons