title: Theoretical hydrogen bonding parameters for drug design.
abstract: 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.
authors.affiliation: Celltech Chiroscience Ltd., Granta Park, Great Abington, Cambridge CB1 6GS, UK. emanuela.gancia@celltechgroup.com
authors.forename: E
authors.initials: E
authors.lastname: Gancia
authors.forename: J G
authors.initials: JG
authors.lastname: Montana
authors.forename: D T
authors.initials: DT
authors.lastname: Manallack
mesh_terms: 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
chemical_list: D011522:Protons