title: Electrostatic interaction of pi-acidic amides with hydrogen-bond acceptors.
abstract: Interactions between N-methylacetamide (NMA) and N-methylated derivatives of uracil, isocyanurate and barbituric acid have been studied using ab initio methods at the local MP2/6-31G** level of theory. The results were compared to similar interactions between the oxygen atom of NMA and the pi-clouds of perfluorobenzene, quinone and trimethyltriazine. The pi-acidic amides of isocyanurate and barbituric acid were found to interact with a hydrogen bond acceptor primarily through electrostatic attractions. These groups may be used as alternatives of a hydrogen bond donor to complement a hydrogen bond acceptor or an anion in molecular recognition and drug design. Examples of such interactions were identified through a search of the CSD database.
authors.affiliation: Computer-Assisted Drug Design, The Bristol-Myers Squibb Pharmaceutical Research Institute, 5 Research Parkway, Wallingford, CT 06492, USA. yi.li@aventis.com
authors.forename: Yi
authors.initials: Y
authors.lastname: Li
authors.forename: Lawrence B
authors.initials: LB
authors.lastname: Snyder
authors.forename: David R
authors.initials: DR
authors.lastname: Langley
mesh_terms: D000577:Amides / Q000737:chemistry* / Q000378:metabolism*; D006860:Hydrogen Bonding / Q000187:drug effects; D055672:Static Electricity
chemical_list: D000577:Amides