Magnitudes and chemical consequences of R(3)N(+)-C-H...O[double bond]C hydrogen bonding.
The magnitude of the stabilizing interaction between an aliphatic C[bond]H bond attached to an ammonium nitrogen and a carbonyl oxygen was evaluated by ab initio calculations at the MP2/6-311++G** level of theory. Attractive R(3)N(+)-C-H...O[double bond]C interactions play an important role in supramolecular recognition and various types of stereoselective catalysis. Our calculations show that R(3)N(+)-C-H...O[double bond]C is the strongest hydrogen bond of the C-H...O type known to date. Such hydrogen bonds remain as stabilizing interactions even in water for amide acceptors.
Cannizzaro
Carina E
CE
Department of Chemistry and Biochemistry, University of California, Los Angeles, California 90095-1569, USA.
Houk
K N
KN
D000085:Acetates / Q000737:chemistry*; D004126:Dimethylformamide / Q000737:chemistry*; D006860:Hydrogen Bonding; D008958:Models, Molecular; D008968:Molecular Conformation; D011789:Quantum Theory; D000644:Quaternary Ammonium Compounds / Q000737:chemistry*
D000085:Acetates; D000644:Quaternary Ammonium Compounds; D004126:Dimethylformamide; C046923:methyl acetate