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Updated: Jul 28, 2026

The Synthesis, Characterization and Reactivity of a Series of Ruthenium N-triphosPh Complexes
Published on: April 10, 2015
Magnitudes and chemical consequences of R(3)N(+)-C-H...O[double bond]C hydrogen bonding
Carina E Cannizzaro1, K N Houk
1Department of Chemistry and Biochemistry, University of California, Los Angeles, California 90095-1569, USA.
Abstract:
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.
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