Magnitudes and Chemical Consequences of R3N+−C−H···OC Hydrogen Bonding
- 22 May 2002
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 124 (24) , 7163-7169
- https://doi.org/10.1021/ja012417q
Abstract
The magnitude of the stabilizing interaction between an aliphatic C−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 R3N+−C−H···OC interactions play an important role in supramolecular recognition and various types of stereoselective catalysis. Our calculations show that R3N+−C−H···OC 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.This publication has 87 references indexed in Scilit:
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