Intramolecular hydrogen bonding analysis
Date
2022-05-04
Authors
Harville, Taylor
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Iowa State University Digital Repository, Ames IA (United States)
Abstract
The quasi-atomic orbital (QUAO) bonding analysis is used to study intramolecular hydrogen bonding (IMHB) in salicylic acid and an intermediate that is crucial to the synthesis of aspirin. The bonding analysis rigorously explores IMHB through directly accessing information that is intrinsic to the molecular wave function, thereby bypassing the need for intrinsically biased methods. The variables that affect the strength of IMHB are determined using kinetic bond orders, QUAO populations, and QUAO hybridizations. Important properties include both the interatomic distance between hydrogen and oxygen participating in the IMHB and the hybridization on the oxygen. The bonding analysis further shows that each intramolecular hydrogen bond is a four-electron three-center bond. The bonding analysis is used to understand how aromatic reactivity changes due to the effect of functional groups on the aromatic ring.
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IS-J 10791
IS-J 10815
IS-J 10928
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article
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This article appeared in Harville, Taylor, and Mark S. Gordon. "Intramolecular hydrogen bonding analysis." The Journal of Chemical Physics 156, no. 17 (2022): 174302, and may be found at
DOI: 10.1063/5.0090648.
Copyright 2022 Author(s).
Posted with permission.
DOE Contract Number(s): AC02-07CH11358