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The O···H intramolecular hydrogen bond in 4‐X‐2‐hydroxybenzaldehydes: The relationships between geometrical parameters, estimated binding energies, and NMR data
Author(s) -
Ebrahimi A.,
Khorasani S. M. Habibi,
Neyband R. S.
Publication year - 2009
Publication title -
international journal of quantum chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.484
H-Index - 105
eISSN - 1097-461X
pISSN - 0020-7608
DOI - 10.1002/qua.22339
Subject(s) - intramolecular force , chemistry , hydrogen bond , atoms in molecules , molecule , ring (chemistry) , bond length , binding energy , natural bond orbital , computational chemistry , resonance (particle physics) , crystallography , density functional theory , atomic physics , stereochemistry , physics , organic chemistry
The relationships among geometrical parameters, estimated binding energies, and nuclear magnetic resonance data in –CO···HO intramolecular H‐bond of some substituted 2‐hydroxybenzaldehyde have theoretically been studied by B3LYP and MP2 methods with 6‐311++G** and AUG‐cc‐PVTZ basis sets. All substituents increase estimated hydrogen bond energies E HB s (with the exception of NO 2 and C 2 H 5 ), which are in good correlation with geometrical parameters, topological properties of electron density calculated at O···H bond critical points and ring critical points by using atoms in molecules method, the results of natural bond orbital analysis, and calculated nuclear magnetic resonance data. © 2009 Wiley Periodicals, Inc. Int J Quantum Chem, 2010