Intramolecular Hydrogen Bonding in 2-Hydroxybenzoyl Compounds: Infrared Spectra and Quantum Chemical Calculations

Autor:	Alfred Karpfen, Heike Lampert, Werner Mikenda,† and
Rok vydání:	1996
Předmět:	Quantum chemical Force constant Partial charge Calculated data Chemistry Hydrogen bond Intramolecular force General Engineering Physical chemistry Infrared spectroscopy chemistry.chemical_element Physical and Theoretical Chemistry Oxygen
Zdroj:	The Journal of Physical Chemistry. 100:7418-7425
ISSN:	1541-5740 0022-3654
DOI:	10.1021/jp953527k
Popis:	IR gas-phase and quantum chemical data that characterize the intramolecular hydrogen bonds in a series of 2-hydroxybenzoyl compounds (Ph(OH)(COY): Y = Cl, OH, SH, OCH3, SCH3, H, CH3, Ph, N(CH(CH3)CH2)2CH2, N(CH2CH2)2CH2, N(CH3)2, NHCH3, NH2, NHNH2) are reported and discussed. The sequences of ν(OH) and of ν(CO) frequencies calculated at HF/3-21G, HF/6-31G**, and B3LYP/6-31G** computational levels agree reasonably well with the corresponding experimental sequences. The consistency of the calculated data is demonstrated by exploiting several relations between calculated frequencies, force constants, and bond distances. It is shown that the sequence of hydrogen bond strengths, as defined either by ν(OH) frequency shifts or by R(O−H) bond distances, may qualitatively be interpreted in terms of two quantities, the R(H···O) hydrogen bond distances and the Q(O) oxygen partial charges, which characterize the intrinsic differences between the carbonyl groups.
Databáze:	OpenAIRE
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