On prediction of OH stretching frequencies in intramolecularly hydrogen bonded systems

Publikation: Bidrag til tidsskriftTidsskriftartikelForskningpeer review

Resumé

OH stretching frequencies are investigated for a series of non-tautomerizing systems with intramolecular hydrogen bonds. Effective OH stretching wavenumbers are predicted by the application of empirical correlation procedures based on the results of B3LYP/6-31G(d) theoretical calculations in the harmonic and PT2 anharmonic approximations, as well as on experimental NMR parameters, i.e., proton chemical shifts (δH) and two-bond deuterium isotope effects on 13C chemical shifts (2ΔCOD). The procedures are applied in a discussion of the spectra of 2,6-dihydroxy-4-methylbenzaldehyde and 8-hydroxyquinoline N-oxide. The spectrum of the former displays a broad, composite band between 3500 and 2500 cm−1 which can be assigned to overlapping monomer and dimer contributions. In the latter case, the results support a reassignment of the OH stretching band of 8-hydroxyquinoline N-oxide; the reassignment is supported by correlation with the IR spectra of a series of substituted derivatives.
OriginalsprogEngelsk
TidsskriftJournal of Molecular Structure: THEOCHEM
Vol/bind1018
Sider (fra-til)8-13
Antal sider6
ISSN0166-1280
DOI
StatusUdgivet - 27 jun. 2012

Citer dette

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title = "On prediction of OH stretching frequencies in intramolecularly hydrogen bonded systems",
abstract = "OH stretching frequencies are investigated for a series of non-tautomerizing systems with intramolecular hydrogen bonds. Effective OH stretching wavenumbers are predicted by the application of empirical correlation procedures based on the results of B3LYP/6-31G(d) theoretical calculations in the harmonic and PT2 anharmonic approximations, as well as on experimental NMR parameters, i.e., proton chemical shifts (δH) and two-bond deuterium isotope effects on 13C chemical shifts (2ΔCOD). The procedures are applied in a discussion of the spectra of 2,6-dihydroxy-4-methylbenzaldehyde and 8-hydroxyquinoline N-oxide. The spectrum of the former displays a broad, composite band between 3500 and 2500 cm–1 which can be assigned to overlapping monomer and dimer contributions. In the latter case, the results support a reassignment of the OH stretching band of 8-hydroxyquinoline N-oxide; the reassignment is supported by correlation with the IR spectra of a series of substituted derivatives.",
keywords = "OH stretching frequencies, Two-bond isotope effects, OH chemical shifts, DFT calculations, Intramolecular hydrogen bonding",
author = "Hansen, {Poul Erik} and Jens Spanget-Larsen",
year = "2012",
month = "6",
day = "27",
doi = "10.1016/j.molstruc.2012.01.011",
language = "English",
volume = "1018",
pages = "8--13",
journal = "Journal of Molecular Structure: THEOCHEM",
issn = "0166-1280",
publisher = "Elsevier BV",

}

On prediction of OH stretching frequencies in intramolecularly hydrogen bonded systems. / Hansen, Poul Erik; Spanget-Larsen, Jens.

I: Journal of Molecular Structure: THEOCHEM, Bind 1018, 27.06.2012, s. 8-13.

Publikation: Bidrag til tidsskriftTidsskriftartikelForskningpeer review

TY - JOUR

T1 - On prediction of OH stretching frequencies in intramolecularly hydrogen bonded systems

AU - Hansen, Poul Erik

AU - Spanget-Larsen, Jens

PY - 2012/6/27

Y1 - 2012/6/27

N2 - OH stretching frequencies are investigated for a series of non-tautomerizing systems with intramolecular hydrogen bonds. Effective OH stretching wavenumbers are predicted by the application of empirical correlation procedures based on the results of B3LYP/6-31G(d) theoretical calculations in the harmonic and PT2 anharmonic approximations, as well as on experimental NMR parameters, i.e., proton chemical shifts (δH) and two-bond deuterium isotope effects on 13C chemical shifts (2ΔCOD). The procedures are applied in a discussion of the spectra of 2,6-dihydroxy-4-methylbenzaldehyde and 8-hydroxyquinoline N-oxide. The spectrum of the former displays a broad, composite band between 3500 and 2500 cm–1 which can be assigned to overlapping monomer and dimer contributions. In the latter case, the results support a reassignment of the OH stretching band of 8-hydroxyquinoline N-oxide; the reassignment is supported by correlation with the IR spectra of a series of substituted derivatives.

AB - OH stretching frequencies are investigated for a series of non-tautomerizing systems with intramolecular hydrogen bonds. Effective OH stretching wavenumbers are predicted by the application of empirical correlation procedures based on the results of B3LYP/6-31G(d) theoretical calculations in the harmonic and PT2 anharmonic approximations, as well as on experimental NMR parameters, i.e., proton chemical shifts (δH) and two-bond deuterium isotope effects on 13C chemical shifts (2ΔCOD). The procedures are applied in a discussion of the spectra of 2,6-dihydroxy-4-methylbenzaldehyde and 8-hydroxyquinoline N-oxide. The spectrum of the former displays a broad, composite band between 3500 and 2500 cm–1 which can be assigned to overlapping monomer and dimer contributions. In the latter case, the results support a reassignment of the OH stretching band of 8-hydroxyquinoline N-oxide; the reassignment is supported by correlation with the IR spectra of a series of substituted derivatives.

KW - OH stretching frequencies

KW - Two-bond isotope effects

KW - OH chemical shifts

KW - DFT calculations

KW - Intramolecular hydrogen bonding

U2 - 10.1016/j.molstruc.2012.01.011

DO - 10.1016/j.molstruc.2012.01.011

M3 - Journal article

VL - 1018

SP - 8

EP - 13

JO - Journal of Molecular Structure: THEOCHEM

JF - Journal of Molecular Structure: THEOCHEM

SN - 0166-1280

ER -