On prediction of OH stretching frequencies in intramolecularly hydrogen bonded systems

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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

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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",
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    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 -