NMR and IR investigations of strong intramolecular hydrogen bonds

Publikation: Bidrag til tidsskriftReviewForskningpeer review

Resumé

For the purpose of this review, strong hydrogen bonds have been defined on the basis of experimental data, such as OH stretching wavenumbers, vOH, and OH chemical shifts, dOH (in the latter case after correction for ring current effects). Limits for O–H···Y systems are taken as 2800 > vOH > 1800 cm–1, and 19 >  dOH > 15 ppm. Recent results as well as an account of theoretical advances are presented for a series of important classes of compounds such as beta-diketone enols, beta-thioxoketone enols, Mannich bases, proton sponges, quinoline N-oxides and diacid anions. The O···O distance has long been used as a parameter for hydrogen bond strength in O–H···O systems. On a broad scale, a correlation between OH stretching wavenumbers and O···O distances is observed, as demonstrated experimentally as well as theoretically, but for substituted beta-diketone enols this correlation is relatively weak.
OriginalsprogEngelsk
TidsskriftMolecules
Vol/bind22
Udgave nummer4
Sider (fra-til)552
ISSN1420-3049
DOI
StatusUdgivet - 29 mar. 2017

Citer dette

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title = "NMR and IR investigations of strong intramolecular hydrogen bonds",
abstract = "For the purpose of this review, strong hydrogen bonds have been defined on the basis of experimental data, such as OH stretching wavenumbers, vOH, and OH chemical shifts, dOH (in the latter case after correction for ring current effects). Limits for O–H···Y systems are taken as 2800 > vOH > 1800 cm–1, and 19 >  dOH > 15 ppm. Recent results as well as an account of theoretical advances are presented for a series of important classes of compounds such as beta-diketone enols, beta-thioxoketone enols, Mannich bases, proton sponges, quinoline N-oxides and diacid anions. The O···O distance has long been used as a parameter for hydrogen bond strength in O–H···O systems. On a broad scale, a correlation between OH stretching wavenumbers and O···O distances is observed, as demonstrated experimentally as well as theoretically, but for substituted beta-diketone enols this correlation is relatively weak.",
keywords = "Hydrogen bond strength. , OH stretching wavenumbers. , OH chemical shifts, Isotope effects, Tunneling splitting, O···O distances in O–H···O systems, Wiberg bond indices",
author = "Hansen, {Poul Erik} and Jens Spanget-Larsen",
note = "Contribution to Special Issue of {"}Molecules{"}: Intramolecular Hydrogen Bonding 2017",
year = "2017",
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day = "29",
doi = "10.3390/molecules22040552",
language = "English",
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NMR and IR investigations of strong intramolecular hydrogen bonds. / Hansen, Poul Erik; Spanget-Larsen, Jens.

I: Molecules, Bind 22, Nr. 4, 29.03.2017, s. 552.

Publikation: Bidrag til tidsskriftReviewForskningpeer review

TY - JOUR

T1 - NMR and IR investigations of strong intramolecular hydrogen bonds

AU - Hansen, Poul Erik

AU - Spanget-Larsen, Jens

N1 - Contribution to Special Issue of "Molecules": Intramolecular Hydrogen Bonding 2017

PY - 2017/3/29

Y1 - 2017/3/29

N2 - For the purpose of this review, strong hydrogen bonds have been defined on the basis of experimental data, such as OH stretching wavenumbers, vOH, and OH chemical shifts, dOH (in the latter case after correction for ring current effects). Limits for O–H···Y systems are taken as 2800 > vOH > 1800 cm–1, and 19 >  dOH > 15 ppm. Recent results as well as an account of theoretical advances are presented for a series of important classes of compounds such as beta-diketone enols, beta-thioxoketone enols, Mannich bases, proton sponges, quinoline N-oxides and diacid anions. The O···O distance has long been used as a parameter for hydrogen bond strength in O–H···O systems. On a broad scale, a correlation between OH stretching wavenumbers and O···O distances is observed, as demonstrated experimentally as well as theoretically, but for substituted beta-diketone enols this correlation is relatively weak.

AB - For the purpose of this review, strong hydrogen bonds have been defined on the basis of experimental data, such as OH stretching wavenumbers, vOH, and OH chemical shifts, dOH (in the latter case after correction for ring current effects). Limits for O–H···Y systems are taken as 2800 > vOH > 1800 cm–1, and 19 >  dOH > 15 ppm. Recent results as well as an account of theoretical advances are presented for a series of important classes of compounds such as beta-diketone enols, beta-thioxoketone enols, Mannich bases, proton sponges, quinoline N-oxides and diacid anions. The O···O distance has long been used as a parameter for hydrogen bond strength in O–H···O systems. On a broad scale, a correlation between OH stretching wavenumbers and O···O distances is observed, as demonstrated experimentally as well as theoretically, but for substituted beta-diketone enols this correlation is relatively weak.

KW - Hydrogen bond strength.

KW - OH stretching wavenumbers.

KW - OH chemical shifts

KW - Isotope effects

KW - Tunneling splitting

KW - O···O distances in O–H···O systems

KW - Wiberg bond indices

U2 - 10.3390/molecules22040552

DO - 10.3390/molecules22040552

M3 - Review

VL - 22

SP - 552

JO - Molecules

JF - Molecules

SN - 1420-3049

IS - 4

ER -