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Molecules 2017, 22(4), 552; doi:10.3390/molecules22040552

NMR and IR Investigations of Strong Intramolecular Hydrogen Bonds

Department of Science and Environment, Roskilde University, Universitetsvej 1, P.O. Box 260, DK-4000 Roskilde, Denmark
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Received: 1 February 2017 / Revised: 20 March 2017 / Accepted: 24 March 2017 / Published: 29 March 2017
(This article belongs to the Special Issue Intramolecular Hydrogen Bonding 2017)
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Abstract

For the purpose of this review, strong hydrogen bonds have been defined on the basis of experimental data, such as OH stretching wavenumbers, νOH, and OH chemical shifts, δOH (in the latter case, after correction for ring current effects). Limits for O–H···Y systems are taken as 2800 > νOH > 1800 cm−1, and 19 ppm > δOH > 15 ppm. Recent results as well as an account of theoretical advances are presented for a series of important classes of compounds such as β-diketone enols, β-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 β-diketone enols this correlation is relatively weak. View Full-Text
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 hydrogen bond strength; OH stretching wavenumbers; OH chemical shifts; isotope effects; tunneling splitting; O···O distances in O–H···O systems; Wiberg bond indices
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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Hansen, P.E.; Spanget-Larsen, J. NMR and IR Investigations of Strong Intramolecular Hydrogen Bonds. Molecules 2017, 22, 552.

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