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Issue 31, 2011
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Intramolecular OH⋯π interactions in alkenols and alkynols

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Abstract

The vibrational overtone spectra of propargyl alcohol (prop-2-yn-1-ol, PA), allyl alcohol (prop-2-en-1-ol, AA), propargyl carbinol (but-3-yn-1-ol, PC) and allyl carbinol (but-3-en-1-ol, AC) were recorded with intracavity laser photoacoustic spectroscopy (ICL-PAS) in the ΔvOH = 3, 4 and 5 regions for propargyl alcohol and allyl alcohol and in the ΔvOH = 4 and 5 regions for propargyl carbinol and allyl carbinol. Local mode anharmonic oscillator calculations were performed with explicitly correlated coupled cluster methods to guide spectral assignment. Atoms in molecules (AIM) and non-covalent interactions (NCI) calculations were carried out to analyze the interactions between the OH-group and the π-electrons of the carbon–carbon multiple bonds. We ascertain the effect of the carbon chain length and saturation on the conformation and spectroscopy of the four alcohols in relation to intramolecular hydrogen bonding interactions.

Graphical abstract: Intramolecular OH⋯π interactions in alkenols and alkynols

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Submitted
15 Apr 2011
Accepted
20 Jun 2011
First published
08 Jul 2011

Phys. Chem. Chem. Phys., 2011,13, 14183-14193
Article type
Paper

Intramolecular OH⋯π interactions in alkenols and alkynols

B. J. Miller, J. R. Lane and H. G. Kjaergaard, Phys. Chem. Chem. Phys., 2011, 13, 14183
DOI: 10.1039/C1CP21190K

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