Skip to Main content Skip to Navigation
Journal articles

Microwave and Quantum-Chemical Study of Conformational Properties and Intramolecular Hydrogen Bonding of 2-Hydroxy-3-Butynenitrile (HC≡CCH(OH)C≡N)

Abstract : The microwave spectra of 2-hydroxy-3-butynenitrile, HC≡CCH(OH)C≡N, and a deuterated species, HC≡CCH(OD)C≡N, have been investigated in the 38-120 GHz spectral region. Three rotameric forms, each stabilized by intramolecular hydrogen bonds, are possible for this compound. The hydrogen atom of the hydroxyl group is hydrogen-bonded to the π electrons of the alkynyl group in one of these conformers, to the π electrons of the cyano group in the second rotamer, and to both of these groups simultaneously in the third conformer. The microwave spectra of the parent and deuterated species of last-mentioned form have been assigned, and accurate values of the rotational and quartic centrifugal distortion constants of these species have been determined. The spectra of two vibrational excited states of this conformer have also been assigned, and their frequencies have been determined by relative intensity measurements. Quantum-chemical calculations at the MP2/cc-pVTZ and CCSD/cc-pVQZ levels were performed to assist the microwave work. The theoretical predictions were generally found to be in good agreement with observations.
Document type :
Journal articles
Complete list of metadatas

https://hal-univ-rennes1.archives-ouvertes.fr/hal-01133057
Contributor : Laurent Jonchère <>
Submitted on : Wednesday, March 18, 2015 - 2:29:37 PM
Last modification on : Monday, March 9, 2020 - 4:58:04 PM

Identifiers

Citation

Harald Møllendal, Svein Samdal, Jean-Claude Guillemin. Microwave and Quantum-Chemical Study of Conformational Properties and Intramolecular Hydrogen Bonding of 2-Hydroxy-3-Butynenitrile (HC≡CCH(OH)C≡N). Journal of Physical Chemistry A, American Chemical Society, 2015, 119 (4), pp.634-40. ⟨10.1021/jp5112923⟩. ⟨hal-01133057⟩

Share

Metrics

Record views

376