C-(HO)-O-... hydrogen bonds in small ring carbonyl compounds: Vibrational spectroscopy and ab initio calculations
authors Vaz, PD; Ribeiro-Claro, PJA
nationality International
journal STRUCTURAL CHEMISTRY
author keywords C-(HO)-O-... hydrogen bonds; carbonyl stretching mode; isosbestic points; blue-shifted bands
keywords COMPLEX-FORMATION; PROPIONITRILE; IMPROPER; CRESOL
abstract The effect of the molecular structure on the properties of C-H... 0 bonds was investigated in a set of small cyclic carbonyl compounds, using vibrational spectroscopy and ab initio calculations. Two main effects were studied: the size of the ring and the inclusion of oxygen atoms in the ring. The analysis of the band profile of the carbonyl stretching mode reveals the presence of single dimerization equilibria in the series cyclobutanone-cyclopentanone-cyclohexanone. The smallest cyclobutanone was found to have the lowest dimerization energy, with an experimental Delta H value of 3.7 +/- 0.6 kJ mol(-1). The systems with oxygen atoms in the ring, gamma-butyrolactone and ethylene carbonate were found to present more complex equilibria. Ab initio calculations suggest that this complexity is due to the presence of additional dimer structures and higher oligomers.
publisher SPRINGER/PLENUM PUBLISHERS
issn 1040-0400
year published 2005
volume 16
issue 3
beginning page 287
ending page 293
digital object identifier (doi) 10.1007/s11224-005-4460-y
web of science category Chemistry, Multidisciplinary; Chemistry, Physical; Crystallography
subject category Chemistry; Crystallography
unique article identifier WOS:000230341800012
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journal impact factor 2.081
5 year journal impact factor 1.554
category normalized journal impact factor percentile 45.406
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