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Conformation and Stability of the Hydrogen-Bonded Complex 6-Oxabicyclo[3.1.0]hexane⋅⋅⋅HCl

✍ Scribed by Sonia Antolínez; Alberto Lesarri; Juan C. López; José L. Alonso

Publisher
John Wiley and Sons
Year
2000
Tongue
English
Weight
143 KB
Volume
6
Category
Article
ISSN
0947-6539

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✦ Synopsis

The hydrogen-bonded complex between 6-oxabicyclo[3.1.0]hexane and hydrogen chloride was investigated by microwave spectroscopy in a supersonic jet. A dual flow pulsed valve was used to preclude chemical reaction between the monomers. Only the equatorial conformer was observed and the spectra of three isotopomers, (C5H8O, H35Cl), (C5H8O, H37Cl) and (C5H8O, D35Cl), were measured. The derived structure of the complex has Cs symmetry with the hydrogen chloride pointing to the domain of the equatorial lone pair of electrons at the oxygen atom. The three atoms involved in the hydrogen bond adopt a bent arrangement with a O...H distance of 1.77(4) A, a (O...H-Cl) angle of 115(4)degrees, and a deviation of 15.4(14)degrees of the hydrogen bond from collinearity. In agreement with the experimental results, ab initio calculations predict the equatorial form to be the most stable one.

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The crystal structure of the title compound (3) was determined by the X-ray diffraction technique from diffractometer intensity measurements: C,H, O& monoclin{c space group P2, c, a = 12.644( 1) A, b = 6.102(1) A, c = 12.920(2) 1, B = 110.78(1)", 2193 reflections, and R = 0.043. The molecule of 3 ad