Intramolecular hydrogen bonding in cycloalkane-1,2-diol monoacetates

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Abstract
Intramolecular hydrogen bonding in cyclopentane- and cyclohexane-1,2-diol monoacetates was studied by high resolution infrared spectroscopy in the 3μ region. Intramolecular hydrogen bonding was exhibited by all compounds and the data are interpreted in terms of preferred conformations, assuming the acetate group to be exclusively in the "planar trans" form.trans-Cyclopentane-1,2-diol monoacetate exhibited two hydroxyl absorption bands. One band was assigned to free hydroxyl stretching and the other to hydrogen bonding with the carbonyl oxygen so that an equilibrium between two ring conformations must be assumed to exist in solution. With cis-cyclopentane-1,2-diol monoacetate only a strong high frequency band was observed, and this was attributed to hydrogen bonding to the alkoxyl oxygen.trans- and cis-cyclohexane-1,2-diol monoacetate both exhibited two hydroxyl absorption bands. With the former, the hydroxyl group was assumed to be exclusively in an equatorial position to permit hydrogen bonding to both the alkoxyl and carbonyl oxygens. Similarly, in the latter, the high frequency band was attributed to hydrogen bonding to the alkoxyl oxygen atom while the low frequency band was assigned to hydrogen bonding to the carbonyl oxygen.

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