Infrared−ultraviolet double-resonance spectroscopy has been applied to discriminate rotamers of jet-cooled aryl alcohol homologues, φ-(CH2)nOH, where φ represents phenyl group and n = 1, 2, and 3 correspond to benzyl, phenethyl, and 3-phenylpropyl alcohols, respectively. Experimental results indicate that different OH stretching frequencies are associated with different rotamers and that the ability of intramolecular hydrogen bonding with the benzene π-electron decreases with an increase in alkyl chain length. In each aryl alcohol, the most prominent species in jets corresponds to the non-hydrogen-bonded rotamer having higher OH stretching frequency.
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Guchhait et al. (1999) studied this question.
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