Abstract
Separate peaks at δ 13.0 and 7.5 are observed for the intramolecularly hydrogen-bonded and nonhydrogen-bonded hydroxy groups in the 1H n.m.r. spectrum of 2-phenylazoresorcinol in [2H8]toluene at temperatures below ca. 300 K. At 357 K, equilibration of the two conformers in which the phenylazo group is hydrogen-bonded to each hydroxy group is rapid (k 5.4 × 104 s–1) and an averaged hydroxy peak at δca. 10 is observed. Energy barriers for substituted 2-phenylazoresorcinols in [2H8]toluene and CD2Cl2 have been obtained from linewidth measurements of the hydroxy peaks and from observation of coalescence temperatures of aromatic 1H and 13C signals.
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Schedule a callMore From: Journal of the Chemical Society, Perkin Transactions 2
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