Abstract
The electronic absorption spectra of salicylanilide and eight of its derivatives (with substituents o-OCH 3, o-Cl (a), m-OH, m-OCH 3, p-Cl, p-OH, p-OCH 3 and p-CH 3) have been determined in various solvents and in buffers. It was found that the structure is dominated by the formation of intramolecular hydrogen bonding between the hydroxyl and the carbonyl groups rather than that between the hydroxyl and imino groups. For (a). an additional hydrogen bond occurs between the imino hydrogen and the chlorine in the 2′-position. Intramolecular charge transfer occurs through the non-bonding electrons on the imino group as donor, rather than through the aniline group, and the carbonyl group as acceptor. In strongly polar solvents, the enol structure occurs.
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