Spectroscopic studies of solvent effects on intramolecular hydrogen bonding in N-substituted salicylamides.
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It has been found from absorption and emission spectra that the intramolecular hydrogen bonds between the phenolic hydroxyl and carbonyl group of <I>N</I>-methylsalicylamide and <I>N</I>-methyl-5-chlorosalicylamide survive in DMSO as well as in 1,2-dichloroethane, whereas those of <I>N</I>,<I>N</I>-dimethylsalicylamide and <I>N</I>,<I>N</I>-dimethyl-5-chlorosalicylamide are disrupted in DMSO. The solvent dependence of the <SUP>1</SUP>H and <SUP>13</SUP>C chemical shifts of these compounds are also well related to the intramolecular hydrogen bonding.
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