Hydrogen bond studies in substituted N-(2-hydroxyphenyl)--2-[(4-methylbenzenesulfonyl)amino]acetamides

Six substituted N-(2-hydroxyphenyl)-2-[(4-methylbenzensulfonyl)amino]acetamides 7-12 have been synthesized from 2-amino-3-nitrophenol, 2-amino-4-nitrophenol, 2-amino-5-nitrophenol, 2-amino-4-chlorophenol, 2-amino-4-tert-butylphenol, 2-amino-4-chloro-5-nitrophenol, and the [(4-methylbenzenesulfonyl)amino]acetyl chloride derivative of [(4-methylbenzenesulfonyl)amino]acetic acid. These compounds have been characterized by FAB mass spectrometry, IR, and NMR (1H, 13C, 15N) spectroscopy. Variable temperature NMR experiments on compounds 7-12 gave evidence for the formation of intra- and intermolecular hydrogen-bonds in solution. The molecular structure of 7 and 12 was determined by X-ray crystallography. The electronic behavior of the intramolecular hydrogen-bonds in these compounds was established by NBO studies.