Abstract
AbstractHydrogen bonding between N‐t‐butoxycarbonylproline N′‐methylamide and phenol derivatives (pKa = 10.20–7.75) are investigated by ir and Fourier transform ir spectrometry. The thermodynamic parameters determined in carbon tetrachloride solution show that the complexes are of medium strength, the stability constants at 298 K range from 80 to 1530 L mol−1, and the enthalpies of complex formation range from – 30 to –34 kJ mol−1. The study of the ir spectra in the νOH, νNH, and νco regions shows that complex formation occurs at the oxygen atom of the amide carbonyl. Hydrogen‐bond formation at this site strengthens the intramolecular hydrogen bond of the seven‐membered ring. © 1993 John Wiley & Sons, Inc.
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