Hydrogen bonding in phenol, aniline, and thiophenol by nuclear magnetic resonance spectroscopy and cryoscopy

Hydrogen bonding in phenol, aniline, and thiophenol has been investigated by n.m.r. spectroscopy and cryoscopy. While phenol shows evidence for the presence of monomer-dimmer-polymer equilibrium, thiophenol only indicates low monomer-dimer equilibrium. The extent of association in these three systems decreases in the order phenol, aniline, thiophenol