Trends in the oxygen-​hydrogen (O-​H)​..π interaction between proton donors and proton acceptors

The O[sbnd]H…π interaction between proton donor systems phenol, substituted phenols, benzyl alcohol and cyclohexanol and proton acceptor systems benzene, toluene, m- and p-xylenes, naphthalene and anthracene have been studied by infrared spectroscopy. It is found that the strength of the O[sbnd]H…π hydrogen bonding decreases in the following order: phenol > benzyl alcohol > cyclohexanol, and phenol > cresol> 2,6-dimethyl phenol > 2,4,6-tri-tret&utyl phenol. The strength of the proton acceptors, on the other hand, decreases in the fol lowing order: xylene > toluene > benzene > chlorobenzene, and for polyaromatic bases the trend is benzene > naphthalene > anthracene.