Studies of hydrogen bonding: Part XXIX. An experimental and theoretical approach to the structure of nitriles and of hydrogen-bonded complexes with phenol

Dipole moments, μ_a, of four nitriles, have been determined experimentally and calculated by the CNDO/2 method. The results obtained can be accounted for in terms of a planar trimer parallel-antiparallel model held together in clusters. Experimental and CNDO/2 calculated dipole moments of hydrogen-bonded complexes between nitriles and phenol indicate strongly that the O-H proton in phenol is located perpendicular to the triple bond.