PREDICTION OF HYDROGEN-BOND BASICITY IN NITRILES FROM DIPOLE-MOMENTS,MESOMERIC EFFECTS AND ELECTROSTATIC POTENTIALS

Measured molecular dipole moments and theoretical percentages of mesom eric zwitterionic forms were used to calculate the attractive electros tatic potentials at short, V(s), medium, V(m), and long, V(l), distanc es, Values of an attraction power function Phi (H) = A + BV(s)V(m)V(l) was then deduced for 18 nitriles and cyanamide vinylogues or iminolog ues along the C = N direction. The satisfactory agreement observed bet ween Phi (H) and the hydrogen bond basicity scale pK(HB) indicates tha t the method can be a useful tool for the prediction of hydrogen bondi ng, needing only simple calculations and allowing easy interpretation.