Prediction of hydrogen bond basicity in nitriles from dipole moments, mesomeric effects and electrostatic potentials
Author(s) -
Herail Martine,
Berthelot Michel,
Proutiere Alain
Publication year - 1995
Publication title -
journal of physical organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.325
H-Index - 66
eISSN - 1099-1395
pISSN - 0894-3230
DOI - 10.1002/poc.610080606
Subject(s) - chemistry , dipole , cyanamide , hydrogen bond , computational chemistry , bond dipole moment , molecule , transition dipole moment , organic chemistry
Abstract Measured molecular dipole moments and theoretical percentages of mesomeric zwitterionic forms were used to calculate the attractive electrostatic potentials at short, V (s), medium, V (m), and long, V (I), distances. Values of an attraction power function Φ ( H ) = A + BV (s) V (m) V (I) was then deduced for 18 nitriles and cyanamide vinylogues or iminologues along the C≡N direction. The satisfactory agreement observed between Φ ( H ) and the hydrogen bond basicity scale p K HB indicates that the method can be a useful tool for the prediction of hydrogen bonding, needing only simple calculations and allowing easy interpretation.