35Cl-NQR and DFT study of electronic structure of amlodipine and felodipine vascular-selective drugs from the dihydropyridine Ca++ antagonists group

Amlodipine (AM) and felodipine (FL) have been studied in solid state by the nuclear quadrupole resonance (NQR) and density functional theory (DFT). The results have shown that NQR data do not permit a differentiation between R and S enantiomers, which is a consequence of the symmetry of the 4-aryl ring, whereas they permit a differentiation between free bases and salts. The HOMO–LUMO gap is smaller for AM than for FL, which suggests smaller energy of excitation for AM. The absolute hardness, chemical potential and electrophilicity of both AM enantiomers are lower than the corresponding values for FL enantiomers, suggesting that AM should be more reactive than FL in unimolecular reactions.