Ab initio calculations on the hydrogen bonding interactions among pseudoephedrinium cation isomers and methacrylic acid

Abstract

The hydrogen bonding interactions between both 1R-2R and 1S-2S isomers of pseudoephedrinium cation (Drug) and methacrylicacid (MAA) were calculated using Gaussian 98 software. Eight possible forms for the H-bond interactions were computed at HF and B3LYP levels of theory with 6-31G(d) and 6-31+G(d,p) basis sets and for all of the molecules the B3LYP/6-31G* provides the highest stabilization energies. The hydrogen bonding energies, E(H−bond), were obtained from the equation E(H−bond) = E(complex) - (E(Drug) + E(MAA)) and among four computational methods, B3LYP/6-31G(d) provides the highest hydrogen bonding energy for all of the complexes. The nuclear quadrupole coupling constants (�) for 17 O, tetrahedral 14 N nuclei were calculated about 10.0, 0.5-1.0 MHz and for 2 H atoms varied from nearly 150.0 kHz to almost 350.0 kHz.