DFT Calculations on the hydrogen bonding interactions between adrenaline and trimethoxysilylpropylamine

SHARIATINIA, ZAHRA; ERBEN, MAURICIO FEDERICO; DELLA VÉDOVA, CARLOS OMAR

MAIN GROUP CHEMISTRY

TAYLOR & FRANCIS LTD

Lugar: Londres; Año: 2012 vol. 11 p. 275 - 284

1024-1221

The hydrogen bonding interactions between adrenaline (Drug) and -(trimethoxysilyl)-1-propanamine (TMSA) have been calculated using Gaussian 98 software. Ten possible forms (1–10) for the hydrogen bonding interactions were computed at HF and B3LYP levels of theory with 6-31 G(d) and 6-31 + G(d,p) standard basis sets. The binding energies,
E(binding), were obtained from the equation
E(binding) =E(complex) – [E(Drug) +E(TMSA)] + BSSE. The most stable forms (complexes 4 and 5) interact through O–H . . . N hydrogen bond, with calculated binding energies at B3LYP/6-31G* level equal to –10.93 and–12.84 kcal mol–1, respectively. Other compounds containing N–H···N (1), N–H···O (2, 3, 6, 9) and O–H . . . O (7, 8 and 10) hydrogen bonds showlower
E(binding) values. The nuclear quadrupole coupling constants (NQCCs or χs) were calculated for 17O, 14N and 2H nuclei about 10.0, 4.0–5.0MHz and 180.0–360.0 kHz, respectively, that are in agreement with the experimental data.