DFT investigation of the electronic structure of amphetamines: effect of substituent on O and N chemical shielding and electric field gradient tensors
by Zahra Fallah Ebrahimi; David J.D. Wilson
International Journal of Computational Biology and Drug Design (IJCBDD), Vol. 8, No. 4, 2015

Abstract: To understand the relationship between the electronic structure of amphetamines and their biological activity, a computational investigation was carried out to characterise the ¹⁷O and ¹⁴N, electric field gradient (EFG) tensors and nuclear quadrupole coupling constants (NQCC) as well as ¹⁷O, ¹⁵N, ¹³C and ¹H chemical shielding tensors of amphetamines. Calculation were performed with the B3LYP and PW91P86 density functional theory (DFT) methods with the 6-311++G(d,p) basis set. The anisotropic (Δσ) and isotropic (σ_iso) shielding are in good agreement with the available experimental data. The results indicate that the EFG and σ at oxygen are insensitive to substitution at the N and C₁₀ positions in amphetamines. In contrast, the nitrogen EFG and σ are quite sensitive towards substituent changes. Furthermore, it was found that EFG tensors are more sensitive than σ tensor to the electron density distribution in amphetamines. Biological activities of amphetamines were found to depend upon the electron density distribution in the region of N atoms.

Online publication date: Tue, 15-Dec-2015

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