Structural Analogues of Thyronamines. Experimental and DFT-Calculated 1H NMR Chemical Shifts of 4-[4-(2-Aminoethoxy)benzyl]aniline

Abstract

The structure and ¹H NMR chemical shifts of a new structural analogue of endogenous thyronamines, 4-[4-(2-aminoethoxy)benzyl]aniline, have been simulated in the framework of the density functional theory. The molecular geometry of the title compound has been optimized at the B3LYP level of theory using 6-31G(d,p), 6-31+G(d,p), and 6-311G(d,p) basis sets both for the isolated molecule and including solvent effect. The ¹H NMR chemical shifts of 4-[4-(2-aminoethoxy)benzyl]aniline have been estimated on the basis of magnetic shielding constants calculated by the GIAO method. In the calculations of both optimal molecular geometry and magnetic shielding constants, nonspecific solvation with dimethyl sulfoxide and methanol was considered in terms of the polarizable continuum model (IEFPCM). Linear correlations have been found between the theoretical and experimental chemical shifts of 4-[4-(2-aminoethoxy)benzyl]aniline in methanol-d₄ and DMSO-d₆.