Structural analogues of thyronamines. Experimental and DFT calculated NMR 1H chemical shifts of 4-[4-(2-aminoethoxy)benzyl]aniline

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Abstract

The paper presents the results of molecular modeling of the structure and evaluation of the 1Н nuclei chemical shifts of a new structural analog of endogenous thyronamines, 4-[4-(2-aminoethoxy)benzyl]aniline. For 4-[4-(2-aminoethoxy)benzyl]aniline, the molecular geometry was optimized at the B3LYP level with basis sets 6-31G(d,p), 6-31+G(d,p), 6-311G(d, p) both in the approximation of an isolated molecule and with allowance for the solvent. The 1H nuclei chemical shifts of 4-[4-(2-aminoethoxy)benzyl]aniline were estimated on the base of the magnetic screening constants calculated by the GIAO method. The nonspecific solvation with dimethyl sulfoxide and methanol within the polarized continuum model (IEFPCM) was taken into account both in optimizing the molecular geometry and in calculating the magnetic screening constants. The calculated chemical shifts of the 1H nuclei for 4-[4-(2-aminoethoxy)benzyl]aniline are in good agreement with the experimental ones obtained in DMSO-d6 as well as CD3OD solutions. Linear correlations were obtained between the calculated and experimental data.

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A. B. Eresko

International Intergovernmental Organization “The Joint Institute for Nuclear Research”

Author for correspondence.
Email: a_eresko77@mail.ru
Russian Federation, ul. Joliot-Curie, 6, Dubna, 141980

E. V. Raksha

International Intergovernmental Organization “The Joint Institute for Nuclear Research”

Email: a_eresko77@mail.ru
ORCID iD: 0000-0002-5954-6361
Russian Federation, ul. Joliot-Curie, 6, Dubna, 141980

D. A. Filimonov

Federal State Budgetary Institution “V.K. Gusak Institute of Emergency and Reconstructive Surgery” of the Ministry of Health of the Russian Federation

Email: a_eresko77@mail.ru
ORCID iD: 0000-0002-4542-6860
Russian Federation, Leninskij ave, 47, Donetsk 283080

A. V. Muratov

Federal State Budget Scientific Institution “L.M. Litvinenko Institute of Physical Organic and Coal Chemistry”

Email: a_eresko77@mail.ru
Russian Federation, R. Luxemburg St, 70, Donetsk, 283114

A. A. Voitash

Federal State Budget Scientific Institution “L.M. Litvinenko Institute of Physical Organic and Coal Chemistry”

Email: a_eresko77@mail.ru
ORCID iD: 0000-0002-5441-3930
Russian Federation, R. Luxemburg St, 70, Donetsk, 283114

N. N. Trubnikova

Federal State Budgetary Institution “V.K. Gusak Institute of Emergency and Reconstructive Surgery” of the Ministry of Health of the Russian Federation

Email: a_eresko77@mail.ru
Russian Federation, Leninskij ave, 47, Donetsk 283080

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Supplementary files

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2. Fig. 1. The structure of endogenous thyronamines T0AM and T1AM, as well as their structural analogs – 4-[4-(2-aminoethoxy)benzyl]aniline (1) and 4-[4-(2-aminoethoxy)benzyl]phenol (2)

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3. Fig. 2. Atom numbering and 3D model of 4-[4-(2-aminoethoxy)benzyl]aniline (1) with the main structural fragments: aniline (a), oxybenzoic (b) and ethylamine (c)

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4. Fig. 3. 3D model of 4-[4-(2-aminoethoxy)benzyl]aniline (1) and visualization of frontier molecular orbitals (molecular geometry optimization was performed at the B3LYP/6-31G(d,p) level, bond lengths are given in Å)

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5. Fig. 4. Chemical shifts of 1H nuclei calculated for the 4-[4-(2-aminoethoxy)benzyl]aniline molecule (1) (□ – B3LYP/6-31G(d,p), ○ – B3LYP/6-31+G(d,p) and ▲ – B3LYP/6-311G(d,p)) and obtained experimentally in DMSO-d6 (a) and CD3OD [12] (b)

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