Synthesis, Characterization and Computational Studies of (E)-2-{[(2-Aminopyridin-3-Yl) Imino]-Methyl}-4,6-Di-Tert-Butylphenol

Abstract

Aminopyridin-3-yl)imino]-methyl}-4,6-di-tert-butyl-phenol (3), a ligand containing an intramolecular hydrogen bond, was prepared according to a previous literature report, with modifications, and was characterized by UV-vis, FTIR, 1 H-NMR, 13 C-NMR, HHCOSY, TOCSY and cyclic voltammetry. Computational analyses at the level of DFT and TD-DFT were performed to study its electronic and molecular structures. The results of these analyses elucidated the behaviors of the UV-vis and electrochemical data. Analysis of the transitions in the computed spectrum showed that the most important band is primarily composed of a HOMO→LUMO transition, designated as an intraligand (IL) charge transfer.

Spectral, theoretical characterization and antifungal properties of two phenol derivative Schiff bases with an intramolecular hydrogen bond

“…48 All the frequencies were positive which mean that the minimum was found. 22 With respect to reduction only the compound L1 showed no electrochemical reversible peak potentials, but an important irreversible reduction process at -1.78 V, which is attributed to an intramolecular reductive coupling of the azomethine group, which involves a self-protonation reaction. = anionic.…”

“…21,22 The reaction was stirred for 24 h at room temperature and then filtered, and the precipitate was washed with methanol and diethyl ether. 21,22 The reaction was stirred for 24 h at room temperature and then filtered, and the precipitate was washed with methanol and diethyl ether.…”

“…22 The synthesis of (E)- 2 In order to understand the electronic structures of (E)-2-{[(2-aminopyridin-3-yl)imino]-methyl}-4,6-di-tert-butyl-phenol (L1) and (E)-2-{[ (3-aminopyridin-4-yl)imino]-methyl}-4,6-di-tert-butylphenol (L2), we employed DFT calculations using the approaches explained above. 22 The synthesis of (E)- 2 In order to understand the electronic structures of (E)-2-{[(2-aminopyridin-3-yl)imino]-methyl}-4,6-di-tert-butyl-phenol (L1) and (E)-2-{[ (3-aminopyridin-4-yl)imino]-methyl}-4,6-di-tert-butylphenol (L2), we employed DFT calculations using the approaches explained above.…”

“…were described by Kleij et al 21,22 In this work, a complete study of their electronic properties to understand the role of the hydrogen bond on its biological activities and molecular properties was performed. 5 2.…”

Experimental and theoretical studies of the ancillary ligand (E)-2-((3-amino-pyridin-4-ylimino)-methyl)-4,6-di-tert-butylphenol in the rhenium(i) core

“…1,2 Since then, they have attracted much attention due to their appealing photophysical properties and their luminescence properties based on the Re I core, which are adjustable and might be optimized by the variation of the (N,N) ligand structure, or more subtly, by tuning the electronic nature of the ancillary ligand L. [3][4][5] Several conjugated chelating ligands, such as diimine, indole and benzimidazoles, were attached to the fac-Re(CO) 3 + core showing therapeutic properties. 7,8 In addition, Gust et al 9 reported a benzimidazole substituent for bioinspired compounds that present an intramolecular hydrogen bond as dyes in sensitized solar cells. 7,8 In addition, Gust et al 9 reported a benzimidazole substituent for bioinspired compounds that present an intramolecular hydrogen bond as dyes in sensitized solar cells.…”