(E)-4-(((2-Amino-5-chlorophenyl)imino)methyl)-5-(hydroxy-methyl)-2-methylpyridin-3-ol and its Cu(II) complex: Synthesis, DFT calculations and AIM analysis

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Published: Aug 25, 2020
DOI: https://doi.org/10.2298/JSC191010022Y
Keywords:
Schiff base pyridoxal DFT copper(II) AIM tautomerization

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Morteza Yavari
Department of Chemistry, Mashhad Branch, Islamic Azad University, Mashhad
S. Ali Beyramabadi
Department of Chemistry, Mashhad Branch, Islamic Azad University, Mashhad
http://orcid.org/0000-0001-9616-8550
Ali Morsali
Department of Chemistry, Mashhad Branch, Islamic Azad University, Mashhad
Mohammad Reza Bozorgmehr
Department of Chemistry, Mashhad Branch, Islamic Azad University, Mashhad

Abstract

Herein, (E)-4-{[(2-amino-5-chlorophenyl)imino]methyl}-5-(hydro­xymethyl)-2-methylpyridin-3-ol [HL] Schiff base and its [Cu(L)Cl] complex were newly synthesized and characterized by several spectroscopic methods. In addition, density functional theory (DFT) methods were used for investigation of the tautomerization of the HL Schiff base, structural parameters of HL and [Cu(L)Cl] species, assignment of the IR vibrational bands and the NMR chem­ical shifts as well as natural bond orbital (NBO) analyses. The most stable tau­tomer of the HL Schiff base is the enol form of the meta isomer. The opti­mized geometry of the free HL Schiff base is not planar. The L- acts as a N2O tridentate ligand, which is bonded to Cu2+ via the deprotonated phenolic oxy­gen, and the amine and azomethine nitrogens. The [Cu(L)Cl] has a square pla­nar geometry in which the chloro ligand occupies the fourth coordination posit­ion. The DFT-computed values are in good consistency with the corresponding experimental values, confirming the suitability of the optimized geometries for HL and [Cu(L)Cl] species. According to the high-energy gaps, these com­pounds are stable. The atoms in molecule (AIM) analysis was used to evaluate strength of the bonding interactions and electron densities in structure of the compounds.

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[1]
M. Yavari, S. A. Beyramabadi, A. Morsali, and M. R. Bozorgmehr, “(E)-4-(((2-Amino-5-chlorophenyl)imino)methyl)-5-(hydroxy-methyl)-2-methylpyridin-3-ol and its Cu(II) complex: Synthesis, DFT calculations and AIM analysis”, J. Serb. Chem. Soc., vol. 85, no. 8, pp. 1033–1046, Aug. 2020.
Issue
Vol. 85 No. 8 (2020)
Section
Theoretical Chemistry

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