Synthesis and structure of complexes of Co(II) acetate and Zn(II) chloride with 2-aminobenzothiazole

Kadirova, Shakhnoza; Tursunova, M. R.; Ishankhodzhaeva, M. M.; Парпиев, Н. А.; Karimov, Z.; Tozhiboev, A. G.; Ташходжаев, Б.

doi:10.1134/s1070363207100234

Cited by 7 publications

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“…The 2-aminobezothiazole ligand (abt) contains sulfur and nitrogen in a ring, an exocyclic nitrogen and π-electrons, giving the ligand a high coordination ability. Its coordination to the metal center via the nitrogen atom of the ring occurs in most of the reported crystal structures [27,28]. It is worth noting that the type of complexes have been widely studied as they exhibit interesting biological and photophysical properties [29][30][31].…”

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confidence: 99%

2-Aminobenzothiazole-Containing Copper(II) Complex as Catalyst in Click Chemistry: An Experimental and Theoretical Study

et al. 2020

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The reaction of copper(II) acetate with the 2-aminobenzothiazole (abt) heterocycle affords the new copper(II) complex of formula [Cu(abt)2(OOCCH3)2] (1) in a straightforward manner. Compound 1 served as a precatalyst for azide/alkyne cycloaddition reactions (CuAAC) in water, leading to 1,4-disubstituted-1,2,3-triazole derivatives in a regioselective manner and with excellent yields at room temperature. The main advantages of the coordination of such a heterocyclic ligand in 1 are its strong σ-donating ability (N-Cu), nontoxicity and biological properties. In addition, the click chemistry reaction conditions using 1 allow the formation of a great variety of 1,2,3-triazole-based heterocyclic compounds that make this protocol potentially relevant from biological and sustainable viewpoints. A molecular electron density theory (MEDT) study was performed by using density functional theory (DFT) calculations at the B3LYP/6-31G(d,p) (LANL2DZ for Cu) level to understand the observed regioselectivity in the CuAAC reaction. The intramolecular nature of this reaction accounts for the regioselective formation of the 1,4-regioisomeric triazole derivatives. The ionic nature of the starting copper-acetylide precludes any type of covalent interaction throughout the reaction, as supported by the electron localization function (ELF) topological analysis, reaffirming the zwitterionic-type (zw-type) mechanism of the copper(I)/aminobenzothiazole-catalysed azide-alkyne cycloaddition reactions.

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