Producción Científica Profesorado

The Effect of ZnII Coordination on the Addition of 2-(Aminomethyl)benzimidazole to Acrylonitrile



Galan Vidal, Carlos Andres

2014

The Effect of ZnII Coordination on the Addition of 2-(Aminomethyl)benzimidazole to Acrylonitrile, Martha P. Falcón-León, Antonio R. Tapia-Benavides, Hugo Tlahuext, Carlos Galán-Vidal, Oscar R. Suarez-Castillo, and Margarita Tlahuextl*, Eur. J. Inorg. Chem., 5415-5423 (2014), DOI:10.1002/ejic.201402346


Abstract


The effects of N[RIGHTWARDS ARROW]Zn coordination, solvent, and pH on the aza-addition reaction between 2-(aminomethyl)benzimidazole (HL) and acrylonitrile were studied. In the absence of ZnII ion, the aza-addition reactions between HL and acrylonitrile (in aqueous media) depended on pH and were not selective. The mono-addition compound {3-[(1H-benzimidazol-2-ylmethyl)amino]propanenitrile} was always obtained in a greater proportion than the di-addition products [3,3?-[(1H-benzimidazol-2-ylmethyl)imino]dipropanenitrile and 3-(2-{[(2-cyanoethyl)amino]methyl}-1H-benzimidazol-1-yl)propanenitrile]. Acrylonitrile selectively reacted at the amine group in the [ZnCl3(H2L)] and [ZnCl2(HL)] complexes in aqueous solutions. Moreover, [ZnCl(HL)2]Cl and [Zn(H2O)2(HL)2]Cl2 complexes yielded mixtures of mono- and di-addition products. In contrast, Zn complexes formed with HL did not react with acrylonitrile in solution in DMSO. The synthesis of mono- and di-addition compounds was studied by 1H and 13C NMR spectroscopy and X-ray diffraction crystallography. Quantum theory of atoms in molecules (QTAIM) computations were used to demonstrate the probable presence of a mono-addition chelate complex.



Producto de Investigación




Artículos relacionados

Electrochemical kinetic study about cobalt electrodeposition onto GCE and HOPG substrates from sulfa...

Kinetic study of the cobalt electrodeposition onto glassy carbon electrode from ammonium sulfate sol...

A theoretical quantum study on the distribution of electrophilic and nucleophilic active sites on Ag...

Quantum chemical study of the electrochemical reduction of the [Co(H2O)6]2+ and [Co(NH3)5(H2O)]2+ io...

Magnetic transition phase diagram of cobalt clusters electrodeposited on HOPG: Experimental and micr...

ELECTROCHEMICAL STUDY ABOUT ZINC ELECTRODEPOSITION ONTO GCE AND HOPG SUBSTRATES

Potentiometric behavior of graphite-epoxy electrochemical transducers towards anions, cations and pH...

Análisis del Comportamiento Presión-Temperatura en la Transición Isotrópico-Nemático del p-Azoxianis...

A theoretical quantum study on the distribution of electrophilic and nucleophilic active sites on th...

Nucleation and Growth Kinetics of Electrodeposited Sulfate-Doped Polypyrrole: Determination of the D...