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Article

Ag(I) Complexes of Imine Derivatives of Unexpected 2-Thiophenemethylamine Homo-Coupling and Bis-(E)-N-(furan-2-ylmethyl)-1-(quinolin-2-yl)methanimine

1
School of Chemistry and Physics, University of Kwazulu-Natal, Pietermaritzburg Campus, Private Bag X01, Scottsville 3209, South Africa
2
Department of Chemical Sciences, Olabisi Onabanjo University, Ago-Iwoye, P. M. B. 2002, Ogun State 120107, Nigeria
3
School of Chemistry and Physics, University of Kwazulu-Natal, Westville Campus, Private Bag X54001, Westville 4001, South Africa
*
Author to whom correspondence should be addressed.
Academic Editor: Oleg A. Rakitin
Molbank 2021, 2021(2), M1235; https://doi.org/10.3390/M1235
Received: 14 May 2021 / Revised: 8 June 2021 / Accepted: 9 June 2021 / Published: 12 June 2021
(This article belongs to the Section Organic Synthesis)
Imines are fundamental organic compounds used as synthetic intermediates and as ligands in coordination chemistry. They are also found to be important pharmacophores in various bioactive compounds. In this report, two Schiff bases were prepared using the traditional condensation of 4-pyridinecarboxaldehyde with 2-thiophenemethylamine and 2-quinolinecarboxaldehyde with furfurylamine to form (E)-1-(pyridin-4-yl)-N-(thiophen-2-ylmethyl)methanimine (L1) and (E)-N-(furan-2-ylmethyl)-1-(quinolin-2-yl)methanimine (L2) respectively. L1 and L2 were complexed with silver perchlorate in 2:1 [M:L] stoichiometry to obtain complexes 1 and 2, respectively. The crystal structures of 1 and 2 were unequivocally determined by single-crystal X-ray diffraction analysis. The resulting structures revealed 2 to be a four-coordinate as expected. In contrast, an unexpected chemoselective hydrolytic cleavage of one mole of the (CH=N) imine ligands occurred in complex 2 and, further, the amines (thiophenemethylamine) homo-coupled to form a new imine ligand derivative in situ (L1a) before coordinating to the Ag(I) center along with L1. This observation described an alternative synthetic route to be explored to synthesize a diverse range of imine derivatives, which involves the Ag(I)-promoted homo-coupling of amines. Herein, the crystal structures of Ag(I) complexes of pyridinyl [Ag(L1)(L1a)]ClO4 (1) and quinolinyl [Ag(L2)2]ClO4 (2) Schiff bases are presented. View Full-Text
Keywords: Ag(I) complexes; thiophene; furan; pyridine; quinoline; homo-coupling amines; Schiff bases Ag(I) complexes; thiophene; furan; pyridine; quinoline; homo-coupling amines; Schiff bases
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MDPI and ACS Style

Adeleke, A.A.; Zamisa, S.J.; Omondi, B. Ag(I) Complexes of Imine Derivatives of Unexpected 2-Thiophenemethylamine Homo-Coupling and Bis-(E)-N-(furan-2-ylmethyl)-1-(quinolin-2-yl)methanimine. Molbank 2021, 2021, M1235. https://doi.org/10.3390/M1235

AMA Style

Adeleke AA, Zamisa SJ, Omondi B. Ag(I) Complexes of Imine Derivatives of Unexpected 2-Thiophenemethylamine Homo-Coupling and Bis-(E)-N-(furan-2-ylmethyl)-1-(quinolin-2-yl)methanimine. Molbank. 2021; 2021(2):M1235. https://doi.org/10.3390/M1235

Chicago/Turabian Style

Adeleke, Adesola A., Sizwe J. Zamisa, and Bernard Omondi. 2021. "Ag(I) Complexes of Imine Derivatives of Unexpected 2-Thiophenemethylamine Homo-Coupling and Bis-(E)-N-(furan-2-ylmethyl)-1-(quinolin-2-yl)methanimine" Molbank 2021, no. 2: M1235. https://doi.org/10.3390/M1235

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