Amide bond cleavage initiated by coordination with transition metal ions and tuned by an auxiliary ligand.

Content Provider	Semantic Scholar
Author	Yang, Yongpo Lu, Chunxin Wang, Hailong Liu, Xiaoming
Copyright Year	2016
Abstract	The reaction of ligand , N,N-bis(pyridin-2-ylmethyl)acetamide, with five transition metal salts, FeCl3·6H2O, CuCl2·2H2O, Cu(ClO4)2·6H2O, ZnCl2 and K2PtCl4/KI, produced five metal complexes, [(μ-O)(FeClL')(FeCl3)] (), [CuLCl2] (), [CuBPA(ClO4)(CHCN)] ClO4 (), [ZnLCl2] () and [PtLI2] (), where = 1-(2,4,5-tri(pyridin-2-yl)-3-(pyridin-2-ylmethyl)imidazolidin-1-yl)ethanone which formed in situ, and BPA = bis(pyridin-2-ylmethyl)amine. The ligand and complexes were characterized by a variety of spectroscopic techniques including X-ray single crystal diffraction where applicable. Depending on the metal ion and auxiliary ligand of the complex, the acetyl group of the ligand could be either intact or cleaved. When ferric chloride hexahydrate was used, the deacetylation proceeded even further and a novel heterocyclic compound () was formed in situ. A possible mechanism was proposed for the formation of the heterocyclic compound found in complex . Our results indicate that to cleave effectively an amide bond, it is essential for a metal centre to bind to the amide bond and the metal centre is of sufficient Lewis acidity.
File Format	PDF HTM / HTML
DOI	10.1039/c6dt01411a
PubMed reference number	27241864
Journal	Medline
Volume Number	45
Issue Number	25
Alternate Webpage(s)	http://www.rsc.org/suppdata/c6/dt/c6dt01411a/c6dt01411a1.pdf
Journal	Dalton transactions
Language	English
Access Restriction	Open
Content Type	Text
Resource Type	Article