Metal induced cleavage of amide bonds. Part 3, Cleavage of aromatic amides and isolation of [cis-α-Co(trien) (salicylamide)](ClO4)2 (I), Co(tren)(pyrazine-2-carboxylato)](ClO4)2·2H2O (II) and [Co(tren)(pyrazine-2,3-dicarboxylatomonoamide)](ClO4)Cl (III)
Added Title
Cleavage of aromatic amides and isolation of [cis-α-Co(trien) (salicylamide)](ClO4)2 (I), Co(tren)(pyrazine-2-carboxylato)](ClO4)2·2H2O (II) and [Co(tren)(pyrazine-2,3-dicarboxylatomonoamide)](ClO4)Cl (III)
College
College of Science
Document Type
Article
Source Title
Inorganic Chimica Acta
Volume
362
First Page
4237
Last Page
4240
Publication Date
8-2009
Abstract
Three aromatic amides were allowed to interact with cis-[dichloro(N4)Co]+ cations in water solutions at controlled pH ranging from 7.0 to 7.5. N4 is a linear or a branched tetra-amine, such as trien or tren (trien = 1,4,7,10-tetraazadecane; tren = tris-(2-aminoethyl)amine). In one case(II), the effective result is displacement of the cis-dichloride ligands, amide hydrolysis and trapping of the generated carboxylate as a bidentate ligand to the cobalt amine fragment. In two others (I and III), the amide was trapped intact as a bidentate ligand to cobalt in which the NH2 fragment was dangling, unbound. These results are in line with previous studies carried out here on metal-induced amide and peptide hydrolyses. The products were isolated and characterized by NMR and X-ray diffraction. In all of our previous work the amides were aliphatic. We wanted to determine whether similar metal-induced hydrolytic cleavage would occur with aromatic amides. The answer is that the results depend on the conditions in which the reactions are carried out – details are given below. It is notable that in all three cases, some of the perchlorate oxygens are directly atop the π clouds of the aromatic rings, as discussed in the text. For example, in compound (III) three of the oxygens are over the π cloud at average distances of less than 3.5 Å.
html
Digitial Object Identifier (DOI)
https://doi.org/10.1016/j.ica.2009.05.034
Recommended Citation
Mukhapadhyay, U., Galian, R. F., & Bernal, I. (2009). Metal induced cleavage of amide bonds. Part 3, Cleavage of aromatic amides and isolation of [cis-α-Co(trien) (salicylamide)](ClO4)2 (I), Co(tren)(pyrazine-2-carboxylato)](ClO4)2·2H2O (II) and [Co(tren)(pyrazine-2,3-dicarboxylatomonoamide)](ClO4)Cl (III). Inorganic Chimica Acta, 362, 4237-4240. https://doi.org/https://doi.org/10.1016/j.ica.2009.05.034
Disciplines
Chemistry
Keywords
Scission (Chemistry); Amides; Diamonds; Nuclear magnetic resonance spectroscopy
Upload File
wf_no
