Influence of chelate ligand structure on amide methanolysis reactivity of mononuclear zinc complexes

INOR 131

Gajendrasingh K. Ingle1, Magdalena M. Makowska-Grzyska1, Ewa Szajna-Fuller1, Sara Huefner1, John C. Price1, Atta M. Arif2, and Lisa M. Berreau, berreau@cc.usu.edu1. (1) Department of Chemistry and Biochemistry, Utah State University, 0300 Old Main Hill, Logan, UT 84322-0300, (2) Department of Chemistry, University of Utah, 315 S. 1400 E., Rm. 2020, Salt Lake City, UT 84112
Mononuclear zinc complex of N4O-, N3SO-, N2S2O-, and N2O-donor chelate ligands, with the oxygen donor being from an amide oxygen, have been prepared and comprehensively characterized. Each complex was treated with Me4NOH in CH3OH:CH3CN and the resulting products were characterized and quantified. Examination of the initial species generated immediately following the addition of Me4NOH revealed the production of deprotonated amide-containing zinc complexes for all chelate ligand types. For zinc complexes supported by thioether sulfur-containing chelate ligands, the presence of free chelate ligand is also identifiable in the reaction mixture prior to amide cleavage. Kinetic studies and proposed mechanistic pathways for the amide methanolysis reactions of these complexes will be presented.