Date of Award
Master of Science
Dr. James A. Wisner
Isophthalamide and pyridine dicarboxamide have been a common motif to anion receptor design. Dynamic combinatorial chemistry has been a fast growing field towards the advancement of receptor design through the use of labile bonds. Schiff bases have been employed as the labile bonding unit of recent receptors.
A pyridine dicarboxamide analogue containing a labile bond via a semicarbazone unit was synthesized from the condensation between a semicarbazide and a pyruvamide. Two semicarbazone receptors displayed preferential binding of chloride over other common anions tested (Br‘, HSO4", TsO', AcCT, H2PO4 ). It was observed that chloride accelerates the formation o f the condensed semicarbazone receptor from 4- hexylsemicarbazide and phenylpyruvamide. Modifications to receptor design via the removal of a hydrogen bond donor site brought insight to the role that chloride plays in the mechanism of the condensation reaction. Other anions (HSO4’, TsO', Br\ T, CIO4', PFi", AcO") tested displayed acceleration in semicarbazone formation through hydrogen bonding.
Dan, Susanta, "Anion Accelerated Semicarbazone Formation with Pyruvamide" (2010). Digitized Theses. 3726.