Organotin Polyamine Esters from Reaction of 6-Aminopenicillanic Acid and Organotin Dihalides.

CARRAHER JR., CHARLES E.; GUPTA, AMIT; RONER, MICHAEL R.

Polyamine esters have been formed from the classical interfacial polycondensation of 6- aminopenicillanic acid and organotin dihalides. Reaction is rapid occurring within 15 seconds. Product yield is moderate, 11-47%, with the products being low to moderate polymers, chain length of 37-1200. MALDI MS results show the presents of ion fragments to about 2kDa including ion fragment clusters up to four units in length. Bond scission occurs at the heteroatom sites on the polymer backbone. Infrared results are consistent with the formation of Sn-N and Sn-O(O)C linkages connecting the two moieties. Infrared spectroscopy is also consistent with the products having a mixture of N-Sn-N, N-Sn-O(O)C and C(O)-O-Sn-O-(O)C units about the tin with the geometry about the tin atom being a mixture of tetrahedral and octahedral, with the octahedral geometry the result of backbonding by the carbonyl oxygen. NMR shows the presence of both reactant moieties. The diethyltin and dibutyltin polymers exhibited favorable inhibition of two pancreatic cancer cell lines.

ORGANOTIN compounds; POLYAMINES; ESTERS; PENICILLANIC acids; HALIDES; DIBUTYLTIN; CARBONYL group

Journal of Polymer Materials, 2012, Vol 29, Issue 4, p387

0973-8622

Academic Journal