Synthesis, characterization, and in vitro antimicrobial activity of organotin(IV) complexes with triazolo-pyrimidine ligands containing exocyclic oxygen atoms.

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Abstract

Tri-organotin(IV) complexes of the triazolo-pyrimidine derivatives 4,5-dihydro-5-oxo-[1,2,4]triazolo-[1,5a]pyrimidine (5HtpO),4,7-dihydro-5-methyl-7-oxo-[1,2,4]triazolo-[1,5a]pyrimidine (HmtpO), and 4,5,6,7-tetrahydro-5,7-dioxo-[1,2,4]triazolo-[1,5a]pyrimidine(H2tpO2), and the diorganotin derivative n-Bu2Sn(tpO2), were synthesized and characterized by means of infrared and 119SnMo¨ssbauer spectroscopy. In all the complexes obtained the triazolopyrimidines act as multidentate ligands producing polymericstructures.A trigonal bipyramidal arrangement of the ligands around the tin atom is proposed for triorganotin(IV) derivatives, with organicgroups on the equatorial plane and bridging anionic ligands.DFT calculations were performed on the structure of H2tpO2 and on its mono- an di-anions, to investigate their harmonic vibrationalmodes. The observed trend of the experimental and calculated carbonyl stretching frequencies furnishes a support for theinterpretation of the structure of the organotin(IV) complexes obtained with this ligand.The structure of n-Bu2Sn(tpO2) was elucidated by quantum chemical calculations, performed on a model system of the polymericcomplex by a two layers ONIOM method. The combined experimental and theoretical results obtained support for a trans-n-Bu2distorted octahedral geometry, with the tpO2 2 units acting as bis-chelate ligands bridging the diorganotin(IV) moieties, and with theN(1)O(7) and N(4)O(5) chelating groups in the equatorial plane showing a cis-O2, or cis-N2, coordination.In vitro antimicrobial tests were performed on n-Bu3Sn(HtpO2) and Ph3Sn(HtpO2), and a good antifungal and antibiofilm activitywas observed, in particular for n-Bu3Sn(HtpO2).
Original languageEnglish
Pages (from-to)4773-4783
Number of pages11
JournalJournal of Organometallic Chemistry
Volume690
Publication statusPublished - 2005

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry
  • Materials Chemistry

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