TY - JOUR
T1 - Synthesis, characterization, and in vitro antimicrobial activity of organotin(IV) complexes with triazolo-pyrimidine ligands containing exocyclic oxygen atoms.
AU - Girasolo, Maria Assunta
AU - Silvestri, Arturo
AU - Barone, Giampaolo
AU - Schillaci, Domenico
AU - Ruisi, Giuseppe
PY - 2005
Y1 - 2005
N2 - 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).
AB - 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).
KW - Antimicrobial activity
KW - DFT calculations
KW - Mossbauer
KW - Organotin(IV)
KW - Triazolopyrimidine
KW - Antimicrobial activity
KW - DFT calculations
KW - Mossbauer
KW - Organotin(IV)
KW - Triazolopyrimidine
UR - http://hdl.handle.net/10447/29691
M3 - Article
VL - 690
SP - 4773
EP - 4783
JO - Journal of Organometallic Chemistry
JF - Journal of Organometallic Chemistry
SN - 0022-328X
ER -