The heterocyclic ligands [1,2,4]triazolo-[1,5-a]pyrimidine (tp) and 5,7-dimethyl-[1,2,4]triazolo-[1,5-a]pyrimidine (dmtp), react with diorganotin dichlorides giving the addition compounds Me2SnCl2(tp)2, Et2 SnCl2(tp)2, Me2 SnCl2(dmtp)2, Et2 SnCl2(dmtp)2, Bu2SnCl2(dmtp), Ph2SnCl2(dmtp). The organotin:ligand stoichiometry goes from 1:2 to 1:1 by increasing the steric hindrance of the organic groups bound to tin. The compounds have been characterized by means of infrared, 119Sn Mo¨ssbauer and 1H AND 13C NMR spectroscopy. The ligands presumably coordinate to tin classically through the nitrogen atom at the position 3. The 1:1 complexes adopt trigonal bipyramidal structures, with the organic groups on the equatorial plane and the ligand in the apical position. All-trans octahedral structures are inferred for the 1:2 complexes, except for Et2SnCl2(tp)2, characterized by a skew-trapezoidal structure. 119Sn Mo¨ssbauer measurements, at room temperature, in concomitance with DFT calculations, performed on isomeric structures of R2SnCl2(tp)2 (R = Me, Et), allowed us to conclude that the all-trans octahedral coordination induces self-assembly in the solid state, possibly accomplished through p–p stacking interactions among the planar ligands coordinated to the organotin(IV) compound, while the skew-trapezoidal structure attributed to Et2SnCl2(tp)2, induces the formation of monomeric adducts in the solid state. In vitro antimicrobial tests showed that [n-Bu2SnCl2(dmtp)] has interesting properties as anti Gram-positive and antibiofilm agent.

GIRASOLO, M.A., SCHILLACI, D., DI SALVO, C., BARONE, G., SILVESTRI, A., & RUISI, G. (2006). Synthesis, spectroscopic characterization and in vitro antimicrobial activity of diorganotin(IV) dichloride adducts with [1,2,4]triazolo-[1,5-a]pyrimidine and 5,7-dimethyl-[1,2,4]triazolo-[1,5,a]pyrimidine. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 691, 693-701 [10.1016/j.jorganchem.2005.10.007].

Synthesis, spectroscopic characterization and in vitro antimicrobial activity of diorganotin(IV) dichloride adducts with [1,2,4]triazolo-[1,5-a]pyrimidine and 5,7-dimethyl-[1,2,4]triazolo-[1,5,a]pyrimidine.

GIRASOLO, Maria Assunta;SCHILLACI, Domenico;BARONE, Giampaolo;SILVESTRI, Arturo;RUISI, Giuseppe
2006

Abstract

The heterocyclic ligands [1,2,4]triazolo-[1,5-a]pyrimidine (tp) and 5,7-dimethyl-[1,2,4]triazolo-[1,5-a]pyrimidine (dmtp), react with diorganotin dichlorides giving the addition compounds Me2SnCl2(tp)2, Et2 SnCl2(tp)2, Me2 SnCl2(dmtp)2, Et2 SnCl2(dmtp)2, Bu2SnCl2(dmtp), Ph2SnCl2(dmtp). The organotin:ligand stoichiometry goes from 1:2 to 1:1 by increasing the steric hindrance of the organic groups bound to tin. The compounds have been characterized by means of infrared, 119Sn Mo¨ssbauer and 1H AND 13C NMR spectroscopy. The ligands presumably coordinate to tin classically through the nitrogen atom at the position 3. The 1:1 complexes adopt trigonal bipyramidal structures, with the organic groups on the equatorial plane and the ligand in the apical position. All-trans octahedral structures are inferred for the 1:2 complexes, except for Et2SnCl2(tp)2, characterized by a skew-trapezoidal structure. 119Sn Mo¨ssbauer measurements, at room temperature, in concomitance with DFT calculations, performed on isomeric structures of R2SnCl2(tp)2 (R = Me, Et), allowed us to conclude that the all-trans octahedral coordination induces self-assembly in the solid state, possibly accomplished through p–p stacking interactions among the planar ligands coordinated to the organotin(IV) compound, while the skew-trapezoidal structure attributed to Et2SnCl2(tp)2, induces the formation of monomeric adducts in the solid state. In vitro antimicrobial tests showed that [n-Bu2SnCl2(dmtp)] has interesting properties as anti Gram-positive and antibiofilm agent.
GIRASOLO, M.A., SCHILLACI, D., DI SALVO, C., BARONE, G., SILVESTRI, A., & RUISI, G. (2006). Synthesis, spectroscopic characterization and in vitro antimicrobial activity of diorganotin(IV) dichloride adducts with [1,2,4]triazolo-[1,5-a]pyrimidine and 5,7-dimethyl-[1,2,4]triazolo-[1,5,a]pyrimidine. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 691, 693-701 [10.1016/j.jorganchem.2005.10.007].
File in questo prodotto:
File Dimensione Formato  
JOC2006.pdf

accesso aperto

Dimensione 252.7 kB
Formato Adobe PDF
252.7 kB Adobe PDF Visualizza/Apri

I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.

Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/10447/34394
Citazioni
  • ???jsp.display-item.citation.pmc??? ND
  • Scopus 30
  • ???jsp.display-item.citation.isi??? 30
social impact