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
| Autor: | Giampaolo Barone, Giuseppe Ruisi, Clelia Di Salvo, Domenico Schillaci, M. Assunta Girasolo, Arturo Silvestri |
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| Přispěvatelé: | GIRASOLO, MA, SCHILLACI, D, DI SALVO, C, BARONE, G, SILVESTRI, A, RUISI, G |
| Rok vydání: | 2006 |
| Předmět: |
Steric effects
Pyrimidine Ligand Stereochemistry Organic Chemistry DFT calculation chemistry.chemical_element Antimicrobial activity Biochemistry Medicinal chemistry Triazolopyrimidine Diorganotin(IV) Mossbauer DFT calculations Adduct Inorganic Chemistry Trigonal bipyramidal molecular geometry chemistry.chemical_compound chemistry Octahedron Mössbauer spectroscopy Materials Chemistry Physical and Theoretical Chemistry Tin |
| Zdroj: | Journal of Organometallic Chemistry. 691:693-701 |
| ISSN: | 0022-328X |
| DOI: | 10.1016/j.jorganchem.2005.10.007 |
| Popis: | 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, Et2SnCl2(tp)2, Me2SnCl2(dmtp)2, Et2SnCl2(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 Mossbauer 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 Mossbauer 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 π–π 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. |
| Databáze: | OpenAIRE |
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