Triorganotin(IV) derivatives of 7-amino-2-(methylthio)[1,2,4]triazolo [1,5-a]pyrimidine-6-carboxylic acid. Synthesis, spectroscopic characterization, in vitro antimicrobial activity and X-ray crystallography

Bartolomeo Megna, Loredana Canfora, Maria Assunta Girasolo, Giuseppe Ruisi, Giuseppe Bruno, Teresa F. Mastropietro, Eugenio A. Debbia, Archimede Rotondo

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Abstract

Triorganotin(IV) complexes of the 7-amino-2-(methylthio)[1,2,4]triazolo[1,5-a]pyrimidine-6-carboxylicacid (HL), Me3SnL(H2O), (1), [n-Bu3SnL]2(H2O), (2), Ph3SnL(MeOH), (3), were synthesized by reacting theamino acid with organotin(IV) hydroxides or oxides in refluxing methanol. The complexes have been characterizedby elemental analysis, 1H, 13C and 119Sn NMR, IR, Raman and 119Sn Mössbauer spectroscopictechniques. Single crystal X-ray diffraction data were obtained for compounds (2) and (3). Ph3SnL(MeOH)presents a trigonal bipyramidal structure with the organic groups on the equatorial plane and the axialpositions occupied by a ligand molecule, coordinated to tin through the carboxylate, and a solvent molecule,MeOH. A similar structure is proposed for Me3SnL(H2O) on the basis of analytical and spectroscopicdata. The tributyltin(IV) derivative, [n-Bu3SnL]2(H2O), is characterized by two different tin sites with similartbp geometry featured by butyl groups on the equatorial plane. Sn(1) and Sn(2) atoms are axiallybridged by a ligand molecule binding through the N(4) and the carboxylate group; the two coordinationspheres are saturated by another ligand molecule, binding the metal through the carboxylate group, and awater molecule, respectively. Antimicrobial tests on compounds 1 and 2 showed in vitro activity againstGram-positive bacteria.
Lingua originaleEnglish
pagine (da-a)546-551
Numero di pagine6
RivistaJournal of Organometallic Chemistry
Volume695
Stato di pubblicazionePublished - 2010

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X ray crystallography
X Ray Crystallography
pyrimidines
Carboxylic Acids
Carboxylic acids
carboxylic acids
crystallography
Tin
Ligands
Derivatives
Molecules
carboxylates
synthesis
Hydroxides
molecules
x rays
ligands
tin
X-Ray Diffraction
Oxides

All Science Journal Classification (ASJC) codes

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

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@article{d5e3284e706d4873baa5a6dd102d58bd,
title = "Triorganotin(IV) derivatives of 7-amino-2-(methylthio)[1,2,4]triazolo [1,5-a]pyrimidine-6-carboxylic acid. Synthesis, spectroscopic characterization, in vitro antimicrobial activity and X-ray crystallography",
abstract = "Triorganotin(IV) complexes of the 7-amino-2-(methylthio)[1,2,4]triazolo[1,5-a]pyrimidine-6-carboxylicacid (HL), Me3SnL(H2O), (1), [n-Bu3SnL]2(H2O), (2), Ph3SnL(MeOH), (3), were synthesized by reacting theamino acid with organotin(IV) hydroxides or oxides in refluxing methanol. The complexes have been characterizedby elemental analysis, 1H, 13C and 119Sn NMR, IR, Raman and 119Sn M{\"o}ssbauer spectroscopictechniques. Single crystal X-ray diffraction data were obtained for compounds (2) and (3). Ph3SnL(MeOH)presents a trigonal bipyramidal structure with the organic groups on the equatorial plane and the axialpositions occupied by a ligand molecule, coordinated to tin through the carboxylate, and a solvent molecule,MeOH. A similar structure is proposed for Me3SnL(H2O) on the basis of analytical and spectroscopicdata. The tributyltin(IV) derivative, [n-Bu3SnL]2(H2O), is characterized by two different tin sites with similartbp geometry featured by butyl groups on the equatorial plane. Sn(1) and Sn(2) atoms are axiallybridged by a ligand molecule binding through the N(4) and the carboxylate group; the two coordinationspheres are saturated by another ligand molecule, binding the metal through the carboxylate group, and awater molecule, respectively. Antimicrobial tests on compounds 1 and 2 showed in vitro activity againstGram-positive bacteria.",
keywords = "Crystal structure, Triazolopyrimidine, Triorganotin(IV) complexes, microRaman",
author = "Bartolomeo Megna and Loredana Canfora and Girasolo, {Maria Assunta} and Giuseppe Ruisi and Giuseppe Bruno and Mastropietro, {Teresa F.} and Debbia, {Eugenio A.} and Archimede Rotondo",
year = "2010",
language = "English",
volume = "695",
pages = "546--551",
journal = "Journal of Organometallic Chemistry",
issn = "0022-328X",
publisher = "Elsevier",

}

TY - JOUR

T1 - Triorganotin(IV) derivatives of 7-amino-2-(methylthio)[1,2,4]triazolo [1,5-a]pyrimidine-6-carboxylic acid. Synthesis, spectroscopic characterization, in vitro antimicrobial activity and X-ray crystallography

AU - Megna, Bartolomeo

AU - Canfora, Loredana

AU - Girasolo, Maria Assunta

AU - Ruisi, Giuseppe

AU - Bruno, Giuseppe

AU - Mastropietro, Teresa F.

AU - Debbia, Eugenio A.

AU - Rotondo, Archimede

PY - 2010

Y1 - 2010

N2 - Triorganotin(IV) complexes of the 7-amino-2-(methylthio)[1,2,4]triazolo[1,5-a]pyrimidine-6-carboxylicacid (HL), Me3SnL(H2O), (1), [n-Bu3SnL]2(H2O), (2), Ph3SnL(MeOH), (3), were synthesized by reacting theamino acid with organotin(IV) hydroxides or oxides in refluxing methanol. The complexes have been characterizedby elemental analysis, 1H, 13C and 119Sn NMR, IR, Raman and 119Sn Mössbauer spectroscopictechniques. Single crystal X-ray diffraction data were obtained for compounds (2) and (3). Ph3SnL(MeOH)presents a trigonal bipyramidal structure with the organic groups on the equatorial plane and the axialpositions occupied by a ligand molecule, coordinated to tin through the carboxylate, and a solvent molecule,MeOH. A similar structure is proposed for Me3SnL(H2O) on the basis of analytical and spectroscopicdata. The tributyltin(IV) derivative, [n-Bu3SnL]2(H2O), is characterized by two different tin sites with similartbp geometry featured by butyl groups on the equatorial plane. Sn(1) and Sn(2) atoms are axiallybridged by a ligand molecule binding through the N(4) and the carboxylate group; the two coordinationspheres are saturated by another ligand molecule, binding the metal through the carboxylate group, and awater molecule, respectively. Antimicrobial tests on compounds 1 and 2 showed in vitro activity againstGram-positive bacteria.

AB - Triorganotin(IV) complexes of the 7-amino-2-(methylthio)[1,2,4]triazolo[1,5-a]pyrimidine-6-carboxylicacid (HL), Me3SnL(H2O), (1), [n-Bu3SnL]2(H2O), (2), Ph3SnL(MeOH), (3), were synthesized by reacting theamino acid with organotin(IV) hydroxides or oxides in refluxing methanol. The complexes have been characterizedby elemental analysis, 1H, 13C and 119Sn NMR, IR, Raman and 119Sn Mössbauer spectroscopictechniques. Single crystal X-ray diffraction data were obtained for compounds (2) and (3). Ph3SnL(MeOH)presents a trigonal bipyramidal structure with the organic groups on the equatorial plane and the axialpositions occupied by a ligand molecule, coordinated to tin through the carboxylate, and a solvent molecule,MeOH. A similar structure is proposed for Me3SnL(H2O) on the basis of analytical and spectroscopicdata. The tributyltin(IV) derivative, [n-Bu3SnL]2(H2O), is characterized by two different tin sites with similartbp geometry featured by butyl groups on the equatorial plane. Sn(1) and Sn(2) atoms are axiallybridged by a ligand molecule binding through the N(4) and the carboxylate group; the two coordinationspheres are saturated by another ligand molecule, binding the metal through the carboxylate group, and awater molecule, respectively. Antimicrobial tests on compounds 1 and 2 showed in vitro activity againstGram-positive bacteria.

KW - Crystal structure

KW - Triazolopyrimidine

KW - Triorganotin(IV) complexes

KW - microRaman

UR - http://hdl.handle.net/10447/59665

UR - http://hdl.handle.net/10447/43753

M3 - Article

VL - 695

SP - 546

EP - 551

JO - Journal of Organometallic Chemistry

JF - Journal of Organometallic Chemistry

SN - 0022-328X

ER -