Triphenyltin(IV) sulfanylpropenoates: synthesis, crystal structures and antimicrobial activities

Abstract

Three new triphenyltin(IV) sulfanylcarboxylates with the general formula [Q][SnPh 3 (L)] (Q = diisopropylammonium cation; L = tspa, pspa or pyspa, where t = 3-(2-thienyl)-, p = 3-(2-phenyl)-, py = 3-(2-pyridinyl)-and spa = 2-sulfanylpropenoato) have been prepared by reaction of triphenyltin(IV) hydroxide with the corresponding acid in the presence of di-isopropylamine in ethanol. The compounds have been characterized by elemental analysis and mass spectrometry and by IR, Mössbauer and NMR ( 1 H, 13 C, 119 Sn) spectroscopy. X-ray studies of the crystal structures of [Q][SnPh 3 (pspa)] and [Q][SnPh 3 (pyspa)] show that in both compoundsthe tin atom is coordinated to three phenyl C atoms and to S and one O atom of the ligand L. All three complexes are active against strains of the Gram-positive bacterium Staphylococcus aureus, but are inactive or only slightly active against the Gram-negative bacteria Escherichia coli and Pseudomonas aeruginosa.

Synthesis, structure and cytotoxicity of triphenylphosphinegold(I) sulfanylpropenoates

“…The Au-S and Au-P bond lengths, which are slightly longer in 7 AE 2/3C 3 H 6 O, are close to the values found in other compounds with an S-Au-P fragment [18,29]. The AuAEAEAEO (1) [20,21,31,32] and are close to the theoretical length of a single C-S bond, 1.81 Å [33]. Both the -Cl and -OCH 3 phenyl substituents are trans to the S atom in 5 and 6, respectively.…”

“…Assignment of the signals was based on HMQC and HMBC experiments and on previous data [20,31,32]. The broad signal at about 13 ppm in the 1 H NMR spectra of the ligands persists in the complexes, in keeping with the non-deprotonated nature of the CO 2 H group, and the shift of the C (3) [18,20,31,32]. This coordination mode is corroborated by the 13 …”

Synthesis, structure and cytotoxicity studies of diisopropylammonium and triethylammonium salts of triphenylphosphinegold(I) sulfanylcarboxylates

“…In 5 the carboxylate group is practically orthogonal to the plane in which the other donor atom, S, is located, a situation that makes the AuÁ Á ÁO interaction difficult. However, in this case the S-C(2)- [32] and is similar to the situation found for the Au complexes that contain this class of Hxspa ligand with the undeprotonated carboxylic acid group [18,21]. The values for the parameter Dm ¼ ½m as ðCO À 2 Þ À m sym ðCO À 2 Þ are 237 and 211 cm À1 , respectively, in the two complexes and in both cases these fall in the established range for monodentate carboxylate groups [33].…”

Synthesis and antimicrobial activities of gold(I) sulfanylcarboxylates

“…Remarkable activity was not exhibited by either diisopropylammonium chloride [42], the ligands or complexes of the type [Au(HL)] (1-11), which in the case of the complexes can be attributed to the low solubility.…”

“…The existence of the diisopropylammonium cation is confirmed by the presence, at around 1,600 cm −1 , of a band due to the NH 2 + group [41], which was previously identified in equivalent complexes with the same ligands [14,15]. The ν asym (CO 2 − ) and ν sym (CO 2 − ) bands are located in similar positions in the spectra of all the complexes, suggesting the same coordination mode for the carboxylate group, which, in all cases, acts as a monodentate group that is hydrogen bonded to the HQ cations [14,15,42] The IR spectra of Na[Au(L)]·H 2 O complexes do not contain the ν(SH) band or the bands due to the COOH group. The positions of the ν asym (CO 2 − ) and ν sym (CO 2 − ) bands are again similar in all of the complexes and these positions are again compatible with the same kind of monodentate coordination mode for the carboxylate group, which, in these cases, can be hydrogen bonded to the H 2 O molecule instead of the diisopropylammonium cation.…”