Synthesis, spectroscopic characterization, and in vitro biological activity of organotin(IV) complexes of (E)‐3‐(4‐methoxyphenyl)‐2‐phenyl‐2‐propenoic acid

Abstract

Organotin(IV) complexes with general formula R4 − nSnLn have been synthesized by the reaction of tri‐ and diorganotin chlorides with sodium salt of (E)‐3‐(4‐methoxyphenyl)‐2‐phenyl‐2‐propenoic acid in dry toluene, where RCH3, C2H5, n‐C4H9, C6H5, n = 1 or 2, and L = [ŌOCC(C6H5) CH(C6H4OCH3)]. Dimeric distannoxanes, [(R2SnOOCC(C6H5)CH‐(C6H4OCH3)2O]2, were synthesized by the reaction of acid with diorganotin oxides in 1:1 molar ratio. Multinuclear NMR (1H, 13C, 119Sn), infrared, mass, and Mössbauer spectral techniques have been used to ascertain their structures in solution and as solid. The spectroscopic results showed that triorganotin(IV) derivatives are 4‐coordinated monomers in noncoordinating solvents and 5‐coordinated polymers with bridging carboxylate groups in the solid state. However, diorganotin and dimeric compounds are 5‐coordinated in noncoordinating solvents while in the solid phase may have higher coordination. Biological screening tests showed that most of the compounds have significant activity against different bacteria and fungi. © 2005 Wiley Periodicals, Inc. Heteroatom Chem 16:175–222, 2005; Published online in Wiley InterScience (http://www.interscience.wiley.com). DOI 10.1002/hc.20089

Organotin(IV) esters of (E)‐3‐furanyl‐2‐phenyl‐2‐propenoic acid: Synthesis, investigation of the coordination modes by IR, multinuclear NMR (1H, 13C, 119Sn) and In Vitro biological studies

“…In the spectrum of free ligand, single resonance is observed at 7.81 ppm, which appeared in the spectra of complexes in the region 7.69-7.89 ppm [14,[15][16][17]; see Table 3. Resonance signals for the protons of furanyl moiety of the ligand were assigned on the basis of 3 J [ 1 H, 1 H] values [26], while that of the phenyl moiety were assigned according to our earlier reports [14,[15][16][17]. The 2 J [ 119 Sn, 1 H] (81 and 57 Hz, respectively) values of dimethyltin(IV), 81 Hz (s, 1.04 ppm) and trimethyltin(IV), 57 Hz (s, 0.58 ppm) derivatives support the five-coordinated and four-coordinated environment around the tin atom in the solution [27].…”

“…moieties of the compounds, III-VI were assigned as described in the literature [19,[15][16][17]. Chemical shifts of the signals for the ligand moiety of all the investigated complexes appear almost at the same positions as in the free ligand acid (Table 3).…”

“…A slight upfield shift observed for C (1) of the compounds II and V could be due to the flow of charge from the electron with donating methyl (II) and n-butyl (V) groups to the tin, which in turn shifts electron density to the carbon C(1) of the electron with drawing carboxylic (COO) group [14,[15][16][17]. Here again the 13 C NMR assignments of organotin moieties of the synthesized complexes are based on those made previously [14,[15][16][17]; see Table 4. 119 Sn NMR chemical shifts of the complexes in CDCl 3 solution are listed in Table 4 [29].…”

“…As a part of our continuing program in this area [14][15][16][17] and based on the above-mentioned considerations, we have investigated a series of reactions of di-and triorganotin chlorides/oxides with (E)-3-furanyl-2-phenyl-2-propenoic acid. The generic structure of the ligand framework is shown in Fig.…”

Spectroscopic studies of biologically active organotin(IV) derivatives of 2-[N-(2,4,6-tribromophenylamido]propanoic acid

“…The triorganotin(IV) carboxylates are known to adopt a variety of motifs in the solid state, Figs. 2c-2e[13,14]. However, it is likely that the triorganotin(IV) species are linear polymers…”