Chelated compounds and derivative of β-alkoxycarbonylalkyltin chlorides — 5-arylazo-8-quinolinolates, alizarinates, and thiocyanate: preparation and spectroscopic studies

Abstract

Complex formation with chelating ligands like 5-phenylazo-8-quinolinol, 5-(21-carboxyphenylazo)-8-quinolinol, 1,2-dihydroxyanthraquinone (i.e., alizarin), and 1-nitroso-2-naphthol is due to nucleophilic attack on tin of the P-alkoxycarbonylalkyltin chlorides (a unique class of PVC stabilizer intermediates) with the subsequent elimination of h drogen chloride. A number of complexes of the types R2SnL2. RSnL2Cl, R2SnLCl, R2Sn(~'H')2, R2SnL1', and RSnLY'Cl (where R = CH30COCH2CH2-, C4H90COCH2CH2-, and CH30COCH(CH3)CH2-; LH = 5-phenylazo-8-quinolinol, l-nitroso-2-naphthol; L'HH' = 5-(21-carboxyphenylazo)-8-quinolinol; and LnH2 = 1,2-dihydroxyanthraquinone) and a thiocyanate derivative viz. (CH30COCH2CH2)2Sn(SCN)2 have been prepared. 5-Arylazo-8-quinolinols exhibit azo-hydrazone tautomeric equilibria but their complexes exist only in the azo form. P-Alkoxycarbonylethyltin alizarinates are somewhat different from other complexes. In these complexes two hydroxyl groups of alizarin have been utilised in complex formation, moreover, one of the two carbonyl groups of alizarin also remains involved in coordination to tin. In (CH30COCH2CH2)2Sn(SCN)2, the thiocyanate group is possibly linked to tin atom through nitrogen. All the complexes and the thiocyanate derivative have been characterised by elemental analyses, electronic, ir, and 'H nmr spectra. Possible structural features of the compounds are discussed.

Diphenyltin(IV) complexes of the 5-[(E)-2-(aryl)-1-diazenyl]quinolin-8-olates: Synthesis and multinuclear NMR, 119Sn Mössbauer, electrospray ionization MS, X-ray characterization and assessment of in vitro cytotoxicity

“…Ph 2 Sn(L 6 ) 2 (6) Orange crystals of 6 were obtained from a mixture of benzene and hexane (v/v 1:1 13 …”

“…Crystal data, data collection parameters and convergence results are listed in Table 1. For the tin complexes 1 AE (CH 3 ) 2 CO, 4 and 5, empirical absorption corrections based on a multiscan approach [15] or on azimuthal scans [16] were applied to the data sets before averaging over symmetry-related reflections; no absorption correction was made for the intensity data of Table 1 Crystal data, data collection parameters and convergence results for L 6 [17] and refined on reflection intensities F 2 using the SHELXL-97 program [18]. In the final least-squares refinements, all non-hydrogen atoms were refined with anisotropic displacement parameters, and hydrogen atoms were placed in idealized positions and included as riding on the corresponding atoms.…”

“…Consequently, some of the earlier publications have dealt with the coordinating behavior of such reagents towards organotin [4][5][6], transition metals [7], mixed organotintransition metals [7], mercury [8] and uranium [9]. Among the organotin(IV) compounds, bis{5-[(E)-2-(phenyl)-1-diazenyl]-8-quinolinolato}diphenyltin(IV), [Ph 2 Sn(L 1 ) 2 ] has been studied by IR, UV-Vis, 1 H NMR [5] and 119m Sn Mö ssbauer [4] 2 ], (where Ox = deprotonated quinolin-8-ol) [10] suggests that they have the same structure.…”

Synthesis and antimicrobial activities of sulfonohydrazide‐substituted 8‐hydroxyquinoline derivative and its oxinates

“…[14] Iron bound to the lipophilic chelator, 8HQ, causes substantial DNA strand breakage of cultured human lung cells. [15] 8-Hydroxyquinoline-like biological and pharmacological chelating agent-based ligands and chelates are in progress in coordination studies with increasing interest [16,17] and also in the field of metal extraction. [18] 8HQs exert the above-mentioned activities, possibly due to their ability to chelate with the metal ions, which essential for metabolism, [13] where the -OH group of 8HQ acts as an acid, dissociating to -O − .…”

Synthesis and electroreduction of 2-[(8-hydroxyquinoline-5-yl)azo]benzo[c]cinnoline in DMSO–H2O (1:1) medium

“…have already been reported to have antibacterial activities 19 and also suggested to be potential reagents for the trace analysis of some metals 20 . It would, of course, be desirable to incorporate some useful properties of benzo[c]cinnoline and its derivatives directing their use as dyes 21 , fiber intermediates 22 , charge-generating agents in electrophographic photoreceptors 23 and electrochromic polymers 24 into an azo dye.…”