Synthesis and spectroscopic studies of organotin compounds containing the Sn_S bond (original) (raw)
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Synthesis and spectroscopic studies of some organotin(IV) compounds containing the SnO bond
Journal of Inorganic and Nuclear Chemistry, 1979
The preparation of a number of organotin(IV) compounds, containing Sn-O bonds, is described. Their ~3C and rH NMR, IR spectra, and some molecular weight determinations, are presented. Structures are postulated based largely on the one bond coupling constant ~J('9/H7SnJ3C). Further evidence is obtained from ~H NMR and IR spectra. For the compounds reported, IR spectra do not appear to provide unambiguous evidence because of difficulties in assigning and interpreting C=O, Sn-O and Sn-C stretch frequencies.
Applied Organometallic Chemistry, 2001
The reactions of dimethyltin dichloride with nitrogen and sulfur donor ligands derived by condensation of S-benzyldithiocarbazate with indol-3-carboxylaldehyde, thiophene-2-aldehyde and furfuraldehyde have been investigated in 1:1 and 1:2 molar ratios in anhydrous alcohol. These ligands act as mononegatively charged bidentate species and coordinate to the central tin(IV) atom through the thiosulfur by proton exchange with the azomethine nitrogen. The newly synthesized complexes have been characterized by elemental analysis, conductance measurements and molecular weight determinations. The mode of bonding and the geometry of the complexes have been suggested on the basis of infrared, electronic and 1H, 13C and 119Sn NMR spectroscopy, and probable structures have been assigned to these complexes. A few representative ligands and their tin(IV) complexes have also been screened for their antifungal and antibacterial activities and found to be quite active in this respect. Copyright © 2001 John Wiley & Sons, Ltd.
Synthesis and characterization of new organotin(IV) complexes with polyfunctional ligands
Journal of Organometallic Chemistry, 2006
New mono-, di-and tri-organotin(IV) derivatives containing the neutral bis(2-pyridylthio)methane ligand, [(pyS) 2 CH 2 ] and tris(2-pyridylthio)methane ligand, [(pyS) 3 CH] have been synthesized from reaction with SnR n Cl 4Àn (R = Me, n Bu, Ph and Cy, n = 1-3) acceptors. Mono-nuclear adducts of the type {[(pyS) 2 CH 2 ]R n SnCl 4Àn } and {[(pyS) 3 CH]R n SnCl 4Àn } have been obtained and characterized by elemental analyses, FT-IR, ESI-MS, multinuclear ( 1 H and 119 Sn) NMR spectral data. The 1 H and 119 Sn NMR and ESI-MS data suggest for the triorganotin(IV) derivatives a complete dissociation of the compounds in solution. The mono-and di-organotin(IV) derivatives show a greater stability in solution, and their spectroscopic data are in accordance with the existence of six-coordinated RSnCl 3 N 2 or R 2 SnCl 2 N 2 species.
Bioinorganic Chemistry and Applications, 2006
Three bidentate Schiff bases having nitrogen and sulphur donor sequences were prepared by condensing S-benzyldithiocarbazate (NH 2 NHCS 2 CH 2 C 6 H 5 ) with heterocyclic aldehydes. The reaction of diphenyltin dichloride with Schiff bases leads to the formation of a new series of organotin(IV) complexes. An attempt has been made to prove their structures on the basis of elemental analyses, conductance measurements, molecular weights determinations, UV, infrared, and multinuclear magnetic resonance ( 1 H, 13 C, and 119 Sn) spectral studies. Organotin(IV) complexes were five-and six-coordinate. Schiff bases and their corresponding organotin complexes have also been screened for their antibacterial and antifungal activities and found to be quite active in this respect.
Synthesis and Applications of Organotin(IV) Compounds: Mini Review
Journal of Sustainable Materials Processing and Management
Organotin(IV) compounds have seen a marked increase in industry utilization over the years and exhibited enormous economic benefits as well as environmental costs due to their numerous industrial, medical, and agricultural uses and other applications. The present review is a continuation of aseries of reviews on the use of organotin(IV), chemicals, synthesis, characteristics and geometry as well as the industrial and biological applications.
Journal of Organometallic Chemistry, 2014
In 1849, attempts to isolate free alkyl groups led to discovery of an organostannane, (C 2 H 5) 2 SnI 2 , which was analyzed in 1852. Coevally, aims at extension of trialkylstibine and trialkyl bismuth chemistry yielded [(C 2 H 5) 2 Sn] n , finally consisting rather of (cyclic) oligostannanes than polystannanes; the latter might have been degraded to the former though. Further, those reports described conversion of (C 2 H 5) 2 SnI 2 or [(C 2 H 5) 2 Sn] n to (C 2 H 5) 2 SnO, in fact a polymer, [(C 2 H 5) 2 SnO] n. These three substances were employed as starting materials for exploration of new alkylstannanes, and moreover some of the compounds thus obtained were used for synthesis of other organostannanes. Thus, e.g., dialkylstannanes (C 2 H 5) 2 SnX 2 (X ¼ Br, Cl, nitrate, formate, acetate) and a number of corresponding methyl derivatives were prepared, as well as (C 2 H 5) 2 SnSO 4 , (CH 3) 2 SnSO 4 , (C 2 H 5) 2 Sn(C 2 O 4) and tetraalkylstannanes. Dinuclear tin compounds were also addressed, in particular (C 2 H 5) 3 SneSn(C 2 H 5) 3 , (C 2 H 5) 2 ISneSn(C 2 H 5) 2 I, and (C 2 H 5) 3 SnOSn(C 2 H 5) 3. The latter arose as a reversibly formed dehydration product of (C 2 H 5) 3 SnOH. This hydroxide and (CH 3) 3 SnOH served for the synthesis of trialkylstannanes R 3 SnX (R ¼ ethyl: X ¼ Br, Cl; R ¼ ethyl or methyl: X ¼ formate, acetate, butyrate), [(C 2 H 5) 3 Sn] 2 SO 4 , [(CH 3) 3 Sn] 2 SO 4 and [(C 2 H 5) 3 Sn] 2 (C 2 O 4). Among the synthesis routes substitution and addition reactions were applied, and even the so-called Kocheshkov redistribution reaction (Kocheshkov comproportionation) was already described, namely by Buckton who thus obtained (C 2 H 5) 3 SnCl. Hence, already by 1860 a diversity of organotin compounds and related reactions was established, and the base for methodical exploration of organotin compounds was laid. Ó 2013 Elsevier B.V. All rights reserved. 14.15 for nitrogen [4] (also called azote [1,5]), 16.09 for sulfur [4], 35.42 for chlorine [4] and 58.82 for tin (calculated from the value of 735.23 on the basis of 100 for oxygen) [6]. Since a number of chemists were of the opinion that all relative atomic masses must be multiples by whole numbers of the atomic mass of hydrogen [4,7], rounded values were also common [4,8] (e.g.
Review of organotin compounds: chemistry and applications
Organotin compounds find a bigger range of technological and industrial applications than the organic compounds of any other metal. Many of these applications involve catalysis or anticatalysis, often in polymer chemistry, and they have an importance out of all proportion to the tonnage of tin which is used. This article reviews the present standing of the non-biological applications of organostannanes, with an emphasis on the mechanisms of the reactions which are involved. The three major families of organometallic compounds which find application in technology and industry are those based on aluminium, silicon, and tin. Alkylaluminium compounds are highly reactive, and their applications depend on their chemical properties as alkylating agents, for example towards tin tetrachloride in the production of alkyltin compounds. Organotin compounds were first studied in 1852 by Löwig, who prepared diethyltin by the action of a sodium-tin alloy upon ethyl iodide. In the following year Frankland prepared tetraethyltin and in the next years a considerable number of both alkyl and aryl organotin compounds were synthesized and described. In the course of these studies more than one of the investigators became aware of the poisonous nature of some of these compounds and Frankland himself was made ill for several months, but happily recovered, and there are no reports that any of those affected actually succumbed. It was evident that certain organotin compounds, notably triethyltin hydroxide and triethyltin acetate, were highly toxic; this was confirmed in 1881 by White, who studied their effects upon dogs and other animals. A period of 70 years was to elapse before the significance of these preliminary observations was realized.