Synthesis and Characterization of Tetraphenyltin

Synthesis and portrait of Tetraphenyl natesABSTRACTSTetraphenyltin in higher(prenominal) yield has been prep ared by the reply of chloro benzol, chlorotin (IV) and sodium metal in change methylbenzene characterized by Infra-red spectroscopy.IntroductionOrganic deepens that contains metal- ampere-second adhere are called organometallic compounds. Organometallic compounds have been examine for nearly two hundred years. Unique properties of these compounds have been utilize in many areas of life. The reactivity of organometallic compounds depends on the reduction potential of metal. For planning and exercise, it is markedly observed that nearly reactivity requires low to moderate temperature and inert conditions like atmosphere and solvent. mostly the reactivity of these compounds dealms like the ionic character of the carbon-metal bond, which may be estimated from the proton and carbon chemical shifts of methyl derivatives. % noodle character of H3CMetal as (CH3)2Hg 3) 2Cd 3)2Zn 3)2Mg 3L 1.The first inform organometallic compounds were prepared by the reductive substitution of alkyl group halides. Alkali metals have strong or moderate negative reduction potentials, with lithium and magnesium world the most reactive. Halide reactivity increases in the order Cl _R) tends to predominate. This post also be a puzzle when allyl or benzyl halides are converted to Grignard or lithium reagent 2.Organometallic compounds of group (IV) elementsThere is an highly extensive chemistry of the group quaternary elements bound to carbon and some of the compounds, notably silicon-oxygen polymers and alkyl tin and lead compounds are of commercial importance. Essentially all the compounds are of the type M(IV) type. In the divalent disk operating system the exactly well established compounds are cyclopentadienyl tin alkyls or aryls of formula R2Sn are either cursory or non-existent, and the stable substances of this stoichiometry are linear or cyclic polymers of tetravalent tin.For all the group four elements the compounds can generally be designated R4-nMXn where R is the alkyl or aryl and X can vary commodiously being H, Cl, O, COR, OR, NR2SR etc. For a make watern class of compounds those with C-Si and C-Ge bonds have higher thermal stability and land reactivity than those with bonds to Sn and Pb 3.Organometallic compounds of pottyThere are four series of organotin compounds depending on the deed of carbon-tin bonds. These series are designated as mono-, di-, tri-, and tetraorganotin compounds with the general formula RnSn X4-nWhereR = an alkyl or aryl groupSn = the central tin atom in the oxidation state +4X = a by the piece charged anion or an anionic organic group 4.Complexes of transition metalsThe ability of transition metals to form organo derivatives only begins to be appreciated properly during the nineteen fifties. Nonetheless, the organometallic compounds of transition metals now constitute an enormous, diversified fi eld of chemistry, which is gloss over expanding rapidly. It begins breadth by merging into the field of metal carbonyls and related compounds. They also differ in organise from that of non-transition organo-metal derivatives.The transition metals form compounds in which there is metal to carbon sigma bond although pi bond in some encases may also be formed. More important, the unique characteristic of d orbital abandon certain type of unsaturated hydrocarbons and some of their derivatives to be bound to metals in a non-classical manner to give molecules or ions with structures that have no counterpart elsewhere in chemistry. Not only is a wide order of organo compounds of different types are isolable, but also labile species play an important role in olefins, acetylene and their derivatives catalyzed by metal complexes 5.Applications of Organotin compoundsDepending on the organic groups, they can be powerful bactericides and fungicides 4.Tributyltins are used as industrial bioc ides, eg. as antifungal agents in textiles and paper, wood pulp and paper mill systems, breweries, and industrial cooling systems. Tributyltins are also used in marine anti-fouling paint 1.Triphenyltins are used as active components of anti fungal paints and agricultural fungicides 5.Organotin compounds are widely studied class of meta-based antitumor drugs 2.Organotin compounds are used in treatment of hyperbilirubinaemia 2.Organotin compounds are used in chemicals used for wood preservation 1. admission of Organotin compounds to PVC increases its stability 1.Organo metallic transition complexes also have role in molecular rearrangement processes 2.Hypercoordinated StannanesTin compounds can also be coordinated to five atoms instead of the regular four unlike their carbon analogues. The stability of these hypercoordinated compounds is managed by electronegative substituent. In 2007 a stable organotin (all carbon pentaorganostannane) was account at room-temperature (in argon) 4 in the form of lithium salt with the following structure.The geometry of the molecule is distorted trigonal bipyramidal. The carbon to tin bond lengths are 2.26 apical, 2.17 equatorial. These are larger than regular CSn bonds (2.14) which shows its hypervalent nature.Biological AspectsThe chemistry of the organotin(IV) derivatives is being theater of operations of study with growing interest, not only because of the environmental consequences of the widespread use of these compounds, but also as due to the increasingly importance of their medical assays for bactericide and antitumor purposes. In this respect, various triorganotins have been reported recently to be effective against mosquito larvae and adult mosquitoes responsible for malaria and yellow fever, and also some phenyltin derivatives display cardiovascular activity. In general, the structure-activity relationship in this kind of compounds is still subject of controversy, but it seems been established that, for instance, in the case of triorganotin carboxylates, those containing trans-O2SnC3 moieties exhibit a greater biocidal activity than those containing cis-O2SnC3.Organotin compounds have been implicated as reproductive toxicants and endocrinal disruptors to begin with by means of studies in aquatic organisms, with little information easy in mammals. Among the organotins, aryltins have been less studied than alkyltins. Extensive data is available on mammal developmental and reproductive perniciousness of one aryltin compound, triphenyltin (TPT), from perniciousness studies conducted in connection with the registration of triphenyltin hydrated oxide (TPTH) as a pesticide and supporting publications from the open literature. Indications of adverse operable and morphological effects on the reproductive tract of rats were reported in a dose range of 1.4-20 mg/kg/d. Gonadal histopathology (both ovaries and testes) and infertility were affected at the higher doses, while reproductive-tract cancer , teeny-weenyer set sizes, and reproductive organ weights were affected at the trim end of the dose range. In vitro studies indicate the TPT can directly activate androgen receptor-mediated transcription and inhibit enzymes that are involved in steroid endocrine metabolism. These data suggest that the aryltin TPT can be active as a reproductive toxicant in mammals and may be a human endocrine disruptor.Organotins are one of the classes of compounds implicated as endocrine disruptors (Colborn Clement, 1992) primarily on the basis of the finding of imposex in aquatic gastropods (Smith, 1981 Horiguchi et al., 1994). In these organisms, genetic fe anthropoids and parts of the male reproductive system, including the penis and vas deferens, superimposed on a normal female genital system. Implications for mammalian reproduction are less explored. There are no available epidemiological studies of the reproductive toxicity of organotins in humans or mammalian wildlife commonwealths, so that mammalian reproductive toxicity information is expressage to laboratory animals.Among the organotins, a particularly large database on reproductive toxicity in laboratory animals is available through studies conducted for registration of triphenyltin hydroxide as a pesticide. Triphenyltin (TPT) came into use as a fungicide and matricide in the 1950s (HSDB, 1998). Currently, about 10 products containing TPT are registered for use as pesticides by the U.S. Environmental Protection place (U.S. EPA). Registration for TPT hydroxide was cancelled in California in 1983. TPT acetate and hydroxide were banned from use in the European Union (EU) in 2002 (Lo et al., 2003). This review presents and integrates information on reproductive toxicity from the triphenyltin hydroxide (TPTH) registration database made available through the Freedom of Information Act (FOIA), and includes papers on mammalian reproductive toxicity of other TPT salts. In this review, information from the pesticide r egistration data is presented in some expatiate since it is not available.Estimates of exposure for total tin indicate that the main route in the general population is from food, about 4 mg/d. A national survey in the United States in 1982 reported 8.7-15 g tin/g in human adipose tissue (ATSDR, 1992). However, these estimates are based on outdated information, and much of the tin came from canned foods (inorganic tin) (ATSDR, 1992). The most recent information for TPT is from Japan (Tsuda et al., 1995). Duplicate region studies indicated an intake of 0.7 g TPT/d in 1991 and 1992, and market basket surveys indicated intakes of 5.4 and 1.3 g TPT/d in 1991 and 1992, respectively. analytical techniques are now becoming available to separate various forms of inorganic and organic tin which engagement more accurate human exposure assessment.Chemical equations2Na + C6H5Cl C6H5Na + NaCl4 C6H5Na +SnCl4 (C6H5)4Sn + 4NaClReagents required275 ml of dry toluene (350 ml if wet)35 ml of chloro benzene15 gm of sodium10 ml of SnCl4Dry drinking glassSpecial apparatus required500 ml, three neck, round-bottom flaskVariacHigh-speed displace tug reachring rod with sharp metal bladesCylinder of argonAbout 1000 ml of coal oil in paneExtra sintered-glass funnels and filter flaskProcedureFifteen grams of clean sodium chunks and 250 ml of dry toluene are placed in the flask. A thermometer and an argon inlet tube are inserted through one of the side arm of the flask. The other side arm is Stoppard. Insert the stirrer through the main mouth of the flask, taking care of that the rousing blades cannot hit the thermometer and that they are above the chunks of sodium. While stirring gently, and with a slow stream of argon flowing, heat the contents slowly to 105. Then lower the stirrer so that the blades are about 1cm from the bottom of the flask and turn the stirrer on replete(p) power. It will be found requirement to increase the power input to the heating mental in order to keep the temperature at 105. After about 10 min of vigorous stirring at 105, remove the heating mantle from the flask. When the temperature has fallen to 99, stop the stirrer and dispense with the flask to cool to room temperature. The sodium should now be in the form of fine sand. Stir the sodium gently to see if any of the particles have agglomerated. If so, the process must be repeated. If the sodium statistical distribution is not be used immediately, thoroughly flush the flask with the argon and tightly stopper it. use the heating mantle, heat the dispersion, with moderately vigorous stirring, to 45. Attach a dropping funnel containing 35 ml of chlorobenzene to the unused side arm and add 2 to 3 ml of the chlorobenzene to the flask.Notice The flask should never contain more than 3 ml of un reacted chlorobenzene If more than this amount is present, an uncontrollably vigorous chemical reaction may take place, resulting in a fire.Remove the heating mantle from the flask. The reaction should start, as demonstrate by a rise in the temperature. If the reaction does not start at 45, cautiously rise the temperature to 50 (no higher). If the reaction starts at this temperature, the temperature may suddenly rise to as high as 55, so be ready to cool the flask quickly with the kerosene bath. (If the reaction does not start at 50, cool the flask to room temperature, cautiously hydrolyze the form with alcohol, and discard).Temperature in access of 50 will not cause great harm at the runner of the synthesis, but thereafter the temperature must be kept below 45 keep the flask part immersed in the kerosene bath and cool the kerosene bath by occasionally adding pieces of DRY chicken feed to it. The temperature of the reaction mixture may be held between 40 and 45 by adjusting the rate of addition of chlorobenzene.After all the chlorobenzene has been added (about 1 to 2 hours), place a solution of 10ml of stannic chloride in 25ml of toluene in the dropping funnel, and, over a period of 30 min, add this solution to the reaction flask. During this addition, it is necessary to cool the flask so as to keep the temperature below 45. The flask now be stored indefinitely (without protection from the air) until the tin tetra phenyl is extracted from the mixture.Wipe the kerosene from the bottom of the flask, and, with moderate stirring, heat the mixture to inchoate boiling and quickly filter through a sintered-glass funnel. It is best to keep most of the solid symmetry in the reaction flask. Cool the filtrate to room temperature and filter off the product on other(prenominal) sintered-glass funnel. Return the filtrate to the original flask and repeat the extraction two or three time until no more product precipitates on cooling the solution to room temperature. It is helpful to add another 100 ml of toluene to the mixture to reduce the necessary number of extractions. The final solution should be cooled in an ice bath before filtering. Suck the crystal s of tin tetra phenyl as dry as potential on the filter and then let them air dry for 4 to 20 hours on a watch glass.A yield of about 25 gm of material melting at 266 to 228 should be obtained. A pure product (melting at 299) may be obtained by re crystallization from benzene or toluene.RESULTS AND DISCUSIONPhysical data for reported compounds are given in Table 1.Compound data-based formulaM.P (C)Solubility% Yield1.(C6H5)4Sn110-112Toluene, Ethanol, Chloroform72IR spectroscopyIR is one of the most important spectroscopic methods used for qualitative and quantitative analysis. It is based on the fact that each compound has its own unique spectra and certain functional groups absorbat about the same wavelength even in different molecules. Its one most important use has been for the identification of organic compounds whose spectra are generally complex and provide many maxima and minima that are used for comparison purposes. Indeed in most instances the IR spectrum of the compounds especially of organic compounds provides a unique finger print, which is readily distinguished from the absorption pattern from all other compounds because only optic isomers absorb in the same way. Absorption of IR radiation is confined largely to molecular species for which small energy differences exist between various vibration and rotational states. As for as spectrum is concerned we see a prominent prime at 457cm-1, which indicates the formation of metal to carbon bond, which shows the formation of our product. For aliphatic CH peak appear at 3057 cm-1 .ReferencesP. Powell, Principles of Organometallic Chemistry, (1988), 2nd edition, Chapman and Hall, new-fangled York, pp-1-10.T.Mole and E.A Jaffery, Organometallic Compounds, (1972), 3rd edition, Elsvier Publishing Company, London, pp.89-92.F. Albert and Geoffrey Wilkinson, Advanced Inorganic Chemistry, (1962), 3rd edition, Interscience Publishers, New York, pp-310-312.J.C Bailar, H.J Emeleus, S.R Nhylom and A.F Trotman, C omprehensive Inorganic Chemistry, (1973), 2nd edition, Prgmon, New York, pp.153-157.J.C Bailar, H.J Emeleus, S.R Nhylom and A.F Trotman, Comprehensive Inorganic Chemistry, (1973), 4th edition, Prgmon, New York, pp.89-93.J.W Robinson, Undergraduate implemental Analysis, 5th Edition,(995),Marcel Dekker, New York,pp.166-168.A.U Rehman, Nuclear Magnetic Resonance, 1st edition,(1989),pp.90-93.