Sn Al complexes

Spectral analysis of μ-bridging coordination in triphenyl Sn(IV)-Al(III)-μ-oxoisopropoxide derivatives of alkylpyruvate aroylhydrazone: Interpretation of pharmacophore geometries

Rajni Johar, Rajiv Kumar, Ashok K Prasad

Abstract


Triphenyl Sn(IV)-A(lII)-µ-oxoisopropoxide derivatives having different (NOONO and OONO) backbones were obtained by the reaction of triphenyltin acetate and aluminium isopropoxide with corresponding ligand. Through manipulation of reaction stoichiometry, varieties of coordination compounds featuring µ-bridging coordination were obtained. 119Sn NMR spectra of Ph3SnOAl(OPri)L and Ph3SnOAl(L)2 exhibit a single resonance, in solution, which is a characteristic of four-coordinated triphenyl complex. There are quite close structural and architectural similarities between both series of complexes. Physicochemical analysis confirmed the formation of Ph3SnOAl(OPri)L and Ph3SnOAl(L)2 derivatives. Both the derivatives of triphenyl Sn(IV)-Al(III)-µ-oxoisopropoxide showed tetra- and penta- coordination of metal centres with distorted tetrahedral and distorted trigonal-bipyramidal geometries for Sn(IV) and Al(III) respectively. These central metal ions are capable of organizing surrounding atoms to achieve pharmacophore geometries by the variation of architectural elements of concerned ligands which are not readily and rapidly achieved by other means. Five complexes from each series were screened for their anti-fungal and antibacterial properties.


Keywords


organotin(IV) alkylpyruvate aroylhydrazones; 27Al NMR; 119Sn NMR and MS-spectroscopy

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References


Pietrzykowski, T. Skrok, S. Pasynkiewicz, M. Brzoska-Mizgalski, J. Zachara, R. Anulewicz-Ostrowska, K. Suwinska and L.B. Jerzykiewicz, Reactions of methyl- and ethylaluminum compounds with alkoxyalcohols. The influence of alkoxyalcohol substituents on the structure of the complexes formed, Inorg. Chim. Acta. 2002, 334, 385-394.

C.-H. Lin, B.-T. Ko, F.-C. Wang, C.-C. Lin and C.-Y. Kuo, Electronic and steric factors affecting the formation of four or five-coordinated aluminium complexes: syntheses and crystal structures of some aluminum alkoxides, J. Organomet. Chem. 1999, 575, 67-75.

H. Yi-Lun, K. Bor-Hunn, Bao-Tsan, L. Chu-Chieh, Reactions of amides with organoaluminium: a useful synthetic route to aluminium diketiminates, J. Chem. Soc., Dalton Trans. 2001, 1359-1365.

D.A. Atwood and B.C. Yearwood, The future of aluminium chemistry, J. Organomet. Chem. 2000, 600, 186-197.

M. Gielen, P. Lelieveld, D. de Vos, R. Willem, Metal based antitumour drugs. Vol. 2, Freund, Tel Aviv, 29-54, 1992.

M. Gielen, E.R.T. Tiekink, Metallotherapeutic drugs and metal-based diagnostic agents: The use of metals in medicine, John Wiley & Sons, New York, 2005.

Ambrosini, E. Bertoli, G. Zolese, F. Tanfani, Interaction of tributylin acetate and tributyltin chloride with dipalmitoyl phosphatidylcholine model membrane. Chem. Phys. Lipids. 1991, 59, 189-197.

R.M. Fernandes, E.S. Lang, E.M.V. Lopez and G.F. Desousa, Organotin(IV) complexes of 4,6-dimethylpyrimidine-2-thione,Me2PymtH. Preparation, characterization and crystal structure determination of cis-[Ph2Sn(Me2Pymt)2] and [Ph3Sn(Me2Pymt)], Polyhedron, 2002, 6, 1149-1153.

S.J. Obrey, S.G. Bott, A.R. Barron, A lewis base promoted alkyl/alkoxide ligand redistribution: reaction of [Me2Al(m-OCPh3)]2 with THF, Organometallics, 2001, 20, 5119-5124.

M. Gielen. Tin-based antitumour drugs, Coord. Chem. Reviews, 1996, 151, 41-51.

O. Koper, I. Lagadic, K.J. Klabunde, Destructive adsorption of chlorinated hydrocarbons on ultrafine (Nanoscale) particles of calcium oxide. 2. Chem. Mater, 1997, 9, 838-842.

J. Devi, R. Kumar, Synthesis, spectral and thermal studies on schiff base derivatives of heterobimetallic [Ca(II)-Ti(IV)]-µ-oxoisopropoxide, Chem. Sci. Trans., 2013, 2(4), 1214-1221.

(a) A.I. Vogel, A text book of quantitative analysis, Longman: London; 1989. (b) D.D. Perrin, W.L.F. Armarego, D.R. Perrin. Purification of laboratory chemicals, 2nd ed., Pergamon Press: New York; 1980.

E. Clementi, G. Corongiu. (Eds) Methods and techniques in computational chemistry: METECC-95, STEF, Cagliari, 1995;

M. Sharma, A. Singh, R.C. Mehrotra. Synthesis and characterization of homo- and heterobimetallic diethanolaminates of alkaline earth metals. Polyhedron, 2000, 19, 77-83. [Symptoms such as wheezing, cough, chest pain and dyspnoea on exertion reported in workers handling SnCl4 were probably due to elevated levels of hydrogen chloride formed by the combination of SnCl4 and water in the presence of heat]

K. Nakamoto. Infrared and raman rpectra of inorganic and coordination compounds, John Wiley and Sons, New York, 1986.

M.B. Jones, C.E. MacBeth, Tripodal phenylamine-based ligands and their CoII complexes Matthew B. Jones and Cora E. Mac Beth, Inorg. Chem. 2007, 46, 8117-8119.

G. Sébastien, A. Sabrina, R. Patrice, P. Stéphane, D. Jean-Rogers, D. Michel, A spectroscopic investigation of the complexing ability of catecholate or salicylate derivatives towards aluminium(III), Polyhedron, 2004, 23, 2393-2404.

L.J. Bellamy. The infrared spectra of complex molecules, Chapman and Hall, London, Reprinted, 1978.

N.B. Colthup. L.H. Daly, S.E. Wiberly. Introduction to infrared and raman spectroscopy, Academic Press, New York, 1990.

S. Giroux, P. Rubini, B. Henry, S. Aury, Complexes of praseodymium(III) with -gluconic acid, Polyhedron, 2000, 19, 1567-1574.

E. Breitmaier, W. Voelter. Carbon-13 NMR spectroscopy: High-resolution methods and applications in organic chemistry and biochemistry, John Wiley & Sons; 3 edition, 1986.

D. Doddrell, I. Burfitt, W. Kitching, M. Bullpitt, L. Che-Hung, R.J. Mynott, J.L. Considine, H.G. Kuivila, R.H. Sarma. Carbon-13 Fourier transform NMR study of the organotin compounds. II. Karplus-type dependence of vicinal tin-119-carbon-13 coupling J. Am. Chem. Soc., 1974, 96, 1640-1642

Lyčka, D. Micák, j. Holeček, M. Biesemans, J.C. Martins, R. Willem. 13C-119Sn Correlation NMR in Solution and Solid-State CP/MAS NMR of Bis(tributylstannyl(IV)) O-5,6-Isopropylidene-l-(+)-ascorbate, Organometallics, 2000, 19, 703-706.

S. Shaukat, R. Zia-ur, M. Niaz, S. Afzal, A. Saqib, K. Nasir, M. Auke. Bioactive hepta- and penta-coordinated supramolecular diorganotin(IV) Schiff bases, J. of Organomet. Chem., 2013, 741, 59-66.

G. Shadab, M. Majid, T. Shahram, M. Valiollah, B. Iraj Mohammad poor, B. Behjat, S. Faranak. High-valent tin(IV) porphyrins: Efficient and selective catalysts for cyclopropanation of styrene derivatives with EDA under mild conditions, J. of Organomet. Chem. 2013, 741, 78-82.

T. Jan, K. Hana, P. Zdenka, R. Ales. Preparation and structure of tin(IV) catecholates by reactions of C,N-chelated tin(IV) compounds with a catechol or lithium catecholate, and various stannylenes with a quinone, J. of Organomet. Chem. 2013, 745, 25-33

R. Benn, A. Rufinska, H. Lehmkul, E. Janssen, C. Kruger. 27Al-NMR spectroscopy: a probe for three-, four-, five-, and six-fold coordinated Al atoms in organoaluminum Compoundsc. Angew. Chem. Int. Ed. Engl. 1983, 22, 779-780.

M. Pellei, G.G. Lobbia, M. Ricciutelli, C. Santini. Synthesis and spectroscopic characterization of new organotin(IV) complexes with bis(3,5-dimethylpyrazol-1- yl)dithioacetate. J. Coord. Chem. 2005, 58, 409-420.

A.A. Abou-Hussen, N.M. EL-Metwally, E.M. Saad, A.A.

EL-Asmy, Spectral, magnetic, thermal and electrochemical studies on phthaloyl bis(thiosemicarbazide) complexes. J.of Coord. Chem. 2005, 58, 1735-1749

H. Chin, B.R. Penfold. Crystal and molecular structures of two polymeric organotin carboxylates, C15H12O2Sn, C5H9F3O2Sn. J. Crystal Mol. Struct. 1973, 3, 285-297.

K. Wakamatsu, A. Orita, J. Otera. Evaluation of tin-oxygen bond association by means of ab initio molecular orbital calculations. Organometallics, 2008, 27, 1092-1097

F.M. Bickelhaupt, E.J. Baerends, K.B. Lipkowitz, D.B. Boyd. Reviews in Computational Chemistry, Wiley-VCH, New York, 2000, 15, 1-86.

Rahman, M.I. Choudhary. Thomsen, W.J. Bioassay techniques for drug development, Harwood Academic Press, Amsterdam 2001.

M.M. Pour, V. Špulák, J. Balšánek, V. Kuneš, B. Waisser. 3-Phenyl-5-methyl-2H,5H-furan-2-ones: tuning antifungal activity by varying substituents on the phenyl ring. Bioorg. Med. Chem. Lett., 2000, 10, 1893-1901.

R.D. Pearson, A.A. Manian, D. Hall, J.L. Harcus. Antileishmanial activity of chlorpromazine. Antimic. Ag. Chemo. 1984, 25, 571-574.

W. Rehman, K.B. Musa, B. Amin. Comparative study of structure: activity relationship of di and triorganotin (IV) complexes of monomethyl glutarate. J. Braz. Chem. Soc. 2005, 16, 827-834.

F.M. Morad, M.M. Ajaily, S.B. Gweirif. Preparation, physical characterization and antibacterial activity of Ni(II) schiff base complex. J. of Science and Its Applications, 2007, 1, 72-78.

P. Spigaglia, F. Barbanti, P. Mastrantonio. Detection of a genetic linkage between genes coding for resistance to tetracycline and erythromycin in Clostridium difficile. Microb. Drug Resist. 2007, 13, 90-95.

Xiong-Bin, Y. Qiong, W. Qian, S. Yu-Mei, X. Ren-Gen, Y. Xiao-Zeng. The first organometallic carbonyl tungsten complex of antibacterial drug norfloxacin. Inorg. Chem. Commun. 2004, 7, 1302-1305.

Y. Wang, G.R. Wang, A. Shelby, N.B. Shoemaker, A.A. Salyers. A newly discovered bacteroides conjugative transposon, CTnGERM1, Contains genes also found in gram-positive bacteria. Appl. Environ. Microbiol. 2003, 69, 4595-4603.

B.S. Chhikara, A.K. Mishra, V. Tandon. Synthesis of bgifunctional chelating agents to label monoclonal antibodies for radioimmunodiagnosis of cancer. Int. Arch. Sci. Technol., 2006, 6(1), 5-9.

R. Johar, R. Kumar, A.K. Aggarwal. Tailoring methodologies for the architecture of organometallic frameworks of Bi(V) derived from antibiotics: Spectral, MS, XRPD and molecular modeling with antifungal effectiveness. J Integr Sci Technol, 2013, 1(1), 54-64.

Pauling, L. Nature of the chemical bond”, Cornel University Press, 2nd. Ed, Cornell, New York, USA (1947) 251.

Nugent, W.A.; Mayer, J.M. Metal-ligand multiple bonds, Wiley Interscience, New York, USA (1988).






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