Synthesis and Structural Studies on Tetranuclear Tin Compositions Containing Tin {[R2Sn(LH)]2O}2 Moieties (R = Bu or Oct and LH = 4-[((E)-1-{2-Hydroxy-5-[(E)-2-(aryl)-1-diazenyl]phenyl}methylidene)- amino]benzoate)

Diorganotin compounds containing tetranuclear tin compositions of the type {[R2Sn(LH)]2O}2 in which LH is deprotonated carboxylic acid LHH′ (H′ are the carboxylic and H the phenolic protons of the benzoic acid) HO2C–C6H4-4-{N=C(H)C6H3-2-OH-5-(N=N–C6H4X)} (X = H for L1H, X = 2-CH3 for L2H, X = 3-CH3 for L3H, and X = 4-CH3 for L4H; R = Bu or Oct), were synthesized and characterized by FT-IR, NMR, and 119Sn Mossbauer spectroscopy. One of the complexes, {[Oct2Sn(O2CC6H4{N=C(H)C6H3-2-OH-5-(N=NC6H4CH3-2)})]2O}2 was characterized by single-crystal X-ray diffaraction, which revealed that the compound is a centrosymmetric tetranuclear bis(dicarboxylatotetrabutyldistannoxane) complex with a planar Sn4O2 core. The two μ3-oxo oyxgen atoms are connected to a Sn2O2 ring and to two exocyclic tin atoms. The four carboxylate ligands display two different modes of coordination. Both modes of coordination involve bridging two structurally distinct tin atoms. The solution structures of the complexes were unravelled by 119Sn NMR spectroscopy, and found to be identical to those of the crystalline state.

[1]  S. Pyke,et al.  The synthesis, characterization and structures of some 4-[((E)-1-{2-hydroxy-5-[(E)-2-(aryl)-1-diazenyl]phenyl}methylidene)amino]benzoic acid , 2009 .

[2]  Anthony L. Spek,et al.  Structure validation in chemical crystallography , 2009, Acta crystallographica. Section D, Biological crystallography.

[3]  M. Holčapek,et al.  Di-n-octyltin(IV) complexes with 5-[(E)-2-(aryl)-1-diazenyl]-2-hydroxybenzoic acid: Syntheses and assessment of solid state structures by 119Sn Mössbauer and X-ray diffraction and further insight into the solution structures using electrospray ionization MS, 119Sn NMR and variable temperature NMR sp , 2007 .

[4]  A. Linden,et al.  Synthesis, spectroscopic characterization of tribenzyltin(IV) complexes of polyaromatic carboxylic acid ligands: Crystal and molecular structures of Bz3Sn[O2CC6H4{NN(C6H3-4-OH(C(H)NC6H4X-4))}-o](OH2) (X = –Cl, –OCH3) , 2006 .

[5]  M. Holčapek,et al.  Synthesis and characterization of bis[dicarboxylatotetraorganodistannoxane] units involving 5 -[ (E) -2 -(aryl)-1 -diazenyl ] -2 -hydroxybenzoic acids : An investigation of structures by X-ray diffraction, NMR, electrospray ionisation MS and assessment of in vitro cytotoxicity , 2006 .

[6]  A. Linden,et al.  2-{(E)-3-[(E)-4-Bromo­phenyl­imino­meth­yl]-4-hydroxy­phenyl­diazen­yl}benzoic acid toluene hemisolvate , 2006 .

[7]  L. Pellerito,et al.  Biological activity studies on organotin(IV)n+ complexes and parent compounds , 2006 .

[8]  A. Orita,et al.  Fluorophilicity switch by solvation. , 2006, Journal of the American Chemical Society.

[9]  M. Holčapek,et al.  Synthesis, characterization, cytotoxic activity and crystal structures of tri- and di-organotin(IV) complexes constructed from the β-{[(E)-1-(2-hydroxyaryl)alkylidene]amino}propionate and β-{[(2Z)-(3-hydroxy-1-methyl-2-butenylidene)]amino}propionate skeletons , 2006 .

[10]  K. Ohkubo,et al.  Organotin perfluorooctanesulfonates as air-stable Lewis acid catalysts: synthesis, characterization, and catalysis. , 2006, Chemistry.

[11]  A. Linden,et al.  catena-Poly[[tri-n-butyl­tin(IV)]-μ-2-{(E)-4-hydr­oxy-3-[(E)-4-methyl­phenyl­imino­meth­yl]phenyl­diazen­yl}benzoato-κ2O:O′] , 2005 .

[12]  L. Pellerito,et al.  Embryotoxicity studies of tri‐n‐butyltin(IV) complexes of 5‐[(E)‐2‐(aryl)‐1‐diazenyl]‐2‐hydroxybenzoic acid and 2‐[(E)‐2‐(3‐formyl‐4‐hydroxyphenyl)‐1‐diazenyl] benzoic acid on sea urchin development , 2005 .

[13]  M. Holčapek,et al.  Synthesis, characterization and crystal structures of polymeric and dimeric triphenyltin(IV) complexes of 4-(((E)-1-{2-hydroxy-5-((E)-2-(2-carboxyphenyl)-1- diazenyl)phenyl}methylidene)amino)aryls , 2005 .

[14]  M. Holčapek,et al.  Electrospray ionization mass spectrometry of tributyltin(IV) complexes and their larvicidal activity on mosquito larvae: crystal and molecular structure of polymeric (Bu3Sn[O2CC6H4{NN(C6H3‐4‐OH(C(H)NC6H4OCH3‐4))}‐o])n , 2005 .

[15]  D. Balköse,et al.  Thermal stabilisation of poly(vinyl chloride) by organotin compounds , 2005 .

[16]  Ray J. Butcher,et al.  A quasi‐planar polyaromatic compound containing an azo and a Schiff base linkage , 2005 .

[17]  J. Bordado,et al.  Recent Developments in Polyurethane Catalysis: Catalytic Mechanisms Review , 2004 .

[18]  J. Otera,et al.  Toward ideal (trans)esterification by use of fluorous distannoxane catalysts. , 2004, Accounts of chemical research.

[19]  A. Orita,et al.  Assessment of fluoroalkyltin compounds as fluorous Lewis acid catalysts , 2003 .

[20]  D. Balköse,et al.  Tin soaps in emulsion PVC heat stabilization , 2002 .

[21]  A. Orita,et al.  A Practical and Green Chemical Process: Fluoroalkyldistannoxane-Catalyzed Biphasic Transesterification. , 2001, Angewandte Chemie.

[22]  A. Orita,et al.  Distannoxane-Catalyzed Highly Selective Acylation of Alcohols. , 1998, The Journal of organic chemistry.

[23]  E. Tiekink,et al.  On the assignment of 119Sn resonances of bis[dicarboxylatotetraorganodistannoxanes] in solution and solid state 119Sn NMR spectra , 1998 .

[24]  L. Pellerito,et al.  Syntheses and Solid-State Structures of Some Dialkyltin Derivatives of α-Methoxy- and α-Acetoxy-phenylacetic Acids , 1996 .

[25]  R. Houghton,et al.  The role of μ-hydroxy and μ-alkoxy binuclear complexes in tin(IV)-catalysed urethane formation , 1996 .

[26]  E. Tiekink,et al.  Crystal structure of the dimeric bis(p-fluoro- and pentafluorophenylacetato)tetra-n-butyldistannoxanes , 1995 .

[27]  H. Nozaki,et al.  Novel template effects of distannoxane catalysts in highly efficient transesterification and esterification , 1991 .

[28]  T. P. Lockhart,et al.  Structural studies of diorganotin(IV) carboxylates. X-ray and NMR structures of Me2Sn(OAc)2 and a 7-coordinate tin anion, Me2Sn(OAc)3NMe4.cntdot.2CHCl3 , 1987 .

[29]  A. Lyčka,et al.  13C and 119Sn NMR spectra of di-n-butyltin(IV) compounds , 1986 .

[30]  T. Yano,et al.  Tin-119 NMR spectroscopic study on tetraorganodistannoxanes , 1985 .

[31]  J. Zubieta,et al.  STRUCTURAL TIN CHEMISTRY , 1979 .

[32]  A. G. Davies,et al.  Organotin chemistry : IX. Investigations of the structure of some 1,3-difunctional tetraalkyl distannoxanes by mössbauer spectroscopy and 119Sn Heteronuclear double magnetic resonance , 1971 .

[33]  R. Herber,et al.  Systematics of Mössbauer Isomer Shifts of Organo‐Tin Compounds , 1965 .

[34]  N. Hadjiliadis,et al.  Antiproliferative and anti-tumor activity of organotin compounds , 2009 .

[35]  G. Sheldrick.  A short history of SHELX. , 2008, Acta crystallographica. Section A, Foundations of crystallography.

[36]  J. Wardell,et al.  Crystal structures of [(IMe2SnOSnMe2OEt)2] and [{(PrCO2)Me2SnOSnMe2(O2CPr)2}2] , 1997 .

[37]  Edward R. T. Tiekink,et al.  Structural chemistry of organotin carboxylates: a review of the crystallographic literature , 1991 .

[38]  T. Kanzawa,et al.  Tetraalkyldistannoxanes as catalysts for urethane formation , 1967 .