Preparation and structural characterization of simple and donor-substituted triorganostannyl 1′-(diphenylphosphino)-1-ferrocenecarboxylates and their P-chalcogenide derivatives

Journal of Organometallic Chemistry

Volumn 695, Issue 2, 2010, Pages 271-279

  Štěpnička, Petr ^a   Císařová, Ivana ^a   Růžička, Aleš ^b  

^a CHARLES UNIVERSITY   (Czech Republic)

^b UNIVERSITY OF PARDUBICE   (Czech Republic)

Author keywords

Cyclic voltammetry; Ferrocene; Organotin esters; Phosphine chalcogenides; Phosphinocarboxylic ligands; Structure elucidation

Indexed keywords

CHALCOGENS; COORDINATION ENVIRONMENT; DOUBLE BONDS; ELEMENTAL SULFUR; FERROCENES; HYDROGEN BOND DONORS; LINEAR ASSEMBLY; MASS SPECTROSCOPY; MULTINUCLEAR NMR; ORGANOTIN ESTERS; PHOSPHINE CHALCOGENIDES; POLAR GROUPS; SINGLE CRYSTAL X-RAY DIFFRACTION; SOLID-STATE STRUCTURES; STRUCTURAL CHARACTERIZATION; STRUCTURE ELUCIDATION; TIN ATOMS; TRIORGANOTINS; WATER MOLECULE;

AROMATIC HYDROCARBONS; CARBOXYLATION; CHALCOGENIDES; CHLORINE COMPOUNDS; CYCLIC VOLTAMMETRY; ESTERIFICATION; ESTERS; FLUORINE CONTAINING POLYMERS; HYDRATES; HYDROGEN; HYDROGEN BONDS; HYDROGEN PEROXIDE; IRON COMPOUNDS; LIGANDS; MASS SPECTROMETRY; MOLECULES; ORGANOMETALLICS; OXYGEN; PHASE CHANGE MEMORY; PHOSPHORUS COMPOUNDS; POTASSIUM; SULFUR; TIN;

CRYSTAL ATOMIC STRUCTURE;

EID: 72749113336     PISSN: 0022328X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jorganchem.2009.09.042     Document Type: Article

References (43)

1. A.W. Davies, Organotin Chemistry, Wiley, Weinheim, 2004 (Chapters 13 and 23).
2. M. Gielen, E.R.T. Tiekink, in: M. Gielen, E.R.T. Tiekink (Eds.), Metallotherapeutic Drugs and Metal-Based Diagnostic Agents, Wiley, New York, 2005 (Chapter 22).
3. Hadjikakou S.K., and Hadjiliadis N. Coord. Chem. Rev. 253 (2009) 235
4. Tiekink E.R.T. Appl. Organomet. Chem. 5 (1991) 1
5. Chandrasekhar V., Nagendran S., and Baskar V. Coord. Chem. Rev. 235 (2002) 1
6. R.C. Mehrotra, R. Bohra, Metal Carboxylates, Academic Press, London, 1983 (Chapter 4.1).
7. Ng S.-W., and Zuckerman J.J. Organometallics 1 (1982) 714
8. Ng S.-W., and Zuckerman J.J. J. Organomet. Chem. 234 (1982) 257
9. Cross R.J., Farrugia L.J., Newman P.D., Peacock R.D., and Stirling D. J. Chem. Soc., Dalton Trans. (1996) 1087
10. For recent examples of organotin(IV) phosphinocarboxylates, see:. Bowen R.J., Caddy J., Fernandes M.A., Layh M., Mamo M.A., and Meijboon R. J. Organomet. Chem. 691 (2006) 717
11. Phadnis P.P., Dey S., Jain V.J., Nethaji M., and Butcher R.J. Polyhedron 25 (2006) 87
12. Zoufalá P., Gyepes R., and Štěpnička P. J. Organomet. Chem. 689 (2004) 3556
13. Zoufalá P., Císařová I., Růžička A., and Štěpnička P. Appl. Organomet. Chem. 19 (2005) 118
14. Podlaha J., Štěpnička P., Císařová I., and Ludvík J. Organometallics 15 (1996) 543
15. Štěpnička P. Eur. J. Inorg. Chem. (2005) 3787
16. Štěpnička P. In: Štěpnička P. (Ed). Ferrocenes: Ligands. Materials and Biomolecules (2008), Wiley, Chichester (Chapter 5)
17. 2O and the respective acid, see: M.S. Kumar, S. Upreti, H.P. Gupta, A.J. Elias, J. Organomet. Chem. 691 (2006) 4708.
18. Smith P.J., and Tupčiauskas A.P. Ann. Rep. NMR Spectrosc. 8 (1978) 291
19. Wrackmeyer B. Ann. Rep. NMR Spectrosc. 16 (1985) 73
20. J. Chalupa, K. Handlíř, I. Císařová, R. Jirásko, J. Brus, A. Lyčka, A. Růžička, J. Holeček, J. Organomet. Chem. 691 (2006) 2631, and references cited therein.
21. Chalupa J., Handlíř K., Padělková Z., Vejcová M., Buchta V., Jirásko R., and Růžička A. Appl. Organomet. Chem. 22 (2008) 308
22. Štěpnička P., Schulz J., Císařová I., and Fejfarová K. Collect. Czech. Chem. Commun. 72 (2007) 453
23. 13C-NMR-Spektroskopie, Thieme, Stuttgart, 1984 (Chapter 4).
24. Smith D.R., and Tieking E.R.T. Z. Kristallogr. 213 (1998) 605 (Sn-O 2.203(4), Sn-O 2.381(4) Å at 200 K)
25. Chih H., and Penfold B.R. J. Cryst. Mol. Struct. 3 (1973) 285 (Sn-O 2.205(3), Sn-O 2.391(4) Å at room temperature)
26. Smith P.J., Day R.O., Chandrasekhar V., Holmes J.M., and Holmes R.R. Inorg. Chem. 25 (1986) 2495 (at 23 °C)
27. A.W. Addison, T.N. Rao, J. Reedijk, J. van Rijn, G.C. Verschoor, J. Chem. Soc., Dalton Trans. (1984) 1349 (the parameter takes 1.00 for ideal trigonal bipyramid and 0.00 for ideal square pyramid).
28. 3 (Fc = ferrocenyl, X = Cl and Br; refcodes TAFNYI and ADUSIC in the Cambridge Structural Database). However, these reference structures display distinctly shorter Sn-O and Sn⋯O distances (ca. 2.07 and 2.68 Å, respectively).
29. The 'liberated' C{double bond, long}O oxygen in 1a takes part in a soft intramolecular hydrogen bonding (C20-H20⋯O1′: C20⋯O1′ = 3.365(5) Å, angle at H20 = 157°; symmetry operation: 1 - x, 1/2 + y, 1/2 - z).
30. Ng S.W., and Das V.G.K. Acta Crystallogr., Sect. C: Cryst. Struct. Commun. 52 (1996) 1373
31. Diop C.A.K., Touré A., Diop L., and Welter R. Acta Crystallogr., Sect. E: Struct. Rep. Online 62 (2006) m3338
32. Ma C., Sun J., and Zhang R. J. Organomet. Chem. 691 (2006) 5873
33. Mach K., Kubišta J., Císařová I., and Štěpnička P. Acta Crystallogr., Sect. C: Cryst. Struct. Commun. 58 (2002) m116
34. An intermolecular C19-H19⋯O1 contact with C19⋯O1 being 3.288(4) Å between molecules related by elemental translation along x-axis was detected.
35. Crystallisation from dry solvents was unsuccessful starting only when some adventitious water was present.
36. A supportive C14-H14⋯O1 contact between molecules relating by translation along the a-axis (C14⋯O1 = 3.473(4) Å) was detected.
37. An additional C23-H23⋯O1 contact between molecules relating by translation along the a-axis (C23⋯O1 = 3.242(5) Å) was detected.
38. Růžička A., Jambor R., Brus J., Císařová I., and Holeček J. Inorg. Chim. Acta 323 (2001) 163
39. Kushlefsky B., Simmons I., and Ross A. Inorg. Chem. 2 (1963) 187
40. Z. Otwinowski, W. Minor, H.K.L. Denzo, Scalepack Program Package, Nonius BV, Delft, The Netherlands [For a reference, see: Z. Otwinowski, W. Minor, Meth. Enzymol. 276 (1997) 307].
41. Altomare A., Burla M.C., Camalli M., Cascarano G.L., Giacovazzo C., Guagliardi A., Moliterni A.G.G., Polidori G., and Spagna R. J. Appl. Crystallogr. 32 (1999) 115
42. G.M. Sheldrick, shelxl97. Program for Crystal Structure Refinement from Diffraction Data, University of Göttingen, Göttingen, 1997.
43. Spek A.L. J. Appl. Crystallogr. 36 (2003) 7