The 1H, 13C, 15N and 117Sn NMR study of the intramolecular Sn-N interaction in tri- and tetraorganotin compounds containing the chiral 2-(4-isopropyl-2-oxazolinyl)-5-phenyl ligand

Journal of Molecular Structure

Volumn 733, Issue 1-3, 2005, Pages 29-39

  Cmoch, Piotr ^a,b   Urbańczyk Lipkowska, Zofia ^a   Petrosyan, Armine ^c   Stȩpień, Anita ^a   Staliński, Krzysztof ^a  

^a INSTITUTE OF ORGANIC CHEMISTRY   (Poland)

^b INDUSTRIAL CHEMISTRY RESEARCH INSTITUTE   (Poland)

^c A N NESMEYANOV INSTITUTE OF ORGANOELEMENT COMPOUNDS   (Russian Federation)

Author keywords

Intramolecular coordination; Multinuclear NMR spectroscopy; N ligands; Organotin halides and hydrides

Indexed keywords

COUPLING CONSTANTS; STANNANES; TIN HYDRIDES;

CHARACTERIZATION; HYDRIDES; NITROGEN; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; ORGANOMETALLICS;

TIN COMPOUNDS;

2 [(2 BROMODIBUTYLSTANNANYL)PHENYL] 4 ISOPROPYL 4,5 DIHYDROOXAZOLE; 2 [(2 BROMODIMETHYLSTANNANYL)PHENYL] 4 ISOPROPYL 4,5 DIHYDROOXAZOLE; 2 [(2 CHLORODIBUTYLSTANNANYL)PHENYL] 4 ISOPROPYL 4,5 DIHYDROOXAZOLE; 2 [(2 CHLORODIMETHYLSTANNANYL)PHENYL] 4 ISOPROPYL 4,5 DIHYDROOXAZOLE; 2 [(2 IODODIBUTYLSTANNANYL)PHENYL] 4 ISOPROPYL 4,5 DIHYDROOXAZOLE; 2 [(2 IODODIMETHYLSTANNANYL)PHENYL] 4 ISOPROPYL 4,5 DIHYDROOXAZOLE; 4 ISOPROPYL 2 (2 TRIBUTYLSTANNANYLPHENYL) 4,5 DIHYDROOXAZOLE; 4 ISOPROPYL 2 (2 TRIMETHYLSTANNANYLPHENYL) 4,5 DIHYDROOXAZOLE; [2 (4 ISOPROPYL 2 OXAZOLINE) 5 PHENYL]DIBUTYLTIN; [2 (4 ISOPROPYL 2 OXAZOLINE) 5 PHENYL]DIMETHYLTIN; BENZENE DERIVATIVE; DIBUTYL BIS[2 (4 ISOPROPYL 4,5 DIHYDROOXAZOLINE)PHENYL]STANNANE; DIMETHYL BIS[2 (4 ISOPROPYL 4,5 DIHYDROOXAZOLINE)PHENYL]STANNANE; LIGAND; NITROGEN; ORGANOTIN COMPOUND; TIN; UNCLASSIFIED DRUG;

ANALYTIC METHOD; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL ANALYSIS; CHEMICAL BOND; CHEMICAL INTERACTION; CHEMICAL REACTION KINETICS; CHIRALITY; COMPLEX FORMATION; DRUG STRUCTURE; NITROGEN NUCLEAR MAGNETIC RESONANCE; PROTON NUCLEAR MAGNETIC RESONANCE; STRUCTURE ANALYSIS;

EID: 8144229284     PISSN: 00222860     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.molstruc.2004.07.035     Document Type: Article

References (41)

1. J.T.B.T. Jastrzebski, and G. van Koten Adv. Organomet. Chem. 35 1993 241
2. S.J. Blunden, P.A. Cusack, and R. Hill The Industrial Uses of Tin Chemicals 1985 Royal Society of Chemistry London
3. M. Gielen, R. Willem, J. Holeček, and A. Lyčka Main Group Met. Chem. 16 1993 29 and references therein
4. B. Wrackmeyer Annu. Reports NMR Spectrosc. 38 1999 203
5. B. Wrackmeyer, M. Vosteen, and W. Storch J. Mol. Struct. 602-603 2002 177
6. A. Růžička, R. Jambor, J. Brus, I. Císařová, and J. Holeček Inorg. Chim. Acta 323 2001 163 and references cited therein
7. J.T.B.H. Jastrzebski, E. Wehman, J. Boersma, G. van Koten, K. Goubitz, and D. Heijdenrijk J. Organomet. Chem. 409 1991 157
8. D. Dakternieks, K. Dunn, C.H. Schiesser, and E.R.T. Tiekink J. Chem. Soc. Dalton Trans. 2000 3693
9. G.M. Sheldrick Acta Crystallogr. A46 1990 467
10. G.M. Sheldrick shelxl97, Program for Crystal Structure Refinement 1997 University of Göttingen Germany
11. M. Peer, J.C. de Jong, M. Kiefer, T. Langer, H. Rieck, H. Schell, P. Sennhenn, J. Sprinz, H. Steinhagen, B. Wiese, and G. Helmchen Tetrahedron 52 1996 7547
12. G. Koch, G.C. Lloyd-Jones, O. Loiseleur, A. Pfaltz, R. Prétôt, S. Schaffner, P. Schnider, and P. von Matt Recl. Trav. Chim. Pays-Bas 114 1995 206
13. M.J. Brown, K.V. Baker, N. Hughs, A.J. Skarnulis, and A. Sexton J. Org. Chem. 56 1991 698
14. S.D. Rosenberg, E. Debreczeni, and E.L. Weinberg J. Am. Chem. Soc. 81 1959 972
15. B. Jousseaume, and P.J. Villeneuve J. Chem. Soc., Chem. Commun. 1987 513
16. Another way involves preparation of the copper derivatives, see: Ref. [7] and E. Wehman, G. van Koten, J.T.B.H. Jastrzebski, M.A. Rotteveel, and C.H. Stam Organometallics 7 1988 1477
17. A.E. Finholt, A.C. Bond Jr., K.E. Wilzbach, and H.I. Schlesinger J. Am. Chem. Soc. 69 1947 2692
18. W.P. Neumann, and H. Niermann Liebigs Ann. Chem. 653 1962 164
19. D.L.J. Clive, and J. Wang J. Org. Chem. 67 2002 1192
20. D.P. Curran, and G. Gualtieri SynLetters 2001 1038
21. T.N. Mitchell, and B.S. Bronk Organometallics 19 1991 936
22. The hydrides reported by Dakternieks appeared to be less stable, see Ref. [8].
23. D. Cunningham, T. Higgins, and P. McArdle J. Chem. Soc., Chem. Commun. 1984 833
24. The replacement of alkyl by phenyl groups has an influence on the tin chemical shift values. An increasing low-frequency chemical shift is observed, see: B. Wrackmeyer Annu. Reports NMR Spectrosc. 16 1995 73
25. U. Kolb, M. Dräger, and B. Jousseaume Organometallics 10 1991 2737
26. It could be explained in terms of unresolved Sn-X scalar interactions, see: Ref. [4].
27. 117Sn NMR.
28. P. Cmoch, H. Korczak, L. Stefaniak, and G.A. Webb J. Phys. Org. Chem. 12 1999 470
29. P. Cmoch, J.W. Wiench, L. Stefaniak, and J. Sitkowski J. Mol. Struct. 477 1999 119
30. F. Fu, H. Li, D. Zhu, Q. Fang, H. Pan, E.R.T. Tiekink, F. Kayser, M. Biesemans, I. Verbruggen, R. Willem, and M. Gielen J. Organomet. Chem. 490 1995 163 and references cited therein
31. R. Willem, A. Delmotte, I. De Borger, M. Biesemans, M. Gielen, F. Kayser, and E.R.T. Tiekink J. Organomet. Chem. 480 1994 255
32. F. Kayser, M. Biesemans, A. Delmotte, I. Verbruggen, I. De Borger, M. Gielen, and R. Willem Organometallics 13 1994 4026
33. F. Kayser, M. Biesemans, H. Pan, M. Gielen, and R. Willem J. Chem. Soc., Perkin Trans. 2 1994 297
34. F. Kayser, M. Biesemans, A. Delmotte, R. Hendrix, P. Malschaert, I. Verbruggen, B. Mahieu, R. Willem, and M. Gielen Bull. Soc. Chim. Belg. 103 1994 273
35. J. Yoshida, and M. Izawa J. Am. Chem. Soc. 119 1997 9361
36. E. Vedejs, A.R. Haight, and W.O. Moss J. Am. Chem. Soc. 114 1992 6556
37. J.T.B.H. Jastrzebski, D.M. Grove, J. Boersma, G. van Koten, and J.-M. Ernsting Magn. Reson. Chem. 29 1991 25
38. H. Schumann, B.C. Wassermann, and F.E. Hahn Organometallics 11 1992 2803
39. D. Dakternieks, K. Dunn, C.H. Schiesser, and E.R.T. Tiekink J. Organomet. Chem. 605 2000 209
40. K. Schwarzkopf, J.O. Metzger, W. Saak, and S. Pohl Chem. Ber./Recueil 130 1997 1539
41. A similar effect has been described, see: M. Biesemans, R. Willem, S. Damoun, P. Geerlings, M. Lahcini, P. Jaumier, and B. Jousseaume Organometallics 15 1996 2237