Complexation of triorganotin derivatives of [18] crown-6- and [15]crown-5-(benzo-4-carboxylate) with alkali thiocyanates

Chemistry - A European Journal

Volumn 7, Issue 21, 2001, Pages 4686-4695

  Kemmer, Martine ^a,b   Biesemans, Monique ^a   Gielen, Marcel ^a,b   Martins, José C ^a   Gramlich, Volker ^c   Willem, Rudolph ^a  

^a VRIJE UNIVERSITEIT BRUSSEL   (Belgium)

^b UNIVERSITÉ LIBRE DE BRUXELLES   (Belgium)

^c ETH ZURICH   (Switzerland)

Author keywords

Crown compounds; Host guest systems; NMR spectroscopy; Organotin chemistry; Structure elucidation

Indexed keywords

ACETONE; COMPLEXATION; DECOMPOSITION; DERIVATIVES; NUCLEAR MAGNETIC RESONANCE; X RAY DIFFRACTION ANALYSIS;

INTERMOLECULAR CHARGE SEPARATION;

TIN;

ALKALI; AMPHOLYTE; BENZO 15 CROWN 5 DERIVATIVE; BUTYLTIN; CARBOXYLIC ACID DERIVATIVE; CROWN 5 (BENZO 4 CARBOXYLATE); CROWN 6 (BENZO 4 CARBOXYLATE); ORGANOTIN COMPOUND; THIOCYANIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL BINDING; CHEMICAL STRUCTURE; COMPLEX FORMATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; ORGANIC CHEMISTRY; REACTION ANALYSIS;

EID: 0035813842     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/1521-3765(20011105)7:21<4686::AID-CHEM4686>3.0.CO;2-7     Document Type: Article

References (69)

1. a) I. Haiduc, F. T. Edelmann, Supramolecular Organometallic Chemistry, Wiley-VCH, Weinheim, 1999, pp. 42-43;
2. b) N. Pelizzi, A. Casnati, A. Friggeri, R. Ungaro, J. Chem. Soc. Perkin Trans. 2, 1998, 1307-1311;
3. c) P. D. Beer, J. B. Cooper, Chem. Commun. 1998, 129-130;
4. d) P. D. Beer, S. W. Dent, Chem. Commun. 1998, 825-826;
5. e) M. T. Blanda, M. A. Herren, Chem. Commun. 2000, 343-344;
6. f) J. E. Redman, P. J. Beer, S. W. Dent, M. G. B. Drew, Chem. Commun. 1998, 231-232;
7. g) M. T. Reetz, C. M. Niemeyer, K. Harms, Angew. Chem. 1991, 103, 1515-1517;
8. Angew. Chem. Int. Ed. Engl. 1991, 30, 1472-1474;
9. h) M. T. Reetz, C. M. Niemeyer, K. Harms, Angew. Chem. 1991, 103, 1517-1519;
10. Angew. Chem. Int. Ed. Engl. 1991, 30, 1474-1476;
11. i) J. Scheerder, J. P. M. van Duynhoven, J. F. J. Engbersen, D. N. Reinhoudt, Angew. Chem. 1996, 108, 1172-1175;
12. Angew. Chem. Int. Ed. Engl. 1996, 55, 1090-1093;
13. j) D. M. Rudkevich, Z. Brzozka, M. Palys, H. C. Visser, W. Verboom, D. N. Reinhoudt, Angew. Chem. 1994, 106, 480-481;
14. Angew. Chem. Int. Ed. Engl. 1994, 33, 467-468;
15. k) J.-M. Lehn, La chimie supramoléculaire, DeBoeck Université, Paris, 1997, p. 37.
16. a) D. J. Cram, Science 1988, 240, 760-767;
17. b) J. J. Christensen, D. J. Eatough, R. M. Izatt, Chem. Rev. 1974, 74, 351-384;
18. c) R. M. Izatt, K. Pawlak, J. S. Bradshaw, R. L. Bruening, Chem. Rev. 1991, 91, 1721-2085.
19. a) Crown Ethers and Analogs (Ed.: S. Pataï), Wiley, Chichester, 1989;
20. b) F. Vögtle, Supramolecular Chemistry, Wiley, Chichester, 1991;
21. c) Comprehensive Supramolecular Chemistry, Vols. I-XI (Eds.: J.-M. Lehn, J. L. Atwood, J. E. D. Davies, D. D. MacNicol, F. Vögtle), Pergamon, Oxford, 1996.
22. a) M. F. Hawthorne, X. Yang, Z. Zheng, Pure Appl. Chem. 1994, 66, 245-254;
23. b) B. Dietrich, Pure Appl. Chem. 1993, 65, 1457-1464;
24. c) F. D. Schmidtchen, M. Berger, Chem. Rev. 1997, 97, 1609-1646.
25. a) T. J. Karol, J. P. Hutchinson, J. R. Hyde, H. G. Kuivila, J. A. Zubieta, Organometallics 1983, 2, 106-114;
26. b) M. Gielen, K. Jurkschat, J. Organomet. Chem. 1984, 273, 303-312;
27. c) M. Austin, K. Gebreyes, H. G. Kuivila, K. Swami, J. A. Zubieta, Organometallics 1987, 6, 834-842;
28. d) K. Jurkschat, H. G. Kuivila, S. Liu, J. A. Zubieta, Organometallics 1989, 8, 2755-2759;
29. e) J. H. Horner, P. J. Squatritto, N. McGuire, J. P. Riebenspies, M. Newcomb, Organometallics 1991, 10, 1741-1750;
30. f) D. Dakternieks, K. Jurkschat, H. Zhu, E. R. T. Tiekink, Organometallics 1995, 14, 2512-2521;
31. g) R. Altmann, K. Jurkschat, M. Schürmann, D. Dakternieks, A. Duthie, Organometallics 1997, 16, 5716-5723;
32. h) R. Altmann, O. Gausset, D. Horn, K. Jurkschat, M. Schürmann, M. Fontani, P. Zanello, Organometallics 2000, 19, 430-443.
33. a) C. H. Yoder, R. A. Morreall, C. I. Butoi, W. J. Kowalski, J. N. Spencer, J. Organomet. Chem. 1993, 448, 59-61;
34. b)S. W. Ng, J. M. Hook, M. Gielen, Main Group Met. Chem. 1999, 22, 649-654;
35. c) S. W. Ng, Z. Kristallogr. 1999, 214, 424-426;
36. d) J. K. Tsagatakis, N. A. Chaniotakis, K. Jurkschat, S. Damoun, P. Geerlings, A. Bouhdid, M. Gielen, I. Verbruggen, M. Biesemans, J. C. Martins, R. Willem, Helv. Chim. Acta 1999, 82, 531-542;
37. e) R. Willem, M. Biesemans, F. Kayser, M. Bouâlam, M. Gielen, Inorg. Chim. Acta 1992, 197, 25-30;
38. f) S. W. Ng, V. G. Kumar Das, M. Gielen, Appl. Organomet. Chem. 1992, 6, 489-492;
39. g) R. Willem, M. Biesemans, M. Bouâlam, A. Delmotte, A. El Khloufi, M. Gielen, Appl. Organomet. Chem. 1993, 7, 311-317;
40. h) S. W. Ng, V. G. Kumar Das, J. Holeček, A. Lycka, M. Gielen, M. G. B. Drew, Appl. Organomet. Chem. 1997, 11, 39-45.
41. a) M. Gielen, Coord. Chem. Rev. 1996, 151, 41-51;
42. b) M. Gielen, P. Lelieveld, D. de Vos, R. Willem in Metal Complexes in Cancer Chemotherapy (Ed.: B. K. Keppler), VCH, Weinheim, 1993, pp. 383-390;
43. c) D. de Vos, R. Willem, M. Gielen, K. E. van Wingerden, K. Nooter, Met.-Based Drugs 1998, 5, 179-188.
44. a) E. R. T. Tiekink, Appl. Organomet. Chem. 1991, 5, 1-23;
45. b) E. R. T. Tiekink, Trends Organomet. Chem. 1994, 1, 71-116.
46. a) M. Kemmer, L. Ghys, M. Gielen, M. Biesemans, E. R. T. Tiekink, R. Willem, J. Organomet. Chem. 1999, 582, 195-203;
47. b) M. Kemmer, M. Gielen, M. Biesemans, D. de Vos, R. Willem, Met.-Based Drugs 1998, 4, 189-196;
48. c) M. Kemmer, M. Gielen, R. Willem, E. R. T. Tiekink, Main Group Met. Chem. 2000, 23, 271-275.
49. I. D. Kostas, G.-J. M. Gruter, O. S. Akkerman, F. Bickelhaupt, H. Kooijman, W. J. J. Smeets, A. L. Spek, Organometallics 1996, 15, 4450-4458.
50. a) A. Turco, C. Pecile, Nature 1961, 191, 66-67;
51. b) E. A. V. Ebsworth in Infra-Red Spectroscopy and Molecular Structure (Ed.: M. Davies), Elsevier, Amsterdam, 1963, p. 321.
52. a) L. E. Khoo, X. Chen, T. C. W. Mak, Acta Crystallogr. Sect. C 1991, 47, 2647-2649;
53. b) A. M. Domingos, G. M. Sheldrick, J. Organomet. Chem. 1974, 67, 257-263;
54. c) R. A. Forder, G. M. Sheldrick, J. Organomet. Chem. 1970, 21, 115-122.
55. K. C. Molloy in Chemistry of Tin, 2nd ed. (Ed.: P. J. Smith), Blackie Academic & Professional, Chapman Hall, London, 1998, p. 157.
56. K. Nakamoto, Infrared and Raman Spectra of Inorganic and Coordination Compounds, 4th ed., Wiley, New York, 1986, pp. 283-287 and pp. 382-383.
57. E. J. Gabe, F. L. Lee, L. E. Khoo, F. E. Smith, Inorg. Chim. Acta 1986, 112, 41-46.
58. P. G. Harrison, T. J. King, J. A. Richards, J. Chem. Soc. Dalton Trans. 1974, 1723-1726.
59. E. V. Van den Berghe, G. P. Van der Kelen, J. Organomet. Chem. 1974, 82, 345-352.
60. J. March, Advanced Organic Chemistry, 4th ed., Wiley-Interscience, New York, 1992, pp. 260-263 and references therein.
61. J. Pedersen, J. Am. Chem. Soc. 1967, 89, 7017-7036.
62. R. A. Cummins, P. Dunn, Aust. J. Chem. 1964, 17, 411-418.
63. E. Schmidt, A. I. Popov, J. Am. Chem. Soc. 1983, 105, 1873-1878.
64. a) J. Mason, Multinuclear NMR, Plenum, New York, 1987, pp. 625-629;
65. b) R. Willem, A. Bouhdid, F. Kayser, A. Delmotte, M. Gielen, J. C. Martins, M. Biesemans, B. Mahieu, E. R. T. Tiekink, Organometallics 1996, 15, 1920-1929.
66. SHELXTL software package for crystal structure determination, BROKER AXS, Madison (USA), 1997.
67. M. Bouâlam, R. Willem, M. Biesemans, B. Mahieu, J. Meunier-Piret, M. Gielen, Main Group Met. Chem. 1991, 14, 41-56.
68. a) R. B. Cody, J. Tamura, B. Musselman, Anal. Chem. 1992, 64, 1561-1570;
69. b) G. Lawson, R. H. Dahm, N. Ostah, E. D. Woodland, Appl. Organomet. Chem. 1996, 10, 125-133.