Experimental and theoretical investigations of the formation of the diazene PhSN=C (H)N=NC (H)=NSPh from HCN2(SPh)3 by a thiyl-radical-catalyzed mechanism: Identification of the HC(NSPh)2 · radical and X-ray structures of HCN2(SPh)3 and PhSN=C (H)N=NC (H)=NSPh

Inorganic Chemistry

Volumn 35, Issue 13, 1996, Pages 3839-3847

  Chivers, Tristram ^a   McGarvey, Bruce ^b   Parvez, Masood ^a   Vargas Baca, Ignacio ^a   Ziegler, Tom ^a  

^a UNIVERSITY OF CALGARY   (Canada)

^b UNIVERSITY OF WINDSOR   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000072136     PISSN: 00201669     EISSN: None     Source Type: Journal    
DOI: 10.1021/ic960317t     Document Type: Article

References (63)

1. Preston, K. F.; Sutcliffe, L. H Magn. Reson. Chem. 1990, 28, 189.
2. (a) Barton, D. H. R.; Blair, I. A.; Magnus, P. D.; Norns, R. K. J. Chem. Soc., Perkin Trans. I 1973, 1031-1037.
3. (b) Almog, J.; Barton, D. H. R., Magnus, P. D.: Norris, R. K. J. Chem. Soc., Perkin Trans. 1 1974, 853
4. Banister, A. J.; Rawson, J. M. In The Chemistry of Inorganic King Systems; Steudel, R., Ed.; Elsevier: Amsterdam, 1992; Chapter 17, p 323.
5. Cordes, A. W.; Haddon, R. C.: Oakley, R. T. In The Chemistry of Inorganic Ring Systems; Steudel, R., Ed.; Elsevier: Amsterdam, 1992; Chapter 17, p 295.
6. See. for example. Del Bel Belluz, P.; Cordes, A. W.; Kristof, E. M., Kristof, P ; Liblong, S. W.; Oakley, R. T. J. Am. Chem. Soc. 1989, 111, 9276.
7. (a) Boeré, R. T ; Moock, K. H.; Derrick, S.; Hoogerdijk. W.; Preuss, K., Yie, J. Can. J. Chem. 1993, 77, 473.
8. (b) Amin. M.; Rees, C. W. J. Chem. Soc. Chem Commun. 1989, 1137.
9. Fenske, D.; Ergezinger, C.; Dehnicke, K. Z. Naturforsch. 1989, 44B, 857.
10. Chandrasekhar, V.; Chivers, T ; Kumaravel, S S., Parvez, M.; Rao, M. N. S. Inorg. Chem. 1991, 30, 4125.
11. Chandrasekhar, V., Chivers, T.; Fait, J. F ; Kumaravel, S. S. J Am. Chem. Soc 1990, 112, 5373.
12. (a) Krause, I. M.Sc. Thesis, The University of Calgary, 1996.
13. (b) Zoricak, P.; Vargas-Baca, I.; Parvez, M.; Chivers, T Phosphorus, Sulfur Silicon Relat Elem. 1994, 93/94, 455.
14. (a) Drozdova, Y.; Steudel, R. Chem. Eur. J. 1995. 1, 193.
15. (b) Steudel, R. Angew. Chem., Int. Ed. Engl. 1995, 34, 1313.
16. (a) Chivers, T.; McGregor, K.; Parvez, M.; Vargas-Baca. I.; Ziegler, T. Can. J. Chem. 1995, 73, 1380.
17. (b) Chivers, T.; Jacobsen. H.; Vollmerhaus, R.; Ziegler, T. Can. J. Chem. 1994, 72, 1582.
18. Cordes, A. W.; Bryan, C. D.; Davis. W. M.; de Laat. R. H.; Glarum. S. H.; Goddard, J. D.; Haddon, R. C.; Hicks, R. G.; Kennepohl, D. K.; Oakley,R. T.; Scott, S. R.; Westwood, N. P. C. J. Am. Chem. Soc. 1993, 115, 7232.
19. Mueller, W, H. J. Am. Chem. Soc: 1968, 90, 2075.
20. SAPI91: Fan Hai-Fu, Structure Analysis Programs with Intelligent Control, Rigaku Corp., Tokyo, Japan, 1991.
21. DIRDIF94: Beurskens, T.: Admiraal, G.; Beurskens, G., de Gelder, R.; Israel, R ; Smits, J. M. M. Technical Report of the Crystallography Laboratory, University of Nijmegen. Nijmegen. The Netherlands. 1994.
22. Cromer, D. T ; Waber, J. T. International Tables for X-ray Crystallography; Kynoch Press: Birmingham, England, 1974; Vol. IV, Table 2-2A.
23. Ibers, J. A.; Hamilton. W. C. Acta Crystallogr. 1964. 17. 781.
24. teXsan: Crystal Structure Analysis Package, Molecular Structure Corp., 1985 and 1992.
25. SIR92: Altomare, A.; Burla, M. C.; Camalla. M.: Cascarano. M.; Giacovazzo, C ; Guagliardi. A ; Polidori, G. J. Appl. Crystallogr.. manuscript m preparation.
26. (a) Gunnarsson, O.: Lundquist. I. Phys. Rev. 1974, BIO, 1319.
27. (b) Gunnarsson, O.; Lundquist. I Phys. Rev. 1976. B13, 4274.
28. (c) Gunnarsson. O.; Johnson. M., Lundquist, I. Phys. Rev. 1979, B20. 3136.
29. Baerends, E. J.; Ellis, D. E.; Ros, P. Chem. Phys. 1973, 2, 41.
30. Baerends, E. J. Ph.D. Thesis, Frije Universiteit, Amsterdam. 1975.
31. Ravenek, W. In Algorithms and Applications on Vector and Parallel Computers; Riele, H J. J., Dekker. Th. J., van de Horst, H A., Eds.; Elsevier Amsterdam, 1987.
32. Becke, A. D. J. Chem. Phys. 1988, 88, 2547.
33. Versluis, L.; Ziegler, T. J. Chem. Phys. 1988: 88, 322.
34. Ziegler, T.; Rauk, A. Theor. Chim. Acta 1977, 46, 1.
35. Ziegler, T In Metal-Ligand Interactions: from Atoms, to Clusters, to Surfaces; Salahub, D. R.. Russo. N, Eds ; Kluwer Academic: Amsterdam, 1992.
36. (a) Snijders. J. G.: Baerends, E. J.; Vernoijs, P. At. Nucl. Data Tables 1982. 26. 483
37. (b) Vernoijs. P.; Snijders. J. G.; Baerends, E. J. Staler Type Basis Functions for the Whale Periodic System, Internal Report; Frije Universiteit, Amsterdam. 1981.
38. Krijn, J., Baerends, E. J. Fujunctions in the HFS Method, Internal Report: Frije Universiteit, Amsterdam. 1984.
39. Vosko, S. H.; Wilk, L.; Nusair, M Can. J. Phys. 1990, 55, 1200.
40. Becke, A. D. Phys. Rev. 1988, A38, 2938.
41. (a) Perdew, J. P., Phys. Rev. 1986, B33, 8822.
42. (b) Perdew, J. P. Phys. Rev. 1986, B34, 7406.
43. Chivers, T.; Parvez, M.; Zoricak, P. Unpublished results.
44. Carruthers, J. R.; Prout, K.; Watkin, D. J. Cryst. Struct. Commun. 1981, 10, 1217.
45. Allen, F. H.; Kennard, O.; Watson, D. G.; Brammer, L.; Orpen, A. G.; Taylor, R. J. Chem. Soc., Perkin Trans. 2 1987, S1.
46. Griller, D.; Martinho-Simöes, J. A.; Wagner, D. D. M. In Sulfur Centered Reactive Intermediates in Chemistry and Biology; Chatgilialoglu, C., Asmus, K. D.. Eds.; Plenum Press: New York, 1990.
47. (a) Miura, Y., Yamamoto, A.; Katsura, Y.; Kinoshita, M. J. Org. Chem. 1982. 47, 2618.
48. (b) Miura, Y.; Yamamoto, A. Katsura, Y.; Kinoshita, M. Bull. Chem Soc. Jpn. 1981, 54, 3215.
49. Levchenko, E. S.; Dubinina. T. N., Sereda, S. V : Antipin, M. Yu.; Struchkov, Yu. T ; Boldeskul, I. E. Zh. Org. Khim. 1987, 23, 86.
50. Lazar, M.; Rychly, J.; Klimo, V.; Pelikán,P.: Volko, L. Free Radicals in Chemistry and Biology; CRC Press: Boca Raton, FL. 1989: Chapter 3.
51. Mayer, R.; Decker, D.; Bleisch, S.; Domschke, G. J. Prakt. Chem. 1987, 329, 81.
52. (a) Negareche, M., Badrudin, Y.; Berchadsky, Y.; Friedmann, A.; Tordo, P. J. Org. Chem. 1986, 51, 342.
53. (b) Malatesta, V.; Ingold, K U. J. Am. Chem. Soc. 1973, 95, 6110.
54. (c) Lunazzi, L.; Ingold, K. U. J. Am. Chem. Soc. 1974, 96, 5558.
55. (d) Malatesta, V.; Ingold, K U. J. Am. Chem. Soc. 1974, 96, 3949.
56. (e) Malatesta, V., Lindsay, D.. Horseville, E. C.; Ingold, K. U. Can. J. Chem. 1974, 52, 864.
57. (a) Bonifacic, M.; Asmus, K.-D. J. Phys Chem. 1984, 88, 6286.
58. (b) Burkey, T. J.; Griller, D. J. Am. Chem. Soc. 1985, 707, 246.
59. (a) Laitinen, R.; Steudel, R.; Weiss, R. J. Chem. Soc., Dalton Turns. 1986, 1095.
60. (b) Minkwitz, R.; Gerhard, V.; Krause, R.; Prenzel, H ; Preut, H Z. Anorg. Allg. Chem. 1988, 559, 154.
61. (c) Minkwitz, R.; Krause, R.: Preut, H. Z. Anorg. Allg. Chem. 1989, 577, 133.
62. RUSS, C. R.; Douglass, I. B. In Sulfur in Organic and Inorganic Chemistry: Senning. A., Ed., Marcel Dekker: New York, 1971; p 248.
63. Raghavachari, K.: Haddon, R C. J. Phys. Chem. 1983, 87, 1312.