Isolation and structural characterization of some aryltellurium halides and their hydrolyzed products stabilized by an intramolecular Te⋯N interaction

Organometallics

Volumn 30, Issue 3, 2011, Pages 534-546

  Srivastava, Kriti ^a   Shah, Poonam ^a   Singh, Harkesh B ^a   Butcher, Ray J ^b  

^a INDIAN INSTITUTE OF TECHNOLOGY BOMBAY   (India)

^b HOWARD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALINE HYDROLYSIS; ALKALINE SOLUTIONS; CO-CRYSTALS; ELEMENTAL ANALYSIS; FTIR SPECTROSCOPY; HYDRAZINE HYDRATE; HYDROLYZED PRODUCTS; MIXED-VALENT; MULTINUCLEAR NMR; ORTHO-LITHIATION; OXIDATIVE ADDITIONS; REFLUX CONDITIONS; SODIUM SALT; STRUCTURAL CHARACTERIZATION; TELLURIUM OXIDE; TRANSMETALATION; TRIIODIDE;

CHLORINE COMPOUNDS; DENSITY FUNCTIONAL THEORY; HYDRATES; HYDROLYSIS; MERCURY (METAL); MERCURY COMPOUNDS; TELLURIUM; X RAY CRYSTALLOGRAPHY;

TELLURIUM COMPOUNDS;

EID: 79751491695     PISSN: 02767333     EISSN: 15206041     Source Type: Journal    
DOI: 10.1021/om1009022     Document Type: Article

References (89)

1. Lederer, K. Ann. Chem. 1912, 391, 326
2. Morgan, G. T.; Kellett, R. E. J. Chem. Soc. 1926, 129, 1080
3. Lederer, K. Chem. Ber. 1916, 49, 1076
4. Bergman, J. Tetrahedron 1972, 28, 3323
5. Thavornyutikarn, P.; McWhinnie, W. R. J. Organomet. Chem. 1973, 50, 135 and references therein
6. Irgolic, K. I. The Organic Chemistry of Tellurium; Gordon and Breach: New York, 1974.
7. Alcock, N. W.; Harrison, W. D. J. Chem. Soc., Dalton Trans. 1982, 709
8. Beckmann, J.; Dakternieks, D.; Duthie, A.; Ribot, F.; Schürmann, M.; Lewcenko, N. A. Organometallics 2003, 22, 3257
9. Beckmann, J.; Finke, P.; Hesse, M.; Wettig, B. Angew. Chem., Int. Ed. 2008, 120, 10130
10. Beckmann, J.; Bolsinger, J.; Finke, P.; Hesse, M. Angew. Chem., Int. Ed. 2010, 49, 8030
11. Ley, S. V.; Meerholz, C. A.; Barton, D. H. R. Tetrahedron Lett. 1980, 21, 1785
12. Engman, L.; Cava, M. P. Tetrahedron Lett. 1981, 22, 5251
13. Akiba, M.; Lakshmikantham, M. V.; Jen, K.-Y.; Cava, M. P. J. Org. Chem. 1984, 49, 4819
14. Barton, D. H. R.; Finet, J.-P.; Thomas, M. Tetrahedron 1986, 42, 2319
15. Xue, M.; Gao, Y.-C.; Shen, J.-K.; Shi, Q.-Z.; Basolo, F. Inorg. Chim. Acta 1993, 207, 207
16. Liu, X.; Gao, Y.-C.; Su, Z.-X.; Wang, Y.-Y.; Shi, Q.-Z. Transition Met. Chem. 1999, 24, 666
17. Song, L.-C.; Li, Q.-S.; Hu, Q.-M.; Dong, Y.-B. J. Organomet. Chem. 2001, 619, 194
18. Huang, Z.-Z.; Tang, Y. J. Org. Chem. 2002, 67, 5320
19. Oba, M.; Okada, Y.; Nishiyama, K.; Sihmada, S.; Ando, W. Chem. Commun. 2008, 5378
20. Citeau, H.; Kirschbaum, K.; Conrad, O.; Giolando, D. M. Chem. Commun. 2001, 2006
21. Sadekov, I. D.; Maksimenko, A. A.; Maslakov, A. G.; Minkin, V. I. J. Organomet. Chem. 1990, 391, 179
22. Naumann, D.; Tyrra, W.; Herrmann, R.; Pantenburg, I.; Wickleder, M. S. Z. Anorg. Allg. Chem. 2002, 628, 833
23. Klapötke, T. M.; Krumm, B.; Mayer, P.; Piotrowski, H.; Ruscitti, O. P. Z. Naturforsch. 2002, B57, 145
24. Kobayashi, K.; Deguchi, N.; Takahashi, O.; Tanaka, K.; Horn, E.; Kikuchi, O.; Furukawa, N. Angew. Chem., Int. Ed. 1999, 38, 1638
25. Kobayashi, K.; Tanaka, K.; Izawa, H.; Arai, Y.; Furukawa, N. Chem. Eur. J. 2001, 7, 4272
26. Kobayashi, K.; Izawa, H.; Yamaguchi, K.; Horn, E.; Furukawa, N. Chem. Commun. 2001, 1428
27. Beckmann, J.; Dakternieks, D.; Duthie, A.; Lewcenko, N. A.; Mitchell, C. Angew. Chem., Int. Ed. 2004, 43, 6683
28. Dong, Z.; Li, X.; Liang, K.; Mao, S.; Huang, X.; Yang, B.; Xu, J.; Liu, J.; Luo, G.; Shen, J. J. Org. Chem. 2007, 72, 606
29. Hamor, T. A.; Al-Salim, N.; West, A. A.; McWhinnie, W. R. J. Organomet. Chem. 1986, 310, C5
30. Kaur, R.; Singh, H. B.; Butcher, R. J. Organometallics 1995, 14, 4755
31. Poleschner, H.; Seppelt, K. Chem. Eur. J. 2004, 10, 6565
32. Wismach, C.; du Mont, W.-W.; Jones, P. G.; Ernst, L.; Papke, U.; Mugesh, G.; Kaim, W.; Wanner, M.; Becker, K. D. Angew. Chem., Int. Ed. 2004, 43, 3970
33. Kumar, S.; Kandasamy, K.; Singh, H. B.; Wolmershäuser, G.; Butcher, R. J. Organometallics 2004, 23, 4199
34. Kulcsar, M.; Silvestru, A.; Silvestru, C.; Drake, J. E.; Macdonald, C. L. B.; Hursthouse, M. E.; Light, M. E. J. Organomet. Chem. 2005, 690, 3217
35. Beckmann, J.; Bolsinger, J.; Duthie, A. Organometallics 2009, 28, 4610
36. Srivastava, K.; Sharma, S.; Singh, H. B.; Singh, U. P.; Butcher, R. J. Chem. Commun. 2010, 46, 1130
37. Ahmed, M. A. K.; McWhinnie, W. R.; Hamor, T. A. J. Organomet. Chem. 1985, 293, 219
38. Ahmed, M. A. K.; McCarthy, A. E.; McWhinnie, W. R.; Berry, F. J. J. Chem. Soc., Dalton Trans. 1986, 771
39. Abid, K. Y.; Al-Salim, N. I.; Greaves, M.; McWhinnie, W. R.; West, A. A.; Hamor, T. A. J. Chem. Soc., Dalton Trans. 1989, 1697
40. Majeed, Z.; McWhinnie, W. R.; Hamor, T. A. J. Organomet. Chem. 1997, 549, 257
41. Cobbledick, R. E.; Einstein, F. W. B.; McWhinnie, W. R.; Musa, F. H. J. Chem. Res., Synop. 1979, 145
42. Roling, P. V.; Kirt, D. D.; Dill, J. L.; Hall, S.; Hollstrom, C. J. Organomet. Chem. 1976, 116, 39
43. Roling, P. V. J. Org. Chem. 1975, 40, 2421
44. Ahmed, M. A. K.; McWhinnie, W. R.; Hamor, T. A. J. Organomet. Chem. 1985, 281, 205
45. Brauer, G. Handbook of Preparative Inorganic Chemistry, 3 rd ed.; Academic Press: New York, 1975.
46. Detty, M. R.; Friedman, A. E.; McMillan, M. Organometallics 1995, 14, 1442
47. Detty, M. R.; Williams, A. J.; Hewitt, J. M.; McMillan, M. Organometallics 1995, 14, 5258
48. Kumar, S.; Helt, J.-C. P.; Autschbach, J.; Detty, M. R. Organometallics 2009, 28, 3426
49. Minkin, V. I.; Sadekov, I. D.; Maksimenko, A. A.; Kompan, O. E.; Struchkov, Y. T. J. Organomet. Chem. 1991, 402, 331 and references therein
50. Apte, S. D.; Singh, H. B.; Butcher, R. J. J. Chem. Res., Synop. 2000, 160; J. Chem. Res., Miniprint 2000, 559.
51. Beckmann, J.; Hesse, M.; Poleschner, H.; Seppelt, K. Angew. Chem., Int. Ed. 2007, 46, 8277
52. Menon, S. C.; Singh, H. B.; Patel, R. P.; Das, K.; Butcher, R. J. Organometallics 1997, 16, 563
53. Klapötke, T. M.; Krumm, B.; Mayer, P.; Polborn, K.; Ruscitti, O. P. Inorg. Chem. 2001, 40, 5169
54. Klapötke, T. M.; Krumm, B.; Mayer, P.; Piotrowski, H.; Ruscitti, O. P. Z. Anorg. Allg. Chem. 2002, 628, 229
55. Beckmann, J.; Dakternieks, D.; Duthie, A.; Smith, N. A. J. Organomet. Chem. 2003, 669, 149
56. Kandasamy, K.; Kumar, S.; Singh, H. B.; Wolmershäuser, G. Organometallics 2003, 22, 5069
57. Chauhan, A. K. S.; Anamika; Kumar, A.; Srivastava, R. C.; Butcher, R. J.; Duthie, A. J. Organomet. Chem. 2006, 691, 5887
58. Amosova, S. V.; Martynov, A. V.; Shagun, V. A.; Musalov, M. V.; Larina, L. I.; Krivdin, L. B.; Zhilitskaya, L. V.; Voronkov, M. G. J. Organomet. Chem. 2008, 693, 2509
59. Al-Salim, N.; West, A. A.; McWhinnie, W. R.; Hamor, T. A. J. Chem. Soc., Dalton Trans. 1988, 2363
60. Bondi, A. J. Phys. Chem. 1964, 68, 441
61. Chao, G. Y.; McCullough, J. D. Acta Crystallogr. 1962, 15, 887
62. Pauling, L. The Nature of the Chemical Bond, 3 rd ed.; Cornell University Press: Ithaca, NY, 1960.
63. Chauhan, A. K. S.; Anamika; Kumar, A.; Srivastava, R. C.; Butcher, R. J.; Beckmann, J.; Duthie, A. J. Organomet. Chem. 2005, 690, 1350
64. Wu, Y.; Ding, K.; Wang, Y.; Zhu, Y.; Yang, L. J. Organomet. Chem. 1994, 468, 13
65. Laitalainen, T.; Sundberg, M. R.; Uggla, R.; Bergman, J. Polyhedron 1997, 16, 2441
66. Niyomura, O.; Kato, S.; Inagaki, S. J. Am. Chem. Soc. 2000, 122, 2132
67. Chauhan, A. K. S.; Kumar, A.; Srivastava, R. C.; Butcher, R. J. J. Organomet. Chem. 2002, 658, 169
68. Chauhan, A. K. S.; Singh, P.; Kumar, A.; Srivastava, R. C.; Butcher, R. J.; Duthie, A. Organometallics 2007, 26, 1955
69. Chauhan, A. K. S.; Singh, P.; Srivastava, R. C.; Duthie, A.; Voda, A. Dalton Trans. 2008, 4023
70. Chauhan, A. K. S.; Kumar, A.; Srivastava, R. C.; Beckmann, J.; Duthie, A.; Butcher, R. J. J. Organomet. Chem. 2004, 689, 345
71. Bakshi, P. K.; Cameron, T. S.; Ali, M. E. S.; Malik, M. A.; Smith, B. C. Inorg. Chim. Acta 1993, 204, 27
72. Alcock, N. W.; Harrison, W. D. J. Chem. Soc., Dalton Trans. 1984, 869
73. Farran, J.; Alvarez-Larena, A.; Capparelli, M. V.; Piniella, J. F.; Germain, G.; Torres-Castellanos, L. Acta Crystallogr. 1998, C54, 995
74. Lang, E. S.; Fernandes, R. M., Jr; Silveira, E. T.; Abram, U.; Vázquez-López, E. M. Z. Anorg. Allg. Chem. 1999, 625, 1401
75. This stoichiometry was initially established by refining the occupancy of this partial Na (Na1) and restraining the thermal parameters of the two Na atoms (Na1 and Na2) to be similar. As the occupancy of Na1 was refined to a value very close to 0.50, it was fixed at this value for future calculations, as otherwise the occupancy and thermal parameters of this atom are highly correlated. Around Na1 there are disordered water molecules which fill the vacancy when this position is not occupied by the sodium cation and the species is in the acid form. In the tellurinic acid anion the two O atoms are disordered with occupancies of 0.569(4) and 0.431(4), while in the tellurinic acid/salt cocrystal one of the O positions is fully occupied and the other is disordered over two positions (O-H and O for the acid and salt anion, respectively), each with 50% occupancy. The proton attached to O2AA was found in the difference Fourier at an appropriate O-H distance and Te-O-H angle and had a normal hydrogen bond to O2WA.
76. Kennedy, A. R.; Andrikopoulos, P. C.; Arlin, J.-B.; Armstrong, D. R.; Duxbury, N.; Graham, D. V.; Kirkhouse, J. B. A. Chem. Eur. J. 2009, 15, 9494
77. Rozantsev, G. M.; Radio, S. V.; Gumerova, N. I.; Baumer, V. N.; Shishkin, O. B. J. Struct. Chem. 2009, 50, 296
78. Shen, L.; Xu, Y.-Q.; Gao, Y.-Z.; Cui, F.-Y.; Hu, C.-W. J. Mol. Struct. 2009, 934, 37
79. Fujihara, H.; Tanaka, H.; Furukawa, N. J. Chem. Soc., Perkin Trans. 2 1995, 2375
80. Alcock, N. W.; Harrison, W. D.; Howes, C. J. Chem. Soc., Dalton Trans. 1984, 1709
81. Chandrasekhar, V.; Kumar, A. J. Organomet. Chem. 2009, 694, 2628
82. Mancinelli, C. S.; Titus, D. D.; Ziolo, R. F. J. Organomet. Chem. 1977, 140, 113
83. Magnus, P.; Roe, M. B.; Lynch, V.; Hulme, C. J. Chem. Soc., Chem. Commun. 1995, 1609
84. Beckmann, J.; Dakternieks, D.; Duthie, A.; Lewcenko, N. A.; Mitchell, C.; Schürmann, M. Z. Anorg. Allg. Chem. 2005, 631, 1856
85. Klapötke, T. M.; Krumm, B.; Mayer, P.; Polborn, K.; Schwab, I. Z. Anorg. Allg. Chem. 2005, 631, 2677
86. Geometry optimization were performed at the B3LYP/6-311G(d,p) level for H, C, N, O and at the Lanl2dz(d,p) level for Te using the Gaussian 03 software package. (see the Supporting Information for details): Frisch, M. J. Gaussian 03, revision C.02; Gaussian, Inc., Wallingford, CT, 2004.
87. Reed, A. E.; Curtiss, L. A.; Weinhold, F. Chem. Rev. 1988, 88, 899
88. Glendening, E. D.; Reed, A. E.; Carpenter, J. E.; Weinhold, F. NBO Version 3.1.
89. Bader, R. F. W. Atoms in Molecules: A Quantum Theory; Oxford University Press: New York, 1990.