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Gas phase kinetic and theoretical studies of reactions of germylenes and dimethylstannylene

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Abstract

The results of time resolved gas phase studies of labile germylenes (GeH2 and GeMe2) and dimethylstannylene (SnMe2) reactions reported to date are considered together with data of quantum-chemical investigations of the potential energy surfaces of these systems. Reaction mechanisms are discussed. A comparison of reactivity in the series of carbene analogs, ER2 (E = Si, Ge, Sn, R = H, Me), is made.

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References

  1. O. M. Nefedov and M. N. Manakow, Angew. Chem., 1966, 78, 1966.

    Google Scholar 

  2. O. M. Nefedov, A. I. Ioffe, and L. G. Menchikov, Chemistry of Carbenes, Moscow, Khimiya, 1990.

    Google Scholar 

  3. P. P. Gaspar and R. West, in The chemistry of organic silicon compounds, Eds Z. Rappoport and Y. Apeloig, J. Wiley and Sons Ltd, Chichester, V. 2, 1998, 2463.

    Google Scholar 

  4. W. P. Neumann, Chem. Rev, 1991, 91, 311.

    Article  Google Scholar 

  5. M. P. Egorov and P. P. Gaspar, Germanium, organometallic chemistry, the encyclopedia of inorganic chemistry, Ed. R. B. King, J. Wiley and Sons, New York, 1995, 3, 1229.

    Google Scholar 

  6. O. M. Nefedov, M. P. Egorov, A. I. Ioffe, L. G. Menchikov, P. S. Zuev, V. I. Minkin, B. Ya. Simkin, and M. N. Glukhovtsev, Pure Appl. Chem., 1992, 64, 265.

    Google Scholar 

  7. S. E. Boganov; M. P. Egorov, V. I. Faustov, and O. M. Nefedov, in The chemistry of organic germanium, tin and lead compounds, Ed. Z. Rappoport, Wiley, 2002, V. 2, Part 1, 749.

  8. I. Safarik, V. Sandhu, E. M. Lown, O. P. Strausz, and T. N. Bell, Research on Chem. Intermediates., 1990, 14, 105.

    Google Scholar 

  9. J. M. Jasinski, R. Becerra, and R. Walsh, Chem. Rev., 1995, 95, 1203

    Article  Google Scholar 

  10. R. Becerra and R. Walsh, in Research in Chemical Kinetics, Eds R. G. Compton and G. Hancock, Elsevier, Amsterdam, 1995, V. 3, p. 263.

    Google Scholar 

  11. M. P. Egorov, A. S. Dvornikov, V. A. Kuzmin, S. P. Kolesnikov, and O. M. Nefedov, Izv. Akad. Nauk SSSR, Ser. Khim., 1987, 1200 [Bull. Acad. Sci. USSR, Div. Chem. Sci., 1987, 36, 1114 (Engl. Transl.)].

  12. K. Mochida, M. Wakasa, Y. Nakadira, Y. Sakaguchi, and H. Hayashi, Organometallics, 1988, 7, 1869.

    Article  Google Scholar 

  13. S. P. Kolesnikov, M. P. Egorov, A. S. Dvornikov, V. A. Kuzmin, and O. M. Nefedov, Metalloorg. Khim., 1989, 2, 799 [Organomet. Chem. USSR, 1989, 2 (Engl. Transl.)].

    Google Scholar 

  14. M. Wakasa, I. Yoneda, and K. Mochida, J. Organometal. Chem., 1989, 366, C1.

    Article  Google Scholar 

  15. K. Mochida, I. Yoneda, and M. Wakasa, J. Organometal. Chem., 1990, 399, 53.

    Article  Google Scholar 

  16. K. L. Bobbitt, V. M. Maloney, and P. P. Gaspar, Organometallics, 1991, 10, 2772.

    Article  Google Scholar 

  17. K. Mochida, N. Kanno, R. Kato, M. Kotani, S. Yamauchi, M. Wakasa, and H. Hayasi, J. Organometal. Chem., 1991, 415, 191.

    Article  Google Scholar 

  18. K. Mochida and S. Tokura, Bull. Chem. Soc. Jpn., 1992, 65, 1642.

    Google Scholar 

  19. K. Mochida, K. Kimijima, H. Chiba, M. Wakasa, and H. Hiyashi, Organometallics, 1994, 13, 404.

    Article  Google Scholar 

  20. S. Konieczny, S. J. Jacobs, J. K. Wilking, and P. P. Gaspar, J. Organometal. Chem., 1988, 341, C17.

    Article  Google Scholar 

  21. N. P. Toltl, W. J. Leigh, G. M. Kollegger, W. G. Stibbs, and K. M. Baines, Organometallics, 1996, 15, 3732.

    Article  Google Scholar 

  22. K. Mochida, S. Tokura, and S. Murata, J. Chem. Soc., Chem. Comm., 1992, 250.

  23. R. Becerra, S. E. Boganov, M. P. Egorov, O. M. Nefedov, and R. Walsh, Chem. Phys. Lett., 1996, 260, 433.

    Article  Google Scholar 

  24. U. A. Alexander, N. A. Trout, K. D. King, and W. D. Lawrance, Chem. Phys. Lett., 1999, 299, 291.

    Article  Google Scholar 

  25. R. Becerra, S. E. Boganov, M. P. Egorov, V. Ya. Lee, O. M. Nefedov, and R. Walsh, Chem. Phys. Lett., 1996, 250, 111.

    Article  Google Scholar 

  26. R. Becerra, M. P. Egorov, I. V. Krylova, O. M. Nefedov, and R. Walsh, Chem. Phys. Lett., 2002, 351, 47.

    Article  Google Scholar 

  27. J. E. Baggott, M. A. Blitz, H. M. Frey, P. D. Lightfoot, and R. Walsh, Chem. Phys. Lett., 1987, 135, 39.

    Article  Google Scholar 

  28. E. C.-L. Ma, D. P. Paquin, and P. P. Gaspar, J. Chem. Soc., Chem. Comm., 1980, 381.

  29. E. C.-L. Ma, K. Kobayashi, M. W. Barzilai, and P. P. Gaspar, J. Organomet. Chem., 1982, 224, C13.

    Article  Google Scholar 

  30. D. Lei and P. P. Gaspar, Polyhedron, 1991, 10, 1221.

    Article  Google Scholar 

  31. W. Du, L. A. Keeling, and C. M. Greenlief, J. Vac. Sci. Technol. A, 1994, 12, 2281.

    Article  Google Scholar 

  32. C. Isobe, H. Cho, and J. E. Crowell, Surf. Sci., 1993, 295, 117.

    Article  Google Scholar 

  33. H. Simka, M. Hierlemann, M. Utz, and K. F. Jensen, J. Electrochem. Soc., 1996, 143, 2646.

    Google Scholar 

  34. C. G. Newman, J. Dzarnoski, M. A. Ring, and H. E. O’Neal, Int. J. Chem. Kinet., 1980, 12, 661.

    Article  Google Scholar 

  35. R. Becerra, S. E. Boganov, M. P. Egorov, V. I. Faustov, O. M. Nefedov, and R. Walsh, J. Am. Chem. Soc., 1998, 120, 12657.

    Article  Google Scholar 

  36. K. Saito and K. Obi, Chem. Phys. Lett., 1993, 215, 193.

    Article  Google Scholar 

  37. K. Obi, M. Fukushima, and K. Saito, Appl. Surf. Sci., 1994, 79/80, 465.

    Article  Google Scholar 

  38. K. Saito and K. Obi, Chem. Phys., 1994, 187, 381.

    Article  Google Scholar 

  39. J. Karolczak, W. P. Harper, R. S. Grev, and D. J. Clouthier, J. Chem. Phys., 1995, 103, 2839.

    Article  Google Scholar 

  40. A. Campargue and R. Escribano, Chem. Phys. Lett., 1999, 315, 397.

    Article  Google Scholar 

  41. W. J. Leigh, C. R. Harrington, and I. Vargas-Baca, J. Am. Chem. Soc., 2004, 126, 16105.

    Article  PubMed  Google Scholar 

  42. J. M. Jasinski, B. S. Meyerson, and B. A. Scott, Annu. Rev. Phys. Chem., 1987, 38, 109.

    Article  Google Scholar 

  43. G. Lu and J. E. Crowell, J. Chem. Phys., 1993, 98, 3415.

    Article  Google Scholar 

  44. P. P. Gaspar, C. A. Levy, J. J. Frost, and S. A. Bock, J. Am. Chem. Soc., 1969, 91, 1573.

    Article  Google Scholar 

  45. P. Estacio, M. D. Sefcik, E. K. Chan, and M. A. Ring, Inorg. Chem., 1970, 9, 1068.

    Article  Google Scholar 

  46. M. D. Sefcik and M. A. Ring, J. Organomet. Chem., 1973, 59, 167.

    Article  Google Scholar 

  47. R. Becerra, I. V. Krylova, M. P. Egorov, O. M. Nefedov and R. Walsh, VII Conf. “Chemistry of Carbenes and Related Intermediates” (Kazan, June 23–26, 2003), Abstrs, Kazan, 2003, p. 73.

  48. J. E. Baggott, M. A. Blitz, H. M. Frey, and R. Walsh, J. Am. Chem. Soc., 1990, 112, 8337.

    Article  Google Scholar 

  49. J. E. Baggott, H. M. Frey, P. D. Lightfoot, R. Walsh, and I. M. Watts, J. Chem. Soc., Faraday Trans., 1990, 86, 27.

    Google Scholar 

  50. R. Becerra, S. E. Boganov, M. P. Egorov, V. I. Faustov, O. M. Nefedov, and R. Walsh, Phys. Chem. Chem. Phys., 2001, 3, 184.

    Article  Google Scholar 

  51. R. Becerra, S. E. Boganov, M. P. Egorov, O. M. Nefedov, and R. Walsh, Mendeleev Commun., 1997, 87.

  52. R. Becerra and R. Walsh, Phys. Chem. Chem. Phys., 1999, 1, 5301.

    Article  Google Scholar 

  53. U. N. Alexander, K. D. King, and W. D. Lawrance, Chem. Phys. Lett., 2000, 319, 529.

    Article  Google Scholar 

  54. R. Becerra, H. M. Frey, B. P. Mason, R. Walsh, and M. S. Gordon, J. Chem. Soc., Faraday Trans., 1995, 91, 2723.

    Google Scholar 

  55. R. Becerra, S. Boganov, and R. Walsh, J. Chem. Soc., Faraday Trans., 1998, 94, 3569.

    Google Scholar 

  56. I. W. Carpenter, PhD Thesis, University of Reading, 1996.

  57. J. Troe, J. Chem. Soc., Faraday Trans., 1994, 90, 2303.

    Google Scholar 

  58. G. Trinquier, J. Chem. Soc., Faraday Trans., 1993, 89, 775.

    Google Scholar 

  59. R. Becerra, H. M. Frey, B. P. Mason, and R. Walsh, J. Chem. Soc., Faraday Trans., 1993, 89, 411.

    Google Scholar 

  60. P. N. Noble and R. Walsh, Int. J. Chem. Kinet., 1983, 15, 547.

    Article  Google Scholar 

  61. R. Becerra and R. Walsh, Int. J. Chem. Kinet., 1999, 31, 393.

    Article  Google Scholar 

  62. R. Walsh, Pure Appl. Chem., 1987, 59, 69.

    Google Scholar 

  63. R. Becerra and R. Walsh, Thermochemistry, in The Chemistry of Organosilicon Compounds, Eds Z. Rappoport and Y. Apeloig, Wiley, Chichester, 1998, V. 2, Chapt. 4, p. 153.

    Google Scholar 

  64. J. E. Baggott, M. A. Blitz, H. M. Frey, P. D. Lightfoot, and R. Walsh, Int. J. Chem. Kinet., 1992, 24, 127.

    Article  Google Scholar 

  65. U. N. Alexander, K. D. King, and W. D. Lawrance, Phys. Chem. Chem. Phys., 2001, 3, 3085.

    Article  Google Scholar 

  66. M. W. Heaven, G. F. Metha, and M. A. Buntine, J. Phys. Chem., A, 2001, 105, 1185.

    Google Scholar 

  67. S. Su and M. S. Gordon, Chem. Phys. Lett., 1993, 204, 306.

    Article  Google Scholar 

  68. R. Becerra, S. E. Boganov, M. P. Egorov, V. I. Faustov, O. M. Nefedov, and R. Walsh, Can. J. Chem., 2000, 78, 1428.

    Article  Google Scholar 

  69. J. M. Jasinski, J. Phys. Chem., 1986, 90, 555.

    Article  Google Scholar 

  70. M. S. Gordon, D. R. Gano, J. S. Binkley, and M. J. Frisch, J. Am. Chem. Soc., 1986, 108, 2191.

    Article  Google Scholar 

  71. R. L. Jenkins, R. A. Kedrowski, L. E. Elliot, D. C. Tappen, D. J. Schlyer, and M. A. Ring, J. Organomet. Chem., 1975, 86, 347.

    Article  Google Scholar 

  72. R. Becerra, S. E. Boganov, M. P. Egorov, V. I. Faustov, V. M. Promyslov, O. M. Nefedov, and R. Walsh, Phys. Chem. Chem. Phys., 2002, 4, 5079.

    Article  Google Scholar 

  73. R. Becerra and R. Walsh, Phys. Chem. Chem. Phys., 2002, 4, 6001.

    Article  Google Scholar 

  74. R. Becerra and R. Walsh, J. Organomet. Chem., 2001, 636, 49.

    Article  Google Scholar 

  75. R. Becerra, S. E. Boganov, M. P. Egorov, V. I. Faustov, I. V. Krylova, O. M. Nefedov, V. M. Promyslov, and R. Walsh, Phys. Chem. Chem. Phys., 2004, 6, 3370.

    Article  Google Scholar 

  76. N. Al-Rubaiey and R. Walsh, J. Phys. Chem., 1994, 98, 5303.

    Article  Google Scholar 

  77. N. Al-Rubaiey, R. Becerra, and R. Walsh, Phys. Chem. Chem. Phys., 2002, 4, 5072.

    Article  Google Scholar 

  78. N. Al-Rubaiey, I. W. Carpenter, R. Walsh, R. Becerra, and M. S. Gordon, J. Phys. Chem., A, 1998, 102, 8564.

    Google Scholar 

  79. R. Becerra, H. M. Frey, B. P. Mason, and R. Walsh, J. Chem. Soc., Chem. Commun., 1993, 1050.

  80. R. Becerra and R. Walsh, Int. J. Chem. Kinet., 1994, 26, 45.

    Article  Google Scholar 

  81. R. Becerra, J. P. Cannady, and R. Walsh, Phys. Chem. Chem. Phys., 2001, 3, 2343.

    Article  Google Scholar 

  82. R. Becerra, J. P. Cannady, and R. Walsh, J. Chem. Phys A., 2002, 106, 11558.

    Article  Google Scholar 

  83. P. Antoniotti, P Benzi, M. Castiglioni, and P. Volpe, Eur. J. Inorg. Chem. 1999, 323.

  84. S. Sakai, Int. J. Quantum Chem., 1998, 70, 291.

    Article  Google Scholar 

  85. M.-D. Su and S.-Y. Chu, J. Am. Chem. Soc., 1999, 121, 11478.

    Article  Google Scholar 

  86. D. A. Horner, R. S. Grev, and H. F. Schaefer III, J. Am. Chem. Soc., 1992, 114, 2093.

    Article  Google Scholar 

  87. W. Ando, H. Ohgaki, and Y. Kabe, Angew. Chem. Int. Ed. Engl., 1994, 33, 659.

    Article  Google Scholar 

  88. H. Ohgaki, Y. Kabe, and W. Ando, Organometallics, 1995, 14, 2139.

    Article  Google Scholar 

  89. P. N. Skancke, D. A. Hrovat, and W. T. Borden, J. Am. Chem. Soc., 1997, 119, 8012.

    Article  Google Scholar 

  90. V. N. Khabashesku, K. N. Kudin, J. Tamas, S. E. Boganov, J. L. Margrave, and O. M. Nefedov, J. Am. Chem. Soc., 1998, 120, 5005.

    Article  Google Scholar 

  91. V. N. Khabashesku, S. E. Boganov, K. N. Kudin, J. L. Margrave, J. Michl, and O. M. Nefedov, Russ. Chem. Bull., 1999, 48, 2003.

    Google Scholar 

  92. F. Anwari and M. S. Gordon, Isr. J. Chem., 1983, 23, 129.

    Google Scholar 

  93. A. D. Krebs and J. Berndt, Tetrahedron Lett., 1983, 24, 4083.

    Article  Google Scholar 

  94. M. P. Egorov, S. P. Kolesnikov, Yu. T. Struchkov, M. Yu. Antipin, S. V. Sereda, and O. M. Nefedov, J. Organometal. Chem., 1985, 290, C27.

    Article  Google Scholar 

  95. M. T. Nguyen, D. Sengupta, and L. G. Vanquickenborne, Chem. Phys. Lett., 1995, 240, 513.

    Article  Google Scholar 

  96. P. N. Skancke, D. A. Hrovat, and W. T. Borden, J. Phys. Chem. A, 1999, 103, 4043.

    Article  Google Scholar 

  97. G. Maier, H. P. Reisenauer, and H. Egenolf, Eur. J. Org. Chem., 1998, 1313.

  98. K. A. Holbrook, M. J. Pilling, and S. H. Robertson, Unimolecular Reactions, Wiley, Chichester, 2nd edn., 1996.

    Google Scholar 

  99. J. W. Davies and M. J. Pilling, in Advances in Gas Phase Photochemistry and Kinetics, Eds M. N. R. Ashfold and J. E. Baggott, Royal Society of Chemistry, London, 1989, vol. 2, Chapt. 3, p. 105.

    Google Scholar 

  100. U. N. Alexander, K. D. King, and W. D. Lawrance, Phys. Chem. Chem. Phys., 2003, 5, 1557.

    Article  Google Scholar 

  101. U. N. Alexander, K. D. King, and W. D. Lawrance, J. Phys. Chem. A, 2002, 106, 973.

    Article  Google Scholar 

  102. R. Becerra, J. P. Cannady, and R. Walsh, J. Phys. Chem. A, 2003, 107, 11049.

    Article  Google Scholar 

  103. M. W. Heaven, G. F. Metha, and M. A. Buntine, Aust. J. Chem., 2001, 54, 185.

    Article  Google Scholar 

  104. R. Becerra, I. W. Carpenter, G. J. Gutsche, K. D. King, W. D. Lawrance, W. S. Staker, and R. Walsh, Chem. Phys. Lett., 2001, 333, 83.

    Article  Google Scholar 

  105. S. R. Gunn and L. G. Green, J. Phys. Chem., 1961, 65, 779.

    Google Scholar 

  106. S. R. Gunn and J. H. Kindsvater, J. Phys. Chem., 1966, 70, 1750.

    Google Scholar 

  107. M. J. Almond, A. M. Doncaster, P. N. Noble, and R. Walsh, J. Am. Chem. Soc., 1982, 104, 4717.

    Article  Google Scholar 

  108. P. N. Noble and R. Walsh, Int. J. Chem. Kinet., 1983, 15, 547.

    Article  Google Scholar 

  109. B. Ruscic, M. Schwartz, and J. Berkowitz, J. Chem. Phys., 1990, 92, 1865.

    Article  Google Scholar 

  110. W. E. Dasent, Nonexistent Compounds, Arnold, London, 1965, Chapt. 5, p. 77.

    Google Scholar 

  111. S. W. Benson, Thermochemical Kinetics, Wiley, New York, 2nd edn., 1976.

    Google Scholar 

  112. J. A. Boatz and M. S. Gordon, J. Phys. Chem., 1989, 93, 3025.

    Article  Google Scholar 

  113. J. A. Boatz, M. S. Gordon, and L. R. Sita, J. Phys. Chem., 1990, 94, 5488.

    Article  Google Scholar 

  114. A. M. Doncaster and R. Walsh, J. Phys. Chem., 1979, 83, 578.

    Article  Google Scholar 

  115. L. H. Long and C. I. Pulford, J. Chem. Soc., Faraday Trans., 1986, 82, 567.

    Google Scholar 

  116. R. Becerra, S. E. Boganov, M. P. Egorov, V. I. Faustov, I. V. Krylova, O. M. Nefedov, and R. Walsh, J. Am. Chem. Soc., 2002, 124, 7555.

    Article  PubMed  Google Scholar 

  117. L. R. Sita and R. D. Bickerstaff, Phosphorus, Sulfur Silicon Relat. Elem., 1989, 41, 31.

    Google Scholar 

  118. J. P. Cotton, P. J. Davidson, M. F. Lappert, J. Chem. Soc., Dalton Trans., 1976, 2275.

  119. U. N. Alexander, Ph. D. Thesis, Flinders University of South Australia, 2000.

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Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 3, pp. 477–505, March, 2005.

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Boganov, S.E., Egorov, M.P., Faustov, V.I. et al. Gas phase kinetic and theoretical studies of reactions of germylenes and dimethylstannylene. Russ Chem Bull 54, 483–511 (2005). https://doi.org/10.1007/s11172-005-0285-5

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