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.
Similar content being viewed by others
References
O. M. Nefedov and M. N. Manakow, Angew. Chem., 1966, 78, 1966.
O. M. Nefedov, A. I. Ioffe, and L. G. Menchikov, Chemistry of Carbenes, Moscow, Khimiya, 1990.
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.
W. P. Neumann, Chem. Rev, 1991, 91, 311.
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.
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.
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.
I. Safarik, V. Sandhu, E. M. Lown, O. P. Strausz, and T. N. Bell, Research on Chem. Intermediates., 1990, 14, 105.
J. M. Jasinski, R. Becerra, and R. Walsh, Chem. Rev., 1995, 95, 1203
R. Becerra and R. Walsh, in Research in Chemical Kinetics, Eds R. G. Compton and G. Hancock, Elsevier, Amsterdam, 1995, V. 3, p. 263.
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.)].
K. Mochida, M. Wakasa, Y. Nakadira, Y. Sakaguchi, and H. Hayashi, Organometallics, 1988, 7, 1869.
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.)].
M. Wakasa, I. Yoneda, and K. Mochida, J. Organometal. Chem., 1989, 366, C1.
K. Mochida, I. Yoneda, and M. Wakasa, J. Organometal. Chem., 1990, 399, 53.
K. L. Bobbitt, V. M. Maloney, and P. P. Gaspar, Organometallics, 1991, 10, 2772.
K. Mochida, N. Kanno, R. Kato, M. Kotani, S. Yamauchi, M. Wakasa, and H. Hayasi, J. Organometal. Chem., 1991, 415, 191.
K. Mochida and S. Tokura, Bull. Chem. Soc. Jpn., 1992, 65, 1642.
K. Mochida, K. Kimijima, H. Chiba, M. Wakasa, and H. Hiyashi, Organometallics, 1994, 13, 404.
S. Konieczny, S. J. Jacobs, J. K. Wilking, and P. P. Gaspar, J. Organometal. Chem., 1988, 341, C17.
N. P. Toltl, W. J. Leigh, G. M. Kollegger, W. G. Stibbs, and K. M. Baines, Organometallics, 1996, 15, 3732.
K. Mochida, S. Tokura, and S. Murata, J. Chem. Soc., Chem. Comm., 1992, 250.
R. Becerra, S. E. Boganov, M. P. Egorov, O. M. Nefedov, and R. Walsh, Chem. Phys. Lett., 1996, 260, 433.
U. A. Alexander, N. A. Trout, K. D. King, and W. D. Lawrance, Chem. Phys. Lett., 1999, 299, 291.
R. Becerra, S. E. Boganov, M. P. Egorov, V. Ya. Lee, O. M. Nefedov, and R. Walsh, Chem. Phys. Lett., 1996, 250, 111.
R. Becerra, M. P. Egorov, I. V. Krylova, O. M. Nefedov, and R. Walsh, Chem. Phys. Lett., 2002, 351, 47.
J. E. Baggott, M. A. Blitz, H. M. Frey, P. D. Lightfoot, and R. Walsh, Chem. Phys. Lett., 1987, 135, 39.
E. C.-L. Ma, D. P. Paquin, and P. P. Gaspar, J. Chem. Soc., Chem. Comm., 1980, 381.
E. C.-L. Ma, K. Kobayashi, M. W. Barzilai, and P. P. Gaspar, J. Organomet. Chem., 1982, 224, C13.
D. Lei and P. P. Gaspar, Polyhedron, 1991, 10, 1221.
W. Du, L. A. Keeling, and C. M. Greenlief, J. Vac. Sci. Technol. A, 1994, 12, 2281.
C. Isobe, H. Cho, and J. E. Crowell, Surf. Sci., 1993, 295, 117.
H. Simka, M. Hierlemann, M. Utz, and K. F. Jensen, J. Electrochem. Soc., 1996, 143, 2646.
C. G. Newman, J. Dzarnoski, M. A. Ring, and H. E. O’Neal, Int. J. Chem. Kinet., 1980, 12, 661.
R. Becerra, S. E. Boganov, M. P. Egorov, V. I. Faustov, O. M. Nefedov, and R. Walsh, J. Am. Chem. Soc., 1998, 120, 12657.
K. Saito and K. Obi, Chem. Phys. Lett., 1993, 215, 193.
K. Obi, M. Fukushima, and K. Saito, Appl. Surf. Sci., 1994, 79/80, 465.
K. Saito and K. Obi, Chem. Phys., 1994, 187, 381.
J. Karolczak, W. P. Harper, R. S. Grev, and D. J. Clouthier, J. Chem. Phys., 1995, 103, 2839.
A. Campargue and R. Escribano, Chem. Phys. Lett., 1999, 315, 397.
W. J. Leigh, C. R. Harrington, and I. Vargas-Baca, J. Am. Chem. Soc., 2004, 126, 16105.
J. M. Jasinski, B. S. Meyerson, and B. A. Scott, Annu. Rev. Phys. Chem., 1987, 38, 109.
G. Lu and J. E. Crowell, J. Chem. Phys., 1993, 98, 3415.
P. P. Gaspar, C. A. Levy, J. J. Frost, and S. A. Bock, J. Am. Chem. Soc., 1969, 91, 1573.
P. Estacio, M. D. Sefcik, E. K. Chan, and M. A. Ring, Inorg. Chem., 1970, 9, 1068.
M. D. Sefcik and M. A. Ring, J. Organomet. Chem., 1973, 59, 167.
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.
J. E. Baggott, M. A. Blitz, H. M. Frey, and R. Walsh, J. Am. Chem. Soc., 1990, 112, 8337.
J. E. Baggott, H. M. Frey, P. D. Lightfoot, R. Walsh, and I. M. Watts, J. Chem. Soc., Faraday Trans., 1990, 86, 27.
R. Becerra, S. E. Boganov, M. P. Egorov, V. I. Faustov, O. M. Nefedov, and R. Walsh, Phys. Chem. Chem. Phys., 2001, 3, 184.
R. Becerra, S. E. Boganov, M. P. Egorov, O. M. Nefedov, and R. Walsh, Mendeleev Commun., 1997, 87.
R. Becerra and R. Walsh, Phys. Chem. Chem. Phys., 1999, 1, 5301.
U. N. Alexander, K. D. King, and W. D. Lawrance, Chem. Phys. Lett., 2000, 319, 529.
R. Becerra, H. M. Frey, B. P. Mason, R. Walsh, and M. S. Gordon, J. Chem. Soc., Faraday Trans., 1995, 91, 2723.
R. Becerra, S. Boganov, and R. Walsh, J. Chem. Soc., Faraday Trans., 1998, 94, 3569.
I. W. Carpenter, PhD Thesis, University of Reading, 1996.
J. Troe, J. Chem. Soc., Faraday Trans., 1994, 90, 2303.
G. Trinquier, J. Chem. Soc., Faraday Trans., 1993, 89, 775.
R. Becerra, H. M. Frey, B. P. Mason, and R. Walsh, J. Chem. Soc., Faraday Trans., 1993, 89, 411.
P. N. Noble and R. Walsh, Int. J. Chem. Kinet., 1983, 15, 547.
R. Becerra and R. Walsh, Int. J. Chem. Kinet., 1999, 31, 393.
R. Walsh, Pure Appl. Chem., 1987, 59, 69.
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.
J. E. Baggott, M. A. Blitz, H. M. Frey, P. D. Lightfoot, and R. Walsh, Int. J. Chem. Kinet., 1992, 24, 127.
U. N. Alexander, K. D. King, and W. D. Lawrance, Phys. Chem. Chem. Phys., 2001, 3, 3085.
M. W. Heaven, G. F. Metha, and M. A. Buntine, J. Phys. Chem., A, 2001, 105, 1185.
S. Su and M. S. Gordon, Chem. Phys. Lett., 1993, 204, 306.
R. Becerra, S. E. Boganov, M. P. Egorov, V. I. Faustov, O. M. Nefedov, and R. Walsh, Can. J. Chem., 2000, 78, 1428.
J. M. Jasinski, J. Phys. Chem., 1986, 90, 555.
M. S. Gordon, D. R. Gano, J. S. Binkley, and M. J. Frisch, J. Am. Chem. Soc., 1986, 108, 2191.
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.
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.
R. Becerra and R. Walsh, Phys. Chem. Chem. Phys., 2002, 4, 6001.
R. Becerra and R. Walsh, J. Organomet. Chem., 2001, 636, 49.
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.
N. Al-Rubaiey and R. Walsh, J. Phys. Chem., 1994, 98, 5303.
N. Al-Rubaiey, R. Becerra, and R. Walsh, Phys. Chem. Chem. Phys., 2002, 4, 5072.
N. Al-Rubaiey, I. W. Carpenter, R. Walsh, R. Becerra, and M. S. Gordon, J. Phys. Chem., A, 1998, 102, 8564.
R. Becerra, H. M. Frey, B. P. Mason, and R. Walsh, J. Chem. Soc., Chem. Commun., 1993, 1050.
R. Becerra and R. Walsh, Int. J. Chem. Kinet., 1994, 26, 45.
R. Becerra, J. P. Cannady, and R. Walsh, Phys. Chem. Chem. Phys., 2001, 3, 2343.
R. Becerra, J. P. Cannady, and R. Walsh, J. Chem. Phys A., 2002, 106, 11558.
P. Antoniotti, P Benzi, M. Castiglioni, and P. Volpe, Eur. J. Inorg. Chem. 1999, 323.
S. Sakai, Int. J. Quantum Chem., 1998, 70, 291.
M.-D. Su and S.-Y. Chu, J. Am. Chem. Soc., 1999, 121, 11478.
D. A. Horner, R. S. Grev, and H. F. Schaefer III, J. Am. Chem. Soc., 1992, 114, 2093.
W. Ando, H. Ohgaki, and Y. Kabe, Angew. Chem. Int. Ed. Engl., 1994, 33, 659.
H. Ohgaki, Y. Kabe, and W. Ando, Organometallics, 1995, 14, 2139.
P. N. Skancke, D. A. Hrovat, and W. T. Borden, J. Am. Chem. Soc., 1997, 119, 8012.
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.
V. N. Khabashesku, S. E. Boganov, K. N. Kudin, J. L. Margrave, J. Michl, and O. M. Nefedov, Russ. Chem. Bull., 1999, 48, 2003.
F. Anwari and M. S. Gordon, Isr. J. Chem., 1983, 23, 129.
A. D. Krebs and J. Berndt, Tetrahedron Lett., 1983, 24, 4083.
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.
M. T. Nguyen, D. Sengupta, and L. G. Vanquickenborne, Chem. Phys. Lett., 1995, 240, 513.
P. N. Skancke, D. A. Hrovat, and W. T. Borden, J. Phys. Chem. A, 1999, 103, 4043.
G. Maier, H. P. Reisenauer, and H. Egenolf, Eur. J. Org. Chem., 1998, 1313.
K. A. Holbrook, M. J. Pilling, and S. H. Robertson, Unimolecular Reactions, Wiley, Chichester, 2nd edn., 1996.
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.
U. N. Alexander, K. D. King, and W. D. Lawrance, Phys. Chem. Chem. Phys., 2003, 5, 1557.
U. N. Alexander, K. D. King, and W. D. Lawrance, J. Phys. Chem. A, 2002, 106, 973.
R. Becerra, J. P. Cannady, and R. Walsh, J. Phys. Chem. A, 2003, 107, 11049.
M. W. Heaven, G. F. Metha, and M. A. Buntine, Aust. J. Chem., 2001, 54, 185.
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.
S. R. Gunn and L. G. Green, J. Phys. Chem., 1961, 65, 779.
S. R. Gunn and J. H. Kindsvater, J. Phys. Chem., 1966, 70, 1750.
M. J. Almond, A. M. Doncaster, P. N. Noble, and R. Walsh, J. Am. Chem. Soc., 1982, 104, 4717.
P. N. Noble and R. Walsh, Int. J. Chem. Kinet., 1983, 15, 547.
B. Ruscic, M. Schwartz, and J. Berkowitz, J. Chem. Phys., 1990, 92, 1865.
W. E. Dasent, Nonexistent Compounds, Arnold, London, 1965, Chapt. 5, p. 77.
S. W. Benson, Thermochemical Kinetics, Wiley, New York, 2nd edn., 1976.
J. A. Boatz and M. S. Gordon, J. Phys. Chem., 1989, 93, 3025.
J. A. Boatz, M. S. Gordon, and L. R. Sita, J. Phys. Chem., 1990, 94, 5488.
A. M. Doncaster and R. Walsh, J. Phys. Chem., 1979, 83, 578.
L. H. Long and C. I. Pulford, J. Chem. Soc., Faraday Trans., 1986, 82, 567.
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.
L. R. Sita and R. D. Bickerstaff, Phosphorus, Sulfur Silicon Relat. Elem., 1989, 41, 31.
J. P. Cotton, P. J. Davidson, M. F. Lappert, J. Chem. Soc., Dalton Trans., 1976, 2275.
U. N. Alexander, Ph. D. Thesis, Flinders University of South Australia, 2000.
Author information
Authors and Affiliations
Additional information
__________
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 3, pp. 477–505, March, 2005.
Rights and permissions
About this article
Cite this article
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
Received:
Revised:
Issue Date:
DOI: https://doi.org/10.1007/s11172-005-0285-5