[2+2] Cycloaddition reactions of ethylene derivatives with the Si(100)-2 × 1 surface: A theoretical study

Journal of Physical Chemistry B

Volumn 109, Issue 11, 2005, Pages 5199-5206

  Wang, Yong ^a   Ma, Jing ^a   Inagaki, Satoshi ^b   Pei, Yong ^b  

^a NANJING UNIVERSITY   (China)

^b GIFU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ACTIVATION ENERGY; DIMERS; ETHYLENE; MICROELECTRONICS; REACTION KINETICS; SCANNING TUNNELING MICROSCOPY; THERMOANALYSIS; UNSATURATED COMPOUNDS;

CYCLOADDITION REACTIONS; DENSITY FUNCTIONAL THEORY (DFT); NATURAL BOND ORBITAL (NBO); UNSATURATED MOLECULES;

DERIVATIVES;

EID: 15744363460     PISSN: 15206106     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp0450080     Document Type: Article

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24. For examples of cycloaddition reaction of ethylene with the Si-(100)-2 × 1 surface, see: (a) Yoshinobu, J.; Tsuda, H.; Onchi, M.; Nishijima, M. J. J. Chem. Phys. 1987, 87, 7332. (b) Clemen, L.; Wallace, R. M.; Taylor, P. A.; Choyke, W. J.; Weinberg, W. H.; Yates, J. T. Surf. Sci. 1992, 268, 205. (c) Kusunoki, I.; takagaki. T.; Ishidzuka, S.; Igari, Y.; Takaoka, T. Surf. Sci. 1997, 380, 131. (d) Ikeda, M.; Maruoka, T.; Nagashima, N. Surf. Sci. 1998, 416, 240. (e) Miotto, R.; Ferraz, A. C.; Srivastava, G. P. Surf. Sci. 2002, 507-570, 12. (f) Yamashita, Y.; Machida, S.; Nagao, M.; Yamamoto, S.; Mukai, K.; Yoshinobu, J. Chem. Phys. Lett. 2003, 374, 476. (g) Masashi, N.; Hirobumi, U.; Kozo, M.; Yoshiyuki, Y.; Jun, Y.; Kazuto, A.; Shinji, T. J. Am. Chem. Soc. 2004, 126, 9922. (h) Cho, J.-H.; Kleinman, L. Phys. Rev. B 2004, 69, 075303 and references therein.
25. For examples of cycloaddition reaction of ethylene with the Si-(100)-2 × 1 surface, see: (a) Yoshinobu, J.; Tsuda, H.; Onchi, M.; Nishijima, M. J. J. Chem. Phys. 1987, 87, 7332. (b) Clemen, L.; Wallace, R. M.; Taylor, P. A.; Choyke, W. J.; Weinberg, W. H.; Yates, J. T. Surf. Sci. 1992, 268, 205. (c) Kusunoki, I.; takagaki. T.; Ishidzuka, S.; Igari, Y.; Takaoka, T. Surf. Sci. 1997, 380, 131. (d) Ikeda, M.; Maruoka, T.; Nagashima, N. Surf. Sci. 1998, 416, 240. (e) Miotto, R.; Ferraz, A. C.; Srivastava, G. P. Surf. Sci. 2002, 507-570, 12. (f) Yamashita, Y.; Machida, S.; Nagao, M.; Yamamoto, S.; Mukai, K.; Yoshinobu, J. Chem. Phys. Lett. 2003, 374, 476. (g) Masashi, N.; Hirobumi, U.; Kozo, M.; Yoshiyuki, Y.; Jun, Y.; Kazuto, A.; Shinji, T. J. Am. Chem. Soc. 2004, 126, 9922. (h) Cho, J.-H.; Kleinman, L. Phys. Rev. B 2004, 69, 075303 and references therein.
26. For examples of cycloaddition reaction of ethylene with the Si-(100)-2 × 1 surface, see: (a) Yoshinobu, J.; Tsuda, H.; Onchi, M.; Nishijima, M. J. J. Chem. Phys. 1987, 87, 7332. (b) Clemen, L.; Wallace, R. M.; Taylor, P. A.; Choyke, W. J.; Weinberg, W. H.; Yates, J. T. Surf. Sci. 1992, 268, 205. (c) Kusunoki, I.; takagaki. T.; Ishidzuka, S.; Igari, Y.; Takaoka, T. Surf. Sci. 1997, 380, 131. (d) Ikeda, M.; Maruoka, T.; Nagashima, N. Surf. Sci. 1998, 416, 240. (e) Miotto, R.; Ferraz, A. C.; Srivastava, G. P. Surf. Sci. 2002, 507-510, 12. (f) Yamashita, Y.; Machida, S.; Nagao, M.; Yamamoto, S.; Mukai, K.; Yoshinobu, J. Chem. Phys. Lett. 2003, 374, 476. (g) Masashi, N.; Hirobumi, U.; Kozo, M.; Yoshiyuki, Y.; Jun, Y.; Kazuto, A.; Shinji, T. J. Am. Chem. Soc. 2004, 126, 9922. (h) Cho, J.-H.; Kleinman, L. Phys. Rev. B 2004, 69, 075303 and references therein.
27. For examples of cycloaddition reaction of ethylene with the Si-(100)-2 × 1 surface, see: (a) Yoshinobu, J.; Tsuda, H.; Onchi, M.; Nishijima, M. J. J. Chem. Phys. 1987, 87, 7332. (b) Clemen, L.; Wallace, R. M.; Taylor, P. A.; Choyke, W. J.; Weinberg, W. H.; Yates, J. T. Surf. Sci. 1992, 268, 205. (c) Kusunoki, I.; takagaki. T.; Ishidzuka, S.; Igari, Y.; Takaoka, T. Surf. Sci. 1997, 380, 131. (d) Ikeda, M.; Maruoka, T.; Nagashima, N. Surf. Sci. 1998, 416, 240. (e) Miotto, R.; Ferraz, A. C.; Srivastava, G. P. Surf. Sci. 2002, 507-570, 12. (f) Yamashita, Y.; Machida, S.; Nagao, M.; Yamamoto, S.; Mukai, K.; Yoshinobu, J. Chem. Phys. Lett. 2003, 374, 476. (g) Masashi, N.; Hirobumi, U.; Kozo, M.; Yoshiyuki, Y.; Jun, Y.; Kazuto, A.; Shinji, T. J. Am. Chem. Soc. 2004, 126, 9922. (h) Cho, J.-H.; Kleinman, L. Phys. Rev. B 2004, 69, 075303 and references therein.
28. For examples of cycloaddition reaction of ethylene with the Si-(100)-2 × 1 surface, see: (a) Yoshinobu, J.; Tsuda, H.; Onchi, M.; Nishijima, M. J. J. Chem. Phys. 1987, 87, 7332. (b) Clemen, L.; Wallace, R. M.; Taylor, P. A.; Choyke, W. J.; Weinberg, W. H.; Yates, J. T. Surf. Sci. 1992, 268, 205. (c) Kusunoki, I.; takagaki. T.; Ishidzuka, S.; Igari, Y.; Takaoka, T. Surf. Sci. 1997, 380, 131. (d) Ikeda, M.; Maruoka, T.; Nagashima, N. Surf. Sci. 1998, 416, 240. (e) Miotto, R.; Ferraz, A. C.; Srivastava, G. P. Surf. Sci. 2002, 507-570, 12. (f) Yamashita, Y.; Machida, S.; Nagao, M.; Yamamoto, S.; Mukai, K.; Yoshinobu, J. Chem. Phys. Lett. 2003, 374, 476. (g) Masashi, N.; Hirobumi, U.; Kozo, M.; Yoshiyuki, Y.; Jun, Y.; Kazuto, A.; Shinji, T. J. Am. Chem. Soc. 2004, 126, 9922. (h) Cho, J.-H.; Kleinman, L. Phys. Rev. B 2004, 69, 075303 and references therein.
29. For examples of cycloaddition reaction of ethylene with the Si-(100)-2 × 1 surface, see: (a) Yoshinobu, J.; Tsuda, H.; Onchi, M.; Nishijima, M. J. J. Chem. Phys. 1987, 87, 7332. (b) Clemen, L.; Wallace, R. M.; Taylor, P. A.; Choyke, W. J.; Weinberg, W. H.; Yates, J. T. Surf. Sci. 1992, 268, 205. (c) Kusunoki, I.; takagaki. T.; Ishidzuka, S.; Igari, Y.; Takaoka, T. Surf. Sci. 1997, 380, 131. (d) Ikeda, M.; Maruoka, T.; Nagashima, N. Surf. Sci. 1998, 416, 240. (e) Miotto, R.; Ferraz, A. C.; Srivastava, G. P. Surf. Sci. 2002, 507-570, 12. (f) Yamashita, Y.; Machida, S.; Nagao, M.; Yamamoto, S.; Mukai, K.; Yoshinobu, J. Chem. Phys. Lett. 2003, 374, 476. (g) Masashi, N.; Hirobumi, U.; Kozo, M.; Yoshiyuki, Y.; Jun, Y.; Kazuto, A.; Shinji, T. J. Am. Chem. Soc. 2004, 126, 9922. (h) Cho, J.-H.; Kleinman, L. Phys. Rev. B 2004, 69, 075303 and references therein.
30. For examples of cycloaddition reaction of acetylene with the Si-(100)-2 × 1 surface, see: (a) Taylor, P. A.; Wallace, R. M.; Cheng, C. C.; Weinberg, W. H.; Dresser, M. J.; Choyke, W. J.; T., Y. J. J. Am. Chem. Soc. 1992, 114, 6754. (b) Li, L.; Tindall, C.; Takaoka, O.; Hasegawa, Y.; Saknrai, T. Phys. Rev. B 1997, 56, 4648. (c) Fisher, A. J.; Blöchl, P. E.; Briggs, G. A. D. Surf. Sci. 1997, 374, 298 and references therein. (d) Dyson, A. J.; Smith, P. V. Surf. Sci. 1997, 375, 45. (e) Hofer, W. A.; Fisher, A. J.; Wolkow, R. A. Surf. Sci. 2001, 475, 83. (f) Wondong, K.; Hanchul, K.; Geunseop, L.; Jaegwan, C.; You, S.-Y.; Hong, Y.-K.; Koo, J.-Y. Surf. Sci. 2002, 514, 376 and references therein. (g) Jamie, M. R.; Gordon, M. S. J. Phys. Chem. B 2004, 108, 7820 and references therein; also see ref 18g.
31. For examples of cycloaddition reaction of acetylene with the Si-(100)-2 × 1 surface, see: (a) Taylor, P. A.; Wallace, R. M.; Cheng, C. C.; Weinberg, W. H.; Dresser, M. J.; Choyke, W. J.; T., Y. J. J. Am. Chem. Soc. 1992, 114, 6754. (b) Li, L.; Tindall, C.; Takaoka, O.; Hasegawa, Y.; Saknrai, T. Phys. Rev. B 1997, 56, 4648. (c) Fisher, A. J.; Blöchl, P. E.; Briggs, G. A. D. Surf. Sci. 1997, 374, 298 and references therein. (d) Dyson, A. J.; Smith, P. V. Surf. Sci. 1997, 375, 45. (e) Hofer, W. A.; Fisher, A. J.; Wolkow, R. A. Surf. Sci. 2001, 475, 83. (f) Wondong, K.; Hanchul, K.; Geunseop, L.; Jaegwan, C.; You, S.-Y.; Hong, Y.-K.; Koo, J.-Y. Surf. Sci. 2002, 514, 376 and references therein. (g) Jamie, M. R.; Gordon, M. S. J. Phys. Chem. B 2004, 108, 7820 and references therein; also see ref 18g.
32. For examples of cycloaddition reaction of acetylene with the Si-(100)-2 × 1 surface, see: (a) Taylor, P. A.; Wallace, R. M.; Cheng, C. C.; Weinberg, W. H.; Dresser, M. J.; Choyke, W. J.; T., Y. J. J. Am. Chem. Soc. 1992, 114, 6754. (b) Li, L.; Tindall, C.; Takaoka, O.; Hasegawa, Y.; Saknrai, T. Phys. Rev. B 1997, 56, 4648. (c) Fisher, A. J.; Blöchl, P. E.; Briggs, G. A. D. Surf. Sci. 1997, 374, 298 and references therein. (d) Dyson, A. J.; Smith, P. V. Surf. Sci. 1997, 375, 45. (e) Hofer, W. A.; Fisher, A. J.; Wolkow, R. A. Surf. Sci. 2001, 475, 83. (f) Wondong, K.; Hanchul, K.; Geunseop, L.; Jaegwan, C.; You, S.-Y.; Hong, Y.-K.; Koo, J.-Y. Surf. Sci. 2002, 514, 376 and references therein. (g) Jamie, M. R.; Gordon, M. S. J. Phys. Chem. B 2004, 108, 7820 and references therein; also see ref 18g.
33. For examples of cycloaddition reaction of acetylene with the Si-(100)-2 × 1 surface, see: (a) Taylor, P. A.; Wallace, R. M.; Cheng, C. C.; Weinberg, W. H.; Dresser, M. J.; Choyke, W. J.; T., Y. J. J. Am. Chem. Soc. 1992, 114, 6754. (b) Li, L.; Tindall, C.; Takaoka, O.; Hasegawa, Y.; Saknrai, T. Phys. Rev. B 1997, 56, 4648. (c) Fisher, A. J.; Blöchl, P. E.; Briggs, G. A. D. Surf. Sci. 1997, 374, 298 and references therein. (d) Dyson, A. J.; Smith, P. V. Surf. Sci. 1997, 375, 45. (e) Hofer, W. A.; Fisher, A. J.; Wolkow, R. A. Surf. Sci. 2001, 475, 83. (f) Wondong, K.; Hanchul, K.; Geunseop, L.; Jaegwan, C.; You, S.-Y.; Hong, Y.-K.; Koo, J.-Y. Surf. Sci. 2002, 514, 376 and references therein. (g) Jamie, M. R.; Gordon, M. S. J. Phys. Chem. B 2004, 108, 7820 and references therein; also see ref 18g.
34. For examples of cycloaddition reaction of acetylene with the Si-(100)-2 × 1 surface, see: (a) Taylor, P. A.; Wallace, R. M.; Cheng, C. C.; Weinberg, W. H.; Dresser, M. J.; Choyke, W. J.; T., Y. J. J. Am. Chem. Soc. 1992, 114, 6754. (b) Li, L.; Tindall, C.; Takaoka, O.; Hasegawa, Y.; Saknrai, T. Phys. Rev. B 1997, 56, 4648. (c) Fisher, A. J.; Blöchl, P. E.; Briggs, G. A. D. Surf. Sci. 1997, 374, 298 and references therein. (d) Dyson, A. J.; Smith, P. V. Surf. Sci. 1997, 375, 45. (e) Hofer, W. A.; Fisher, A. J.; Wolkow, R. A. Surf. Sci. 2001, 475, 83. (f) Wondong, K.; Hanchul, K.; Geunseop, L.; Jaegwan, C.; You, S.-Y.; Hong, Y.-K.; Koo, J.-Y. Surf. Sci. 2002, 514, 376 and references therein. (g) Jamie, M. R.; Gordon, M. S. J. Phys. Chem. B 2004, 108, 7820 and references therein; also see ref 18g.
35. For examples of cycloaddition reaction of acetylene with the Si-(100)-2 × 1 surface, see: (a) Taylor, P. A.; Wallace, R. M.; Cheng, C. C.; Weinberg, W. H.; Dresser, M. J.; Choyke, W. J.; T., Y. J. J. Am. Chem. Soc. 1992, 114, 6754. (b) Li, L.; Tindall, C.; Takaoka, O.; Hasegawa, Y.; Saknrai, T. Phys. Rev. B 1997, 56, 4648. (c) Fisher, A. J.; Blöchl, P. E.; Briggs, G. A. D. Surf. Sci. 1997, 374, 298 and references therein. (d) Dyson, A. J.; Smith, P. V. Surf. Sci. 1997, 375, 45. (e) Hofer, W. A.; Fisher, A. J.; Wolkow, R. A. Surf. Sci. 2001, 475, 83. (f) Wondong, K.; Hanchul, K.; Geunseop, L.; Jaegwan, C.; You, S.-Y.; Hong, Y.-K.; Koo, J.-Y. Surf. Sci. 2002, 514, 376 and references therein. (g) Jamie, M. R.; Gordon, M. S. J. Phys. Chem. B 2004, 108, 7820 and references therein; also see ref 18g.
36. For examples of cycloaddition reaction of acetylene with the Si-(100)-2 × 1 surface, see: (a) Taylor, P. A.; Wallace, R. M.; Cheng, C. C.; Weinberg, W. H.; Dresser, M. J.; Choyke, W. J.; T., Y. J. J. Am. Chem. Soc. 1992, 114, 6754. (b) Li, L.; Tindall, C.; Takaoka, O.; Hasegawa, Y.; Saknrai, T. Phys. Rev. B 1997, 56, 4648. (c) Fisher, A. J.; Blöchl, P. E.; Briggs, G. A. D. Surf. Sci. 1997, 374, 298 and references therein. (d) Dyson, A. J.; Smith, P. V. Surf. Sci. 1997, 375, 45. (e) Hofer, W. A.; Fisher, A. J.; Wolkow, R. A. Surf. Sci. 2001, 475, 83. (f) Wondong, K.; Hanchul, K.; Geunseop, L.; Jaegwan, C.; You, S.-Y.; Hong, Y.-K.; Koo, J.-Y. Surf. Sci. 2002, 514, 376 and references therein. (g) Jamie, M. R.; Gordon, M. S. J. Phys. Chem. B 2004, 108, 7820 and references therein; also see ref 18g.
37. For examples of cycloaddition reaction of benzene with the Si-(100)-2 × 1 surface, see: (a) Taguchi, Y.; Fujisawa, M.; Takaoka, T.; Okada, T.; Nishijima, M. J. Chem. Phys. 1991, 95, 6870. (b) Jeong, H. D.; Ryu, S.; Lee, Y. S.; Kim, S. Surf. Sci 1995, 344, L1226. (c) Kong, M. J.; Teplyakov, A. V.; Lyubovitsky, J. G.; Bent, S. F. Surf. Sci. 1998, 411, 286. (d) Lopinski, G. P.; Moffatt, D. J.; Wolkow, R. A. Chem. Phys. Lett. 1998, 282, 305. (e) Fink, A.; Menzel, D.; Widdra, W. J. Phys. Chem. B 2001, 105, 3828 and references therein. (f) Naumkin, F. Y.; Polanyi, J. C.; Rogers, D. Surf. Sci. 2003, 547, 335.
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