Ring opening of cyclopropylidene and internal rotation of allene

Journal of Physical Chemistry

Volumn 100, Issue 40, 1996, Pages 16147-16154

  Bettinger, Holger F ^a   Schreiner, Peter R ^a   Schleyer, Paul V R ^a   Schaefer III, Henry F ^b  

^a UNIVERSITY OF ERLANGEN NUREMBERG   (Germany)

^b UNIVERSITY OF GEORGIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CALCULATIONS; HYDROCARBONS; MATHEMATICAL MODELS; MOLECULAR DYNAMICS; PHYSICAL CHEMISTRY; QUANTUM MECHANICS;

AB INITIO CALCULATIONS; ALLENE; INTERNAL ROTATION; INTRINSIC REACTION COORDINATES; RING OPENING;

ORGANIC COMPOUNDS;

EID: 0030567908     PISSN: 00223654     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp961343f     Document Type: Article

References (104)

1. Chapman, O. L. Pure Appl. Chem. 1974, 40, 511.
2. (a) Landolt-Börnstein Structure Data of Free Polyatomic Molecules, Suppl. to Vol. II/7 and II/15; Kuchitsu, K., Ed.; Springer-Verlag: Berlin, 1992; p 227.
3. (b) Runge, W. In The Chemistry of the Ketenes, Allenes and Related Compounds I: Patai, S., Ed.; Wiley: New York, 1980; p 45.
4. (c) Herzberg, G. Mol. Spectra Mol. Struct. III; Van Nostrand Reinhold: New York, 1966; p 640.
5. (d) Maki, A. G.; Toth, R. A. J. Mol. Spectrosc. 1965, 17, 136.
6. (e) Hirota, E.; Matsumura, C. J. Chem. Phys. 1973, 59, 3038.
7. For reviews on the synthesis of allenes via carbene intermediates see: (a) Backes, J.; Brinker, U. H. Meth. Org. Chem. (Houben-Weyl) 1989, E19b, 391-510.
8. (b) Landor, P. D. In The Chemistry of the Allenes; Landor, S. R., Ed.; Academic Press: London, 1980; Vol. 1, Chapter 2.
9. (c) Hopf, H. In The Chemistry of the Ketenes, Allenes and Related Compounds II; Patai, S., Ed.; Wiley: New York, 1980; pp 781-862.
10. (d) Murray, M. Meth. Org. Chem. (Houben-Weyl) 1977, 5/2a, 967-1076.
11. (e) Taylor, D. R. Chem. Rev. 1967, 67, 317.
12. Stierman, T. J.; Johnson, R. P. J. Am. Chem. Soc. 1985, 107, 3971.
13. (a) Honjou, N.; Pacansky, J.; Yoshimine, M. J. Am. Chem. Soc. 1985, 107, 5332.
14. (b) Yoshimine, M.; Pacansky, J.; Honjou, N. J. Am. Chem. Soc. 1989, 111, 4198.
15. (a) Valtazanos, P.; Elbert, S. T.; Xantheas, S.; Ruedenberg, K. Theor. Chim. Acta 1991, 78, 287.
16. (b) Xantheas, S.; Valtazanos, P.; Ruedenberg, K. Theor. Chim. Acta, 1991, 78, 327.
17. (c) Xantheas, S.; Elbert, S. T.; Ruedenberg, K. Theor. Chim. Acta, 1991, 78, 365.
18. (d) Valtazanos, P.; Ruedenberg, K. Theor. Chim. Acta, 1991, 78, 397.
19. Cramer, C. J.; Worthington, S. E. J. Phys. Chem. 1995, 99, 1462.
20. (a) Jones, W. M.; Walbrick, J. M. J. Org. Chem. 1969, 34, 2217.
21. (b) Walbrick, J. M.; Wilson Jr., W. M.; Jones, W. M. J. Am. Chem. Soc. 1968, 90, 2895.
22. (c) Jones, W. M.; Wilson Jr., J. W. Tetrahedron Lett. 1965, 21, 1587.
23. (d) Jones, W. M., Wilson Jr., J. W.; Tutwiler, F. B. J. Am. Chem. Soc. 1963, 85, 3309.
24. Jones, W. M.; Krause, D. L. J. Am. Chem. Soc. 1971, 93, 551.
25. (a) Bodor, N.; Dewar, M. J. S.; Maksic, Z. B. J. Am. Chem. Soc. 1973, 95, 5245.
26. (b) Dewar, M. J. S.; Hasselbach, E.; Shanshal, M. J. Am. Chem. Soc. 1970, 92, 3505.
27. (a) Schleyer, P. v. R.; Van Dine, G. W.; Schöllkopf, U.; Paust, J. J. Am. Chem. Soc. 1966, 88, 2868.
28. (b) Schleyer, P. v. R.; Su, T. M.; Saunders, M.; Rosenfeld, J. C. J. Am. Chem. Soc. 1969, 91, 5174.
29. (c) Schleyer, P. v. R.; Sliwinski, W. F.; Van Dine, G. W.; Schöllkopf, U.; Paust, J.; Fellenberger, K. J. Am. Chem. Soc. 1972, 94, 125.
30. (d) Radom, L.; Hariharan, P. C.; Pople, J. A.; Schleyer, P. v. R. J. Am. Chem. Soc. 1973, 95, 6531.
31. Woodward, R. B.; Hoffmann, R. Angew. Chem., Int. Ed. Engl. 1969, 8, 781.
32. Pasto, D. J.; Haley, M.; Chipman, D. M. J. Am. Chem. Soc. 1978, 100, 5272.
33. Rauk, A.; Bouma, W. J.; Radom, L. J. Am. Chem. Soc. 1985, 107, 3780.
34. Valtazanos, P.; Ruedenberg, K. Theor. Chim. Acta 1986, 69, 281.
35. (a) Ruedenberg, K.; Sundberg, K. R. In Quantum Science; Calais, J.-L., Goscinski, O., Linderberg, J., Ohrn, Y., Eds.; Plenum: New York, 1976.
36. (b) Ruedenberg, K.; Schmidt, M. W.; Gilbert, M. M.; Elbert, S. T. Chem. Phys. 1982, 71, 41, 65.
37. (c) Ruedenberg, K.; Schmidt, M. W.; Gilbert, M. M. Chem. Phys. 1982, 71, 51.
38. For reviews of the CASSCF method see: (a) Werner, H.-J. Adv. Chem. Phys. 1987, 69, 1.
39. (b) Shepard, R. Adv. Chem. Phys. 1987, 69, 63.
40. (c) Roos, B. O. Adv. Chem. Phys. 1987, 69, 399.
41. (d) Siegbahn, P. E. M. Faraday Symp. Chem. Soc. 1984, 19, 97.
42. The two saddle points were obtained by numerical evaluation of a polynomial obtained from the theoretical PES.
43. Roth, W. R.; Ruf, G.; Ford, P. W. Chem. Ber. 1974, 107, 48.
44. Seeger, R.; Krishnan, R.; Pople, J. A.; Schleyer, P. v. R. J. Am. Chem. Soc. 1977, 99, 7103.
45. (a) Pulay, P.; Hamilton, T. P. J. Chem. Phys. 1988, 88, 4926.
46. (b) Bofill, J. M.; Pulay, P. J. Chem. Phys. 1989, 90, 3637.
47. (a) Hohenberg, P.; Kohn, W. Phys. Rev. B 1964, 136, 864.
48. (b) Kohn, W.; Sham, L. J. Phys. Rev. A 1965, 140, 1133.
49. (c) Parr, R. G.; Yang, W. Density Functional Theory of Atoms and Molecules; Oxford University Press: Oxford, U.K., 1989.
50. (c) Density Functional Methods in Chemistry; Labanowski, J. K., Andzelm, J. W., Eds.; Springer: Berlin, 1991.
51. (d) Modern Density Functional Theory: A Tool for Chemistry; Seminario, J. M., Politzer, P., Eds.; Elsevier: Amsterdam, 1995.
52. (a) Gill, P. M. W.; Johnson, B. G.; Pople, J. A.; Frisch, M. J. Chem. Phys. Lett. 1992, 197, 499.
53. (b) Johnson, B. G.; Gill, P. M. W.; Pople, J. A. J. Chem. Phys. 1993, 98, 5612.
54. (c) Handy, N. C.; Murray, C. W.; Amos, R. D. J. Phys. Chem. 1993, 97, 4392.
55. (d) Murray, C. W.; Handy, N. C.; Amos, R. D. J. Chem. Phys. 1993, 98, 7145.
56. (e) Dibble, T. S.; Francisco, J. S.; Deeth, R. J.; Hand, M. R.; Williams, I. H. J. Chem. Phys. 1994, 100, 459.
57. (f) Rauhut, G.; Pulay, P. J. Phys. Chem. 1995, 99, 3093.
58. (g) Ziegler, T. Can. J. Chem. 1995, 73, 743.
59. (h) Ziegler, T. Chem. Rev. 1991, 91, 651.
60. (i) Schreiner, P. R.; Karney, W. L.; Schleyer, P. v. R.; Borden, W. T.; Hamilton, T. P.; Schaefer, H. F. J. Org. Chem., in press.
61. (j) Xie, Y.; Schreiner, P. R.; Schaefer, H. F.; Schleyer, P. v. R. J. Am. Chem. Soc., submitted.
62. Hehre, W. J.; Radom, L.; Schleyer, P. v. R.; Pople, J. A. Ab initio Molecular Orbital Theory; Wiley: New York, 1986; Chapter 4.3.
63. Huzinaga, S. J. Chem. Phys. 1965, 42, 1293.
64. Dunning, T. H. J. Chem. Phys. 1971, 55, 716.
65. Becke, A. D. J. Chem. Phys. 1993, 98, 5648.
66. Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785.
67. Gaussian 92/DFT, Revision G.2; Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Gill, P. M. W.; Johnson, B. G.; Wong, M. W.; Foresman, J. B.; Robb, M. A.; Head-Gordon, M.; Replogle, E. S.; Gomperts, R.; Andres, J. L.; Raghavachari, K.; Binkley, J. S.; Gonzalez, C.; Martin, R. L.; Fox, D. J.; Defrees, D. J.; Baker, J.; Stewart, J. J. P.; Pople, J. A. Gaussian, Inc., Pittsburgh, PA, 1993.
68. (a) Brooks, B. R.; Laidig, W. D.; Saxe, P.; Goddard, J. D.; Yamaguchi, Y.; Schaefer, H. F. J. Chem. Phys. 1980, 72, 4652.
69. (b) Rice, J. E.; Amos, R. D.; Handy, N. C.; Lee, T. J.; Schaefer, H. F. J. Chem. Phys. 1982, 77, 5647.
70. Langhoff, S. R.; Davidson, E. R. Int. J. Quantum Chem. 1974, 8, 61.
71. Löwdin, P.-O. Phys. Rev. 1955, 97, 1474.
72. Schaefer, H. F. Quantum Chemistry, The Development of Ab Initio Methods in Molecular Electronic Structure Theory; Clarendon Press: Oxford, U.K., 1985.
73. Scuseria, G. E. Chem. Phys. Lett. 1991 176, 27.
74. Bunker, P. R.; Jensen, P.; Kraemer, W. P.; Beardsworth, R. J. Chem. Phys. 1986, 85, 3724.
75. (a) Fukui, K. J. Phys. Chem. 1970, 74, 4161.
76. (b) Schaefer, H. F. Chem. Brit. 1975, 11, 227.
77. (c) Fukui, K. Acc. Chem. Res. 1981, 14, 363.
78. (a) Gonzalez, C.; Schlegel, H. B. J. Chem. Phys. 1989, 90, 2154.
79. (b) Gonzalez, C.; Schlegel, H. B. J. Phys. Chem. 1990, 94, 5523.
80. PSI2.0.8; Janssen, C. L.; Seidl, E. T.; Scuseria, G. E.; Hamilton, T. P.; Yamaguchi, Y.; Remington, R. B.; Xie, Y.; Vacek, G.; Sherrill, C. D.; Crawford, T. D.; Fermann, J. T.; Allen, W. D.; Brooks, B. R.; Fitzgerald, G. B.; Fox, D. J.; Gaw, J. F.; Handy, N. C.; Laidig, W. D.; Lee, T. J.; Pitzer, R. M.; Rice, J. E.; Saxe, P.; Scheiner, A. C.; Schaefer, H. F. PSITECH, Inc.: Watkinsville, GA, 30677, 1994.
81. Lee, T. J.; Rice, J. E.; Scuseria, G. E.; Schaefer, H. F. Theor. Chim. Acta 1989, 75, 81.
82. (b) Lee, T. J.; Taylor, P. R. Int. J. Quantum Chem. Symp. 1989, 23, 199.
83. (c) Lee, T. J.; Rendell, A. P.; Taylor, P. R. J. Phys. Chem. 1990, 94, 5463.
84. Richards, C. A.; Kim, S.-J.; Yamaguchi, Y.; Schaefer, H. F. J. Am. Chem. Soc. 1995, 117, 10104.
85. (a) Walsh, A. D. J. Chem. Soc. 1953, 2260.
86. (b) Walsh, A. D. J. Chem. Soc. 1953, 2266.
87. (c) Mulliken, R. S. J. Am. Chem. Soc. 1955, 77, 887.
88. Kozlowski, P. M.; Rauhut, G.; Pulay, P. J. Chem. Phys. 1995, 103, 5650.
89. (a) Borden, W. T.; Davidson, E. R. Acc. Chem. Res. 1996, 29, 67.
90. (b) Kozlowski, P. M.; Dupuis, M.; Davidson, E. R. J. Am. Chem. Soc. 1995, 117, 774.
91. (c) Jiao, H.; Schleyer, P. v. R. Angew. Chem., Int. Ed. Engl. 1995, 34, 334.
92. Pople, J. A.; Gill, P. M. W.; Johnson, B. G. Chem. Phys. Lett. 1992, 199, 557.
93. Baker, J.; Scheiner, A.; Andzelm, J. Chem. Phys. Lett. 1993, 216, 380.
94. Szabo, A.; Ostlund, N. S. Modern Quantum Chemistry; Macmillan: New York, 1982.
95. (a) Keith, T. A.; Frisch, M. J., manuscript in preparation.
96. (b) Seeger, R.; Pople, J. A. J. Chem. Phys 1977, 66, 3045.
97. (c) Ostlund, N. S. J. Chem. Phys. 1972, 57, 2994.
98. Dykstra, C. E.; Schaefer, H. F. In The Chemistry of the Ketenes, Allenes and Related Compounds I; Patai, S., Ed.; Wiley: New York, 1980; p 11.
99. (a) Buenker, R. J. J. Chem. Phys. 1968, 48, 1368.
100. (b) Schaad, L. J.; Burnelle, L. A.; Dressier, K. P. Theor. Chim. Acta 1969, 15, 91.
101. (c) Radom, L.; Pople, J. A. J. Am. Chem. Soc. 1970, 92, 4786.
102. Bingham, R. C.; Dewar, M. J. S.; Lo, D. H. J. Am. Chem. Soc. 1975, 97, 1294.
103. (e) Staemmler, V. Theor. Chim. Acta 1977, 45, 89.
104. (f) Dykstra, C. E. J. Am. Chem. Soc. 1977, 99, 2060.