The naphthylcarbene potential energy hypersurface

Journal of the American Chemical Society

Volumn 119, Issue 6, 1997, Pages 1370-1377

  Xie, Yaoming ^a   Schreiner, Peter R ^a,b,c   Von Ragué Schleyer, Paul ^a,b   Schaefer III, Henry F ^a  

^a UNIVERSITY OF GEORGIA   (United States)

^b UNIVERSITY OF ERLANGEN NUREMBERG   (Germany)

^c UNIVERSITY OF GÖTTINGEN   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

POLYCYCLIC AROMATIC HYDROCARBON;

ARTICLE; DRUG STRUCTURE; MOLECULAR DYNAMICS; THEORY; THERMODYNAMICS;

EID: 0030978160     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9517072     Document Type: Article

References (69)

1. This topic has been reviewed extensively; see inter alia: (a) Wentrup, C. Top. Curr. Chem. 1976, 62, 173. (b) Jones, W. M. Acc. Chem. Res. 1977, 10, 353. (c) Jones, W. M.; Banker, U. H. In Pericyclic Reactions; Marchand, A. P., Lehr, A. E., Eds.; Academic Press: New York, 1977; Vol. 1, Chapter 3, p 149. (d) Wentrup, C. In Reactive Intermediates; Ambramovich, R., Ed.; Plenum Press: New York, 1980; Vol. 1, Chapter 4, p 263. (e) Wentrup, C. Reactive Molecules; Wiley-Interscience: New York, 1984; pp 220 and 242. (f) Moss, R. A.; Jones, M., Jr. Reactive Intermediates; Wiley: New York, 1985; Vol. 3, p 91.
2. This topic has been reviewed extensively; see inter alia: (a) Wentrup, C. Top. Curr. Chem. 1976, 62, 173. (b) Jones, W. M. Acc. Chem. Res. 1977, 10, 353. (c) Jones, W. M.; Banker, U. H. In Pericyclic Reactions; Marchand, A. P., Lehr, A. E., Eds.; Academic Press: New York, 1977; Vol. 1, Chapter 3, p 149. (d) Wentrup, C. In Reactive Intermediates; Ambramovich, R., Ed.; Plenum Press: New York, 1980; Vol. 1, Chapter 4, p 263. (e) Wentrup, C. Reactive Molecules; Wiley-Interscience: New York, 1984; pp 220 and 242. (f) Moss, R. A.; Jones, M., Jr. Reactive Intermediates; Wiley: New York, 1985; Vol. 3, p 91.
3. This topic has been reviewed extensively; see inter alia: (a) Wentrup, C. Top. Curr. Chem. 1976, 62, 173. (b) Jones, W. M. Acc. Chem. Res. 1977, 10, 353. (c) Jones, W. M.; Banker, U. H. In Pericyclic Reactions; Marchand, A. P., Lehr, A. E., Eds.; Academic Press: New York, 1977; Vol. 1, Chapter 3, p 149. (d) Wentrup, C. In Reactive Intermediates; Ambramovich, R., Ed.; Plenum Press: New York, 1980; Vol. 1, Chapter 4, p 263. (e) Wentrup, C. Reactive Molecules; Wiley-Interscience: New York, 1984; pp 220 and 242. (f) Moss, R. A.; Jones, M., Jr. Reactive Intermediates; Wiley: New York, 1985; Vol. 3, p 91.
4. This topic has been reviewed extensively; see inter alia: (a) Wentrup, C. Top. Curr. Chem. 1976, 62, 173. (b) Jones, W. M. Acc. Chem. Res. 1977, 10, 353. (c) Jones, W. M.; Banker, U. H. In Pericyclic Reactions; Marchand, A. P., Lehr, A. E., Eds.; Academic Press: New York, 1977; Vol. 1, Chapter 3, p 149. (d) Wentrup, C. In Reactive Intermediates; Ambramovich, R., Ed.; Plenum Press: New York, 1980; Vol. 1, Chapter 4, p 263. (e) Wentrup, C. Reactive Molecules; Wiley-Interscience: New York, 1984; pp 220 and 242. (f) Moss, R. A.; Jones, M., Jr. Reactive Intermediates; Wiley: New York, 1985; Vol. 3, p 91.
5. This topic has been reviewed extensively; see inter alia: (a) Wentrup, C. Top. Curr. Chem. 1976, 62, 173. (b) Jones, W. M. Acc. Chem. Res. 1977, 10, 353. (c) Jones, W. M.; Banker, U. H. In Pericyclic Reactions; Marchand, A. P., Lehr, A. E., Eds.; Academic Press: New York, 1977; Vol. 1, Chapter 3, p 149. (d) Wentrup, C. In Reactive Intermediates; Ambramovich, R., Ed.; Plenum Press: New York, 1980; Vol. 1, Chapter 4, p 263. (e) Wentrup, C. Reactive Molecules; Wiley-Interscience: New York, 1984; pp 220 and 242. (f) Moss, R. A.; Jones, M., Jr. Reactive Intermediates; Wiley: New York, 1985; Vol. 3, p 91.
6. This topic has been reviewed extensively; see inter alia: (a) Wentrup, C. Top. Curr. Chem. 1976, 62, 173. (b) Jones, W. M. Acc. Chem. Res. 1977, 10, 353. (c) Jones, W. M.; Banker, U. H. In Pericyclic Reactions; Marchand, A. P., Lehr, A. E., Eds.; Academic Press: New York, 1977; Vol. 1, Chapter 3, p 149. (d) Wentrup, C. In Reactive Intermediates; Ambramovich, R., Ed.; Plenum Press: New York, 1980; Vol. 1, Chapter 4, p 263. (e) Wentrup, C. Reactive Molecules; Wiley-Interscience: New York, 1984; pp 220 and 242. (f) Moss, R. A.; Jones, M., Jr. Reactive Intermediates; Wiley: New York, 1985; Vol. 3, p 91.
7. (a) Van der Stouw, G. G.; Shechter, H. Diss. Abstr. 1965, 25, 6974. Van der Stouw, G. G.; Kraska, A. R.; Shechter, H. J. Am. Chem. Soc. 1972, 94, 1655.
8. (a) Van der Stouw, G. G.; Shechter, H. Diss. Abstr. 1965, 25, 6974. Van der Stouw, G. G.; Kraska, A. R.; Shechter, H. J. Am. Chem. Soc. 1972, 94, 1655.
9. (b) Joines, R. C.; Turner, A. B.; Jones, W. M. J. Am. Chem. Soc. 1969, 91, 7754.
10. (c) Baron, W. J.; Jones, M., Jr.; Caspar, P. P. J. Am. Chem. Soc. 1970, 92, 4739.
11. (d) Wentrup, C.; Wilcek, K. Helv. Chim. Acta 1969, 53, 1459. Mayor, C.; Wentrup, C. J. Am. Chem. Soc. 1975, 97, 7467.
12. (d) Wentrup, C.; Wilcek, K. Helv. Chim. Acta 1969, 53, 1459. Mayor, C.; Wentrup, C. J. Am. Chem. Soc. 1975, 97, 7467.
13. (a) Matzinger, S.; Bally, T.; Patterson, E.; McMahon, R. J. J. Am. Chem. Soc. 1996, 118, 1535.
14. (b) Radom, L.; Schaefer, H. F.; Vincent, M. E. Nouv. J. Chim. 1980, 4, 411.
15. (c) Wong, M.-W.; Wentrup, C. J. Org. Chem. 1996, 61, 7022.
16. (d) Schreiner, P. R.; Karney, W. L.; Schleyer, P. v. R.; Borden, W. T.; Hamilton, T. P.; Schaefer, H. F. J. Org. Chem. 1996, 61, 7030.
17. Chapman, O. L.; Johnson, J. W.; McMahon, R. J.; West, P. R. J. Am. Chem. Soc. 1988, 110, 501.
18. Gaspar, P. P.; Hsu, J. P.; Chari, S. Tetrahedron 1985, 41, 1479.
19. Albrecht, S. W.; McMahon, R. J. J. Am. Chem. Soc. 1993, 115, 835.
20. (a) Janssen, C. L.; Schaefer, H. F. J. Am. Chem. Soc. 1987, 109, 5030.
21. (b) Jones, W. M.; Ennis, C. L. J. Am. Chem. Soc. 1969, 91, 6391.
22. (c) West, P. R.; Chapman, O. L.; LeRoux, J.-P. J. Am. Chem. Soc. 1982, 104, 1779.
23. (d) McMahon, R. J.; Chapman, O. L. J. Am. Chem. Soc. 1986, 108, 1713.
24. (e) Kuzaj, M.; Lüerssen, H.; Wentrup, C. Angew. Chem., Int. Ed. Engl. 1986, 25, 480.
25. Engler, T. A.; Shechter, H. Tetrahedron Lett. 1982, 23, 2715.
26. For a review see: Platz, M. S. In Kinetics and Spectroscopy of Carbenes and Biradicals; Platz, M. S., Ed.; Plenum Press: New York, 1990; Chapter 6.
27. (a) West, P. R.; Mooring, A. M.; McMahon, R. J.; Chapman, U. L. J. Org. Chem. 1986, 51, 1316.
28. (b) Chapman, O. L.; Sheridan, R. S.; LeRoux, J.-P. Recl. Trav. Chim. Pays-Bas 1979, 98, 334.
29. Barcus, R. L.; Hadel, L. M.; Johnston, L. J.; Platz, M. S.; Savino, T. G.; Scaiano, J. C. J. Am. Chem. Soc. 1986, 108, 3928.
30. Horn, K. A.; Chateauneuf, J. E. Tetrahedron 1985, 41, 1465.
31. Trozzolo, A. M.; Wasserman, E.; Yager, W. A. J. Am. Chem. Soc. 1965, 87, 129.
32. Senthilnathan, V. P.; Platz, M. S. J. Am. Chem. Soc. 1981, 103, 5503.
33. Coburn, T. T.; Jones, W. M. J. Am. Chem. Soc. 1974, 96, 5218.
34. Billups, W. E.; Lin, L. P.; Chow, W. Y. J. Am. Chem. Soc. 1974, 96, 4026.
35. Billups, W. E.; Haley, M. M.; Lee, G. A. Chem. Rev. 1989, 89, 1147.
36. Chateauneuf, J. E.; Horn, K. A.; Savino, T. G. J. Am. Chem. Soc. 1988, 110, 539.
37. Jones, W. M. In Rearrangements in Ground and Excited States; DeMayo, P., Ed.; Academic Press: New York, 1980; Vol. 1, Chapter 3.
38. Becker, J.; Wentrup, C. J. Chem. Soc., Chem. Commun. 1980, 190.
39. We used the program package VAMP 5.0: Rauhut, G.; Alex, A.; Chandrasekhar, J.; Steinke, T.; Clark, T.; Erlangen 1993.
40. Becke, A. D. Phys. Rev. A 1988, 38, 3098.
41. Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B, 1988, 37, 785.
42. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Gill, P. M. W.; Johnson, B. G.; Robb, M. A.; Cheeseman, J. R.; Keith, T.; Peterson, G. A.; Montgomery, J. A.; Raghavachari, K.; Al-Laham, M. A.; Zakrzewski, V. G.; Ortiz, J. V.; Foresman, J. B.; Cioslowski, J.; Stefanov, B. B.; Nanayakkara, A.; Challacombe, M.; Peng, C. Y.; Ayala, P. Y.; Chen, W.; Wong, M. W.; Andres, J. L.; Replogle, E. S.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Binkley, J. S.; Defrees, D. J.; Baker, J.; Stewart, J. P.; Head-Gordon, M.; Gonzalez, C.; Pople, J. A. GAUSSIAN94; Gaussian Inc.: Pittsburgh, PA, 1995.
43. Pople, J. A.; Krishnan, R.; Schlegel, H. B.; Binkley, J. S. Int. J. Quantum Chem. Symp. 1979, S13, 225.
44. Møller, C.; Plesset, M. S. Phys. Rev. 1934, 46, 618. Binkley, J. S.; Pople, J. A. Int. J. Quantum Chem. 1975, 9, 229. Pople, J. A.; Binkley, J. S.; Seeger, R. Int. J. Quantum Chem. 1976, S10, 1.
45. Møller, C.; Plesset, M. S. Phys. Rev. 1934, 46, 618. Binkley, J. S.; Pople, J. A. Int. J. Quantum Chem. 1975, 9, 229. Pople, J. A.; Binkley, J. S.; Seeger, R. Int. J. Quantum Chem. 1976, S10, 1.
46. Møller, C.; Plesset, M. S. Phys. Rev. 1934, 46, 618. Binkley, J. S.; Pople, J. A. Int. J. Quantum Chem. 1975, 9, 229. Pople, J. A.; Binkley, J. S.; Seeger, R. Int. J. Quantum Chem. 1976, S10, 1.
47. Hehre, W. J.; Radom, L.; Pople, J. A.; Schleyer, P. v. R. Ab Initio Molecular Orbital Theory; John Wiley & Sons, Inc.: New York, 1986.
48. Huzinaga, S. J. Chem. Phys. 1965, 42, 1293.
49. Dunning, T. H. J. Chem. Phys. 1970, 53, 2823.
50. 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.
51. Häser, M.; Ahlrichs, R. J. Comput. Chem. 1989, 10, 104. Ahlrichs, R.; Bär, M.; Häser, M.; Horn, H.; Kolmel, C. Chem. Phys. Lett. 1989, 162, 165.
52. Häser, M.; Ahlrichs, R. J. Comput. Chem. 1989, 10, 104. Ahlrichs, R.; Bär, M.; Häser, M.; Horn, H.; Kolmel, C. Chem. Phys. Lett. 1989, 162, 165.
53. McKellar, A. R. W.; Bunker, P. R.; Sears, T. J.; Evenson, K. M.; Saykally, R. J.; Langhoff, S. R. J. Chem. Phys. 1983, 79, 5251.
54. Wolinski, K.; Hinton, J. F.; Pulay, P. J. Am. Chem. Soc. 1990, 112, 8251.
55. Schleyer, P. v. R.; Maerker, C.; Dransfeld, A.; Jiao, H.; Hommes, N. v. E. J. Am. Chem. Soc. 1996, 118, 6317.
56. March, J. Advanced Organic Chemistry, 4th ed.; John Wiley & Sons, Inc.: New York, 1992; p 21.
57. Dorigo, A. E.; Li, Y.; Houk, K. N. J. Am. Chem. Soc. 1989, 111, 6942.
58. For the latest detailed study on the cyclopropylidene PES see: Bettinger, H.; Schreiner, P. R.; Schleyer, P. v. R.; Schaefer, H. F. J. Phys. Chem. 1996, 100, 16147.
59. ST and the ESR zero-field parameter \E\lhc has been described in: Largan, J. G.; Sitzmann, E. V.; Eisenthal, K. B. Chem. Phys. Lett. 1984, 110, 521.
60. (a) Balci, M.; Winchester, W. R.; Jones, W. M. J. Org. Chem. 1982, 47, 5180.
61. (b) Tyner, R. L.; Jones, W. M.; Öhrn, Y.; Sabin, J. R. J. Am. Chem. Soc. 1974, 96, 3765.
62. (a) Wittig, G.; Meske-Schüller, I. Liebigs Ann. Chem. 1968, 711, 65.
63. (b) Wittig, G.; Krebs, A.; Pohlke, A. Angew. Chem. 1960, 72, 324.
64. (c) Meier, H.; Molz, T.; Merkle, U.; Echter, T.; Lorch, M. Liebigs Ann. Chem. 1982, 914.
65. (a) Maier, J.; Layer, M.; Combrink, W.; Schniepp, S. Chem. Ber. 1976, 109, 1650.
66. (b) Wittig, G.; Heyn, H. Chem. Ber. 1964, 97, 1609.
67. 8 which do not resemble a naphthyl moiety.
68. Wentrup, C.; Mayor, C.; Becker, J.; Lindner, H. J. Tetrahedron 1985, 41, 1601.
69. Schleyer, P. v. R.; Giao, H. Pure Appl. Chem. 1996, 68, 209.