Ab initio electronic structure calculations on chlorocarbene-ethylene and chlorocarbene-benzene complexes

Journal of the American Chemical Society

Volumn 121, Issue 26, 1999, Pages 6269-6274

  Krogh Jespersen, Karsten ^a   Yan, Shunqi ^a   Moss, Robert A ^a  

^a RUTGERS UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BENZENE DERIVATIVE; CHLOROCARBENE; SOLVENT; UNCLASSIFIED DRUG;

ARTICLE; COMPLEX FORMATION; DRUG SYNTHESIS; ENTHALPY; ENTROPY; MOLECULAR INTERACTION; REACTION ANALYSIS; STRUCTURE ANALYSIS;

EID: 0033532866     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja990148m     Document Type: Article

References (53)

1. Doering, W. v. E.; Hoffmann, A. K. J. Am. Chem. Soc. 1954, 76, 6162.
2. (a) Moss, R. A. Acc. Chem. Res. 1980, 13, 58.
3. (b) Moss, R. A. Acc. Chem. Res. 1989, 22, 15.
4. (c) Hoffmann, R. J. Am. Chem. Soc. 1968, 90, 1475.
5. (d) Rondan, N. G.; Houk, K. N.; Moss, R. A. J. Am. Chem. Soc. 1980, 102, 1770.
6. Carbene (Carbenoide) Methoden der Organische Chemie (Houben-Weyl); Regitz, M., Ed.; G. Thieme Verlag: Stuttgart, 1989; Vol. E19b, Parts 1 and 2.
7. Turro, N. J.; Lehr, G. F.; Butcher, J. A., Jr.; Moss, R. A.; Guo, W. J. Am. Chem. Soc. 1982, 104, 1754.
8. Moss, R. A.; Perez, L. A.; Turro, N. J.; Gould, I. R.; Hacker, N. P. Tetrahedron Lett. 1983, 24, 685.
9. Eisenthal, K. B.; Moss, R. A.; Turro, N. J. Science 1984, 225, 1439.
10. (a) Houk, K. N.; Rondan, N. G. J. Am. Chem. Soc. 1984, 106, 4293.
11. (b) Houk, K. N.; Rondan, N. G.; Mareda, J. J. Am. Chem. Soc. 1984, 106, 4291.
12. (c) Houk, K. N.; Rondan, N. G.; Mareda, J. Tetrahedron 1985, 41, 1555.
13. Blake, J. F.; Wierschke, S. G.; Jorgensen, W. L. J. Am. Chem. Soc. 1989, 111, 1919.
14. (a) Tomioka, H.; Hayashi, N.; Izawa, Y.; Liu, M. T. H. J. Am. Chem. Soc. 1984, 106, 454.
15. (b) Liu, M. T. H.; Soundararajan, N.; Paike, N.; Subramanian, R. J. Org. Chem. 1987, 52, 4223.
16. (c) Liu, M. T. H. Acc. Chem. Res. 1994, 27, 287.
17. (d) Bonneau, R.; Liu, M. T. H.; Kim, K. C.; Goodman, J. L. J. Am. Chem. Soc. 1996, 118, 3829.
18. Reviews: (a) Moss, R. A. In Advances in Carbene Chemistry; Brinker, U. H., Ed.; JAI Press: Greenwich, CT, 1994; Vol. 1, pp 59f.
19. (b) Bonneau, R.; Liu, M. T. H. In Advances in Carbene Chemistry; Brinker, U. H., Ed.; JAI Press: Stamford, CT, 1998; Vol. 2, pp 1f.
20. (c) Platz, M. S. In Advances in Carbene Chemistry; Brinker, U. H., Ed.; JAI Press: Stamford, CT, 1998; Vol. 2, pp 133f.
21. LaVilla, J. A.; Goodman, J. L. Tetrahedron Lett. 1990, 31, 5109.
22. (a) White, W. R., III; Platz, M. S. J. Org. Chem. 1992, 57, 2841.
23. (b) Modarelli, D. A.; Morgan, S.; Platz, M. S. J. Am. Chem. Soc. 1992, 114, 7034.
24. (c) Nigam, M.; Platz, M. S.; Showalter, B. M.; Toscano, J. P.; Johnson, R.; Abbot, S. C.; Kirchoff, M. M. J. Am. Chem. Soc. 1998, 120, 8055.
25. Hartz, N.; Surya Prakash, G. K.; Olah, G. A. J. Am. Chem. Soc. 1993, 115, 901.
26. Khan, M. I.; Goodman, J. L. J. Am. Chem. Soc. 1995, 117, 6635.
27. Moss, R. A.; Yan, S.; Krogh-Jespersen, K. J. Am. Chem. Soc. 1998, 120, 1088.
28. See also: Ruck, R. T.; Jones, M., Jr. Tetrahedron Lett. 1998, 39, 2277.
29. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Gill, P. M. W.; Johnson, B. G.; Robb, M. A.; Cheeseman, J. R.; Keith, T.; Petersson, 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. J. P.; Head-Gordon, M.; Gonzalez, C.; Pople, J. A. GAUSSIAN 94, Revision E.2; Gaussian, Inc.: Pittsburgh, PA, 1995.
30. Møller, C.; Plesset, M. S. Phys. Rev. 1934, 46, 618.
31. (a) Becke, A. D. J. Chem. Phys. 1993, 98, 5648.
32. (b) Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785.
33. Krishnan, R.; Binkley, J. S.; Seeger, R.; Pople, J. A. J. Chem. Phys. 1980, 72, 650.
34. McLean, A. D.; Chandler, G. S. J. Chem. Phys. 1980, 72, 5639.
35. Clark, T.; Chandrasekhar, J.; Spitznagel, G. W.; Schleyer, P. v. R. J. Comput. Chem. 1983, 4, 294.
36. (a) Boys, S. F.; Bernardi, F. Mol. Phys. 1970, 19, 553.
37. (b) Van Duijnefeldt, F. B.; van Duijneveldt-van de Rijdt, J. G. C. M.; van Lenthe, J. H. Chem. Rev. 1994, 94, 1873.
38. (c) Turi, L.; Dannenberg, J. J. J. Phys. Chem. 1993, 97, 2488.
39. Hehre, W. J.; Radom, L.; Pople, J. A.; Schleyer, P. v. R. Ab Initio Molecular Orbital Theory; Wiley-Interscience: New York, 1986.
40. McQuarrie, D. A. Statistical Thermodynamics; Harper and Row: New York, 1973.
41. Reed, A. E.; Curtiss, L. A.; Weinhold, F. Chem. Rev. 1988, 88, 899.
42. (a) Paizs, B.; Suhai, S. J. Comput. Chem. 1998, 19, 575.
43. (b) Kristyan, S.; Pulay, P. Chem. Phys. Lett. 1994, 229, 175.
44. (c) Perez-Jorda, J. M.; Becke, A. D. Chem. Phys. Lett. 1995, 233, 134.
45. (d) Ruiz, E.; Salahub, D. R.; Vela, A. J. Am. Chem. Soc. 1995, 117, 1141.
46. For recent attempts at describing van der Waals interactions within density functional theory, see for example: Lein, M.; Dobson, J. F.; Gross, E. K. U. J. Comput. Chem. 1999, 20, 12.
47. The stationary points for 4 and 5 remain qualitatively similar to the MP2/6-31G* structures, when even larger basis sets are applied (e.g., MP2/ 6-311+G**).
48. Hammond, G. S. J. Am. Chem. Soc. 1955, 77, 334.
49. Cyclopropane formation also occurs without any activation energy barriers on the B3LYP/6-31G* energy surfaces.
50. We have almost completed a comprehensive (re)investigation of the methylene-benzene energy surface (to be submitted for publication).
51. At the HF/6-31G*//HF/6-31G* level, structure 9b represents, however, a minimum whereas 9a is a transition state. At the B3LYP/6-31G*//B3LYP/6-31G* level, both structures 9a and 9b represent minima.
52. The exact nature of 12a on the MP2/6-31G* surface is not known to us, since we could not perform the required normal-mode analysis, but 12a is a minimum on the B3LYP/6-31G* surface.
53. Enthalpy differences at 298 K may be obtained from the ΔE(MP2-(BSSE,298) values by deducting RT = 0.59 kcal/mol for 1:1 complexes and 2RT= 1.18 kcal/mol for 1:2 complexes.