Nature of methyl and silyl mesolytic dissociations in substituted cyclopropenyl radical cations and anions. A CAS-MCSCF and CCSD(T) theoretical study

Journal of Organic Chemistry

Volumn 64, Issue 11, 1999, Pages 3867-3877

  Carra, Claudio ^a   Fiussello, Francesco ^a   Tonachini, Glauco ^a  

^a UNIVERSITY OF TURIN   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

ANION; CATION; CYCLOPROPANE DERIVATIVE; METHYL GROUP; RADICAL;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; DISSOCIATION; MOLECULAR DYNAMICS; MOLECULAR INTERACTION; PHYSICAL CHEMISTRY; REACTION ANALYSIS;

EID: 0033612394     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo982103u     Document Type: Article

References (50)

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34. (a) Coester, F.; Kümmel, H. Nucl. Phys. 1960, 17, 477. Cízek, J. J. Chem. Phys. 1966, 45, 650-654. Paldus, J.; Cízek, J.; Shavitt, I Phys. Rev. A 1972, 5, 50-67. Pople, J. A.; Krishnan, R.; Schlegel, H. B.; Binkley, J. S. Int. J. Quantum Chem. 1978, 14, 545-560. Bartlett, R. J.; Purvis, G. D. Int. J. Quantum Chem. 1978, 14, 561-581. Cízek, J.; Paldus, J. Phys. Script. 1980, 21, 251-254. Bartlett, R. J. Annu. Rev. Phys. Chem. 1981, 32, 359-401. Purvis, G. D.; Bartlett, R. J. J. Chem. Phys. 1982, 76, 1910-1918. Scuseria, G. E.; Janssen, C. L.; Schaefer, H. F., III. J. Chem. Phys. 1988, 89, 7382-7387. Scuseria, G. E.; Schaefer, H. F., III. J. Chem. Phys. 1989, 90, 3700-3703.
35. (a) Coester, F.; Kümmel, H. Nucl. Phys. 1960, 17, 477. Cízek, J. J. Chem. Phys. 1966, 45, 650-654. Paldus, J.; Cízek, J.; Shavitt, I Phys. Rev. A 1972, 5, 50-67. Pople, J. A.; Krishnan, R.; Schlegel, H. B.; Binkley, J. S. Int. J. Quantum Chem. 1978, 14, 545-560. Bartlett, R. J.; Purvis, G. D. Int. J. Quantum Chem. 1978, 14, 561-581. Cízek, J.; Paldus, J. Phys. Script. 1980, 21, 251-254. Bartlett, R. J. Annu. Rev. Phys. Chem. 1981, 32, 359-401. Purvis, G. D.; Bartlett, R. J. J. Chem. Phys. 1982, 76, 1910-1918. Scuseria, G. E.; Janssen, C. L.; Schaefer, H. F., III. J. Chem. Phys. 1988, 89, 7382-7387. Scuseria, G. E.; Schaefer, H. F., III. J. Chem. Phys. 1989, 90, 3700-3703.
36. (a) Coester, F.; Kümmel, H. Nucl. Phys. 1960, 17, 477. Cízek, J. J. Chem. Phys. 1966, 45, 650-654. Paldus, J.; Cízek, J.; Shavitt, I Phys. Rev. A 1972, 5, 50-67. Pople, J. A.; Krishnan, R.; Schlegel, H. B.; Binkley, J. S. Int. J. Quantum Chem. 1978, 14, 545-560. Bartlett, R. J.; Purvis, G. D. Int. J. Quantum Chem. 1978, 14, 561-581. Cízek, J.; Paldus, J. Phys. Script. 1980, 21, 251-254. Bartlett, R. J. Annu. Rev. Phys. Chem. 1981, 32, 359-401. Purvis, G. D.; Bartlett, R. J. J. Chem. Phys. 1982, 76, 1910-1918. Scuseria, G. E.; Janssen, C. L.; Schaefer, H. F., III. J. Chem. Phys. 1988, 89, 7382-7387. Scuseria, G. E.; Schaefer, H. F., III. J. Chem. Phys. 1989, 90, 3700-3703.
37. (a) Coester, F.; Kümmel, H. Nucl. Phys. 1960, 17, 477. Cízek, J. J. Chem. Phys. 1966, 45, 650-654. Paldus, J.; Cízek, J.; Shavitt, I Phys. Rev. A 1972, 5, 50-67. Pople, J. A.; Krishnan, R.; Schlegel, H. B.; Binkley, J. S. Int. J. Quantum Chem. 1978, 14, 545-560. Bartlett, R. J.; Purvis, G. D. Int. J. Quantum Chem. 1978, 14, 561-581. Cízek, J.; Paldus, J. Phys. Script. 1980, 21, 251-254. Bartlett, R. J. Annu. Rev. Phys. Chem. 1981, 32, 359-401. Purvis, G. D.; Bartlett, R. J. J. Chem. Phys. 1982, 76, 1910-1918. Scuseria, G. E.; Janssen, C. L.; Schaefer, H. F., III. J. Chem. Phys. 1988, 89, 7382-7387. Scuseria, G. E.; Schaefer, H. F., III. J. Chem. Phys. 1989, 90, 3700-3703.
38. (a) Coester, F.; Kümmel, H. Nucl. Phys. 1960, 17, 477. Cízek, J. J. Chem. Phys. 1966, 45, 650-654. Paldus, J.; Cízek, J.; Shavitt, I Phys. Rev. A 1972, 5, 50-67. Pople, J. A.; Krishnan, R.; Schlegel, H. B.; Binkley, J. S. Int. J. Quantum Chem. 1978, 14, 545-560. Bartlett, R. J.; Purvis, G. D. Int. J. Quantum Chem. 1978, 14, 561-581. Cízek, J.; Paldus, J. Phys. Script. 1980, 21, 251-254. Bartlett, R. J. Annu. Rev. Phys. Chem. 1981, 32, 359-401. Purvis, G. D.; Bartlett, R. J. J. Chem. Phys. 1982, 76, 1910-1918. Scuseria, G. E.; Janssen, C. L.; Schaefer, H. F., III. J. Chem. Phys. 1988, 89, 7382-7387. Scuseria, G. E.; Schaefer, H. F., III. J. Chem. Phys. 1989, 90, 3700-3703.
39. (a) Coester, F.; Kümmel, H. Nucl. Phys. 1960, 17, 477. Cízek, J. J. Chem. Phys. 1966, 45, 650-654. Paldus, J.; Cízek, J.; Shavitt, I Phys. Rev. A 1972, 5, 50-67. Pople, J. A.; Krishnan, R.; Schlegel, H. B.; Binkley, J. S. Int. J. Quantum Chem. 1978, 14, 545-560. Bartlett, R. J.; Purvis, G. D. Int. J. Quantum Chem. 1978, 14, 561-581. Cízek, J.; Paldus, J. Phys. Script. 1980, 21, 251-254. Bartlett, R. J. Annu. Rev. Phys. Chem. 1981, 32, 359-401. Purvis, G. D.; Bartlett, R. J. J. Chem. Phys. 1982, 76, 1910-1918. Scuseria, G. E.; Janssen, C. L.; Schaefer, H. F., III. J. Chem. Phys. 1988, 89, 7382-7387. Scuseria, G. E.; Schaefer, H. F., III. J. Chem. Phys. 1989, 90, 3700-3703.
40. (a) Coester, F.; Kümmel, H. Nucl. Phys. 1960, 17, 477. Cízek, J. J. Chem. Phys. 1966, 45, 650-654. Paldus, J.; Cízek, J.; Shavitt, I Phys. Rev. A 1972, 5, 50-67. Pople, J. A.; Krishnan, R.; Schlegel, H. B.; Binkley, J. S. Int. J. Quantum Chem. 1978, 14, 545-560. Bartlett, R. J.; Purvis, G. D. Int. J. Quantum Chem. 1978, 14, 561-581. Cízek, J.; Paldus, J. Phys. Script. 1980, 21, 251-254. Bartlett, R. J. Annu. Rev. Phys. Chem. 1981, 32, 359-401. Purvis, G. D.; Bartlett, R. J. J. Chem. Phys. 1982, 76, 1910-1918. Scuseria, G. E.; Janssen, C. L.; Schaefer, H. F., III. J. Chem. Phys. 1988, 89, 7382-7387. Scuseria, G. E.; Schaefer, H. F., III. J. Chem. Phys. 1989, 90, 3700-3703.
41. (b) While CAS-MCSCF calculations are expected to provide qualitatively reliable geometries through the inclusion of a significant share of the structure-dependent (nondynamical) correlation energy, CCSD(T) energy evaluations should be more liable for assessing energy differences by inclusion of the dynamical contribution to the correlation energy. It must be prudently kept in mind, however, that performing single-point energy calculations, although usual, is in fact a rather rough probing of the higher-level energy hypersurface. This remark is particularly reasonable in the case of the transition structures.
42. GAUSSIAN94: Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Gill, P. M. W.; Johnson, B. G.; Robb, M. A.; Cheeseman, J. R.; Keith, T. A.; Petersson, G. A.; Montgomery, J. A.; Raghavachari, K.; Al-Laham, M. A.; Zakrzewski, V. G.; Ortiz, J. W.; 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. Gaussian, Inc., Pittsburgh, PA, 1995.
43. Compare the configuration mixing scheme of Shaik and Pross, which is formulated in VB terms, e.g., in: Pross, A. Theoretical and Physical Principles of Organic Reactivity; John Wiley & Sons: New York, 1995; pp 109-121 (and references therein). Shaik, S. S.; Hiberty, P. C. Adv. Quantum Chem. 1995, 26, 99-163. See also, for instance: Shaik, S. S. J. Am. Chem. Soc. 1981, 103, 3692-3701. Shaik, S. S.; Pross, A. J. Am. Chem. Soc. 1989, 111, 4306-4312. Shaik, S. S.; Dinnocenzo, J. P. J. Org. Chem. 1990, 55, 3434-3436. Shaik, S.; Reddy, A. C. J. Chem. Soc., Faraday Trans. 1994, 90, 1631-1642. The description provided here derives, of course, from the results of the CAS-MCSCF calculations, which are in MO terms.
44. Compare the configuration mixing scheme of Shaik and Pross, which is formulated in VB terms, e.g., in: Pross, A. Theoretical and Physical Principles of Organic Reactivity; John Wiley & Sons: New York, 1995; pp 109-121 (and references therein). Shaik, S. S.; Hiberty, P. C. Adv. Quantum Chem. 1995, 26, 99-163. See also, for instance: Shaik, S. S. J. Am. Chem. Soc. 1981, 103, 3692-3701. Shaik, S. S.; Pross, A. J. Am. Chem. Soc. 1989, 111, 4306-4312. Shaik, S. S.; Dinnocenzo, J. P. J. Org. Chem. 1990, 55, 3434-3436. Shaik, S.; Reddy, A. C. J. Chem. Soc., Faraday Trans. 1994, 90, 1631-1642. The description provided here derives, of course, from the results of the CAS-MCSCF calculations, which are in MO terms.
45. Compare the configuration mixing scheme of Shaik and Pross, which is formulated in VB terms, e.g., in: Pross, A. Theoretical and Physical Principles of Organic Reactivity; John Wiley & Sons: New York, 1995; pp 109-121 (and references therein). Shaik, S. S.; Hiberty, P. C. Adv. Quantum Chem. 1995, 26, 99-163. See also, for instance: Shaik, S. S. J. Am. Chem. Soc. 1981, 103, 3692-3701. Shaik, S. S.; Pross, A. J. Am. Chem. Soc. 1989, 111, 4306-4312. Shaik, S. S.; Dinnocenzo, J. P. J. Org. Chem. 1990, 55, 3434-3436. Shaik, S.; Reddy, A. C. J. Chem. Soc., Faraday Trans. 1994, 90, 1631-1642. The description provided here derives, of course, from the results of the CAS-MCSCF calculations, which are in MO terms.
46. Compare the configuration mixing scheme of Shaik and Pross, which is formulated in VB terms, e.g., in: Pross, A. Theoretical and Physical Principles of Organic Reactivity; John Wiley & Sons: New York, 1995; pp 109-121 (and references therein). Shaik, S. S.; Hiberty, P. C. Adv. Quantum Chem. 1995, 26, 99-163. See also, for instance: Shaik, S. S. J. Am. Chem. Soc. 1981, 103, 3692-3701. Shaik, S. S.; Pross, A. J. Am. Chem. Soc. 1989, 111, 4306-4312. Shaik, S. S.; Dinnocenzo, J. P. J. Org. Chem. 1990, 55, 3434-3436. Shaik, S.; Reddy, A. C. J. Chem. Soc., Faraday Trans. 1994, 90, 1631-1642. The description provided here derives, of course, from the results of the CAS-MCSCF calculations, which are in MO terms.
47. Compare the configuration mixing scheme of Shaik and Pross, which is formulated in VB terms, e.g., in: Pross, A. Theoretical and Physical Principles of Organic Reactivity; John Wiley & Sons: New York, 1995; pp 109-121 (and references therein). Shaik, S. S.; Hiberty, P. C. Adv. Quantum Chem. 1995, 26, 99-163. See also, for instance: Shaik, S. S. J. Am. Chem. Soc. 1981, 103, 3692-3701. Shaik, S. S.; Pross, A. J. Am. Chem. Soc. 1989, 111, 4306-4312. Shaik, S. S.; Dinnocenzo, J. P. J. Org. Chem. 1990, 55, 3434-3436. Shaik, S.; Reddy, A. C. J. Chem. Soc., Faraday Trans. 1994, 90, 1631-1642. The description provided here derives, of course, from the results of the CAS-MCSCF calculations, which are in MO terms.
48. Compare the configuration mixing scheme of Shaik and Pross, which is formulated in VB terms, e.g., in: Pross, A. Theoretical and Physical Principles of Organic Reactivity; John Wiley & Sons: New York, 1995; pp 109-121 (and references therein). Shaik, S. S.; Hiberty, P. C. Adv. Quantum Chem. 1995, 26, 99-163. See also, for instance: Shaik, S. S. J. Am. Chem. Soc. 1981, 103, 3692-3701. Shaik, S. S.; Pross, A. J. Am. Chem. Soc. 1989, 111, 4306-4312. Shaik, S. S.; Dinnocenzo, J. P. J. Org. Chem. 1990, 55, 3434-3436. Shaik, S.; Reddy, A. C. J. Chem. Soc., Faraday Trans. 1994, 90, 1631-1642. The description provided here derives, of course, from the results of the CAS-MCSCF calculations, which are in MO terms.
49. The reactant geometry in the excited S state was determined only with the 6-31G(d) basis set; with the addition of sp diffuse functions (6-31+G(d) basis set), the MCSCF procedure failed to converge in the reactant zone (distance < 2.4 Å).
50. Salem, L. Electrons in Chemical Reactions. First Principles; J. Wiley & Sons: New York, 1982; pp 141-143 and 148-151.