Distonic biradical anions. Synthesis and characterization of the 3,5-dehydrophenyl and 1,3,5-trimethylenebenzene negative ions

Journal of the American Chemical Society

Volumn 118, Issue 24, 1996, Pages 5816-5817

  Hu, Jun ^a   Squires, Robert R ^a  

^a PURDUE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BENZENE DERIVATIVE;

ARTICLE; IONIZATION; TECHNIQUE;

EID: 0030017688     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja960756r     Document Type: Article

References (50)

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34. For examples of spin-state specific reactivity differences for biradicals, see: (a) Berson, J. A. In Diradicals; Borden, W. T., Ed.; Wiley-Interscience: New York, 1982; Chapter 4. (b) Inglin, T. A.; Berson, J. A. J. Am. Chem. Soc. 1986, 108, 3394. (c) Stone, K. J.; Greenberg, M. M.; Blackstock, S. C.; Berson, J. A. J. Am. Chem. Soc. 1989, 111, 3659. (d) Adam, W.; Grabowski, S.; Wilson, R. M. Acc. Chem. Res. 1990, 23, 165. (e) Adam, W.; Finzel, R. J. Am. Chem. Soc. 1992, 114, 4563. For precautionary comments, see: (f) Heath, R. B.; Bush, L. C.; Fang, X.-W.; Berson, J. A.; Scaiano, J. C.; Berinstain, A. B. J. Phys. Chem. 1993, 97, 13355. (g) Gajewski, J. J. et al., ref 11(d).
35. For examples of spin-state specific reactivity differences for biradicals, see: (a) Berson, J. A. In Diradicals; Borden, W. T., Ed.; Wiley-Interscience: New York, 1982; Chapter 4. (b) Inglin, T. A.; Berson, J. A. J. Am. Chem. Soc. 1986, 108, 3394. (c) Stone, K. J.; Greenberg, M. M.; Blackstock, S. C.; Berson, J. A. J. Am. Chem. Soc. 1989, 111, 3659. (d) Adam, W.; Grabowski, S.; Wilson, R. M. Acc. Chem. Res. 1990, 23, 165. (e) Adam, W.; Finzel, R. J. Am. Chem. Soc. 1992, 114, 4563. For precautionary comments, see: (f) Heath, R. B.; Bush, L. C.; Fang, X.-W.; Berson, J. A.; Scaiano, J. C.; Berinstain, A. B. J. Phys. Chem. 1993, 97, 13355. (g) Gajewski, J. J. et al., ref 11(d).
36. For examples of spin-state specific reactivity differences for biradicals, see: (a) Berson, J. A. In Diradicals; Borden, W. T., Ed.; Wiley-Interscience: New York, 1982; Chapter 4. (b) Inglin, T. A.; Berson, J. A. J. Am. Chem. Soc. 1986, 108, 3394. (c) Stone, K. J.; Greenberg, M. M.; Blackstock, S. C.; Berson, J. A. J. Am. Chem. Soc. 1989, 111, 3659. (d) Adam, W.; Grabowski, S.; Wilson, R. M. Acc. Chem. Res. 1990, 23, 165. (e) Adam, W.; Finzel, R. J. Am. Chem. Soc. 1992, 114, 4563. For precautionary comments, see: (f) Heath, R. B.; Bush, L. C.; Fang, X.-W.; Berson, J. A.; Scaiano, J. C.; Berinstain, A. B. J. Phys. Chem. 1993, 97, 13355. (g) Gajewski, J. J. et al., ref 11(d).
37. For examples of spin-state specific reactivity differences for biradicals, see: (a) Berson, J. A. In Diradicals; Borden, W. T., Ed.; Wiley-Interscience: New York, 1982; Chapter 4. (b) Inglin, T. A.; Berson, J. A. J. Am. Chem. Soc. 1986, 108, 3394. (c) Stone, K. J.; Greenberg, M. M.; Blackstock, S. C.; Berson, J. A. J. Am. Chem. Soc. 1989, 111, 3659. (d) Adam, W.; Grabowski, S.; Wilson, R. M. Acc. Chem. Res. 1990, 23, 165. (e) Adam, W.; Finzel, R. J. Am. Chem. Soc. 1992, 114, 4563. For precautionary comments, see: (f) Heath, R. B.; Bush, L. C.; Fang, X.-W.; Berson, J. A.; Scaiano, J. C.; Berinstain, A. B. J. Phys. Chem. 1993, 97, 13355. (g) Gajewski, J. J. et al., ref 11(d).
38. For examples of spin-state specific reactivity differences for biradicals, see: (a) Berson, J. A. In Diradicals; Borden, W. T., Ed.; Wiley-Interscience: New York, 1982; Chapter 4. (b) Inglin, T. A.; Berson, J. A. J. Am. Chem. Soc. 1986, 108, 3394. (c) Stone, K. J.; Greenberg, M. M.; Blackstock, S. C.; Berson, J. A. J. Am. Chem. Soc. 1989, 111, 3659. (d) Adam, W.; Grabowski, S.; Wilson, R. M. Acc. Chem. Res. 1990, 23, 165. (e) Adam, W.; Finzel, R. J. Am. Chem. Soc. 1992, 114, 4563. For precautionary comments, see: (f) Heath, R. B.; Bush, L. C.; Fang, X.-W.; Berson, J. A.; Scaiano, J. C.; Berinstain, A. B. J. Phys. Chem. 1993, 97, 13355. (g) Gajewski, J. J. et al., ref 11(d).
39. For examples of spin-state specific reactivity differences for biradicals, see: (a) Berson, J. A. In Diradicals; Borden, W. T., Ed.; Wiley-Interscience: New York, 1982; Chapter 4. (b) Inglin, T. A.; Berson, J. A. J. Am. Chem. Soc. 1986, 108, 3394. (c) Stone, K. J.; Greenberg, M. M.; Blackstock, S. C.; Berson, J. A. J. Am. Chem. Soc. 1989, 111, 3659. (d) Adam, W.; Grabowski, S.; Wilson, R. M. Acc. Chem. Res. 1990, 23, 165. (e) Adam, W.; Finzel, R. J. Am. Chem. Soc. 1992, 114, 4563. For precautionary comments, see: (f) Heath, R. B.; Bush, L. C.; Fang, X.-W.; Berson, J. A.; Scaiano, J. C.; Berinstain, A. B. J. Phys. Chem. 1993, 97, 13355. (g) Gajewski, J. J. et al., ref 11(d).
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42. 2 at 0.45 Torr in the flowing afterglow occurs at about 20% of the collision rate.
43. 2.
44. 2.
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50. triplet) = -12 kcal/mol for 1 and +1.5 kcal/mol for 2. Higher level calculations are in progress.