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Volumn 126, Issue 1, 2004, Pages 237-249

The Rearrangements of Naphthylnitrenes: UV/Vis and IR Spectra of Azirines, Cyclic Ketenimines, and Cyclic Nitrile Ylides

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL BONDS; CHEMICAL RELAXATION; IRRADIATION; ISOMERS; PHOTOLYSIS;

EID: 0345828873     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja038458z     Document Type: Article
Times cited : (66)

References (54)
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    • In the literature, slightly smaller scaling factors of 0.9614 (Scott, A. P.; Radom, L. J. Phys. Chem. 1996, 100, 16502) and 0.9613 (Wong, M. W. Chem. Phys. Lett. 1996, 256, 391) have been proposed. The factor of 0.97 has often given better agreement with experiment in our work on reactive intermediates, which were not part of the "training sets" used in the above studies (cf. e.g.; Pritchina, E. A.; Gritsan, N. P.; Maltsev, A.; Bally, T.; Autrey, T. ; Liu, Y.; Wang, Y.; Toscano, J. P. Phys. Chem. Chem. Phys. 2003, 5, 1010 or Bednarek, P.; Zhu. Z.; Bally, T.; Filipiak, T.; Marcinek, A.; Gebicki, J. J. Am. Chem. Soc. 2001, 123, 2377).
    • (1996) J. Phys. Chem. , vol.100 , pp. 16502
    • Scott, A.P.1    Radom, L.2
  • 32
    • 0030570305 scopus 로고    scopus 로고
    • In the literature, slightly smaller scaling factors of 0.9614 (Scott, A. P.; Radom, L. J. Phys. Chem. 1996, 100, 16502) and 0.9613 (Wong, M. W. Chem. Phys. Lett. 1996, 256, 391) have been proposed. The factor of 0.97 has often given better agreement with experiment in our work on reactive intermediates, which were not part of the "training sets" used in the above studies (cf. e.g.; Pritchina, E. A.; Gritsan, N. P.; Maltsev, A.; Bally, T.; Autrey, T. ; Liu, Y.; Wang, Y.; Toscano, J. P. Phys. Chem. Chem. Phys. 2003, 5, 1010 or Bednarek, P.; Zhu. Z.; Bally, T.; Filipiak, T.; Marcinek, A.; Gebicki, J. J. Am. Chem. Soc. 2001, 123, 2377).
    • (1996) Chem. Phys. Lett. , vol.256 , pp. 391
    • Wong, M.W.1
  • 33
    • 0037444230 scopus 로고    scopus 로고
    • In the literature, slightly smaller scaling factors of 0.9614 (Scott, A. P.; Radom, L. J. Phys. Chem. 1996, 100, 16502) and 0.9613 (Wong, M. W. Chem. Phys. Lett. 1996, 256, 391) have been proposed. The factor of 0.97 has often given better agreement with experiment in our work on reactive intermediates, which were not part of the "training sets" used in the above studies (cf. e.g.; Pritchina, E. A.; Gritsan, N. P.; Maltsev, A.; Bally, T.; Autrey, T. ; Liu, Y.; Wang, Y.; Toscano, J. P. Phys. Chem. Chem. Phys. 2003, 5, 1010 or Bednarek, P.; Zhu. Z.; Bally, T.; Filipiak, T.; Marcinek, A.; Gebicki, J. J. Am. Chem. Soc. 2001, 123, 2377).
    • (2003) Phys. Chem. Chem. Phys. , vol.5 , pp. 1010
    • Pritchina, E.A.1    Gritsan, N.P.2    Maltsev, A.3    Bally, T.4    Autrey, T.5    Liu, Y.6    Wang, Y.7    Toscano, J.P.8
  • 34
    • 0034816335 scopus 로고    scopus 로고
    • In the literature, slightly smaller scaling factors of 0.9614 (Scott, A. P.; Radom, L. J. Phys. Chem. 1996, 100, 16502) and 0.9613 (Wong, M. W. Chem. Phys. Lett. 1996, 256, 391) have been proposed. The factor of 0.97 has often given better agreement with experiment in our work on reactive intermediates, which were not part of the "training sets" used in the above studies (cf. e.g.; Pritchina, E. A.; Gritsan, N. P.; Maltsev, A.; Bally, T.; Autrey, T. ; Liu, Y.; Wang, Y.; Toscano, J. P. Phys. Chem. Chem. Phys. 2003, 5, 1010 or Bednarek, P.; Zhu. Z.; Bally, T.; Filipiak, T.; Marcinek, A.; Gebicki, J. J. Am. Chem. Soc. 2001, 123, 2377).
    • (2001) J. Am. Chem. Soc. , vol.123 , pp. 2377
    • Bednarek, P.1    Zhu, Z.2    Bally, T.3    Filipiak, T.4    Marcinek, A.5    Gebicki, J.6
  • 48
    • 0001413531 scopus 로고    scopus 로고
    • -1 observed for 15. However, due to the different mode mixings which prevail in these different compounds, the positions of these IR bands cannot be directly compared.
    • (1996) J. Org. Chem. , vol.61 , pp. 4351
    • Morawietz, J.1    Sander, W.2
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    • note
    • The reason for the smaller activation energies for cyclization of naphthyl as compared to phenylnitrenes may be due to the fact that the naphthylnitrenes preserve an aromatic ring during this process, whereas the phenylnitrenes do not.
  • 50
    • 33748716611 scopus 로고
    • Section 441
    • For the concept of bond-shift isomers, see: Herges, R. Angew. Chem. Int. Ed. Engl. 1994, 33, 255 (Section 4.4.1).
    • (1994) Angew. Chem. Int. Ed. Engl. , vol.33 , pp. 255
    • Herges, R.1


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