Direct observation of 1,2-didehydronaphthalene in a low temperature argon matrix: consecutive photolysis of 1,2-naphthalenedicarboxylic anhydride

(Note: The full text of this document is currently only available in the PDF Version )

Tadatake Sato, Masaya Moriyama, Hiroyuki Niino and Akira Yabe


Abstract

1,2-Didehydronaphthalene (1-naphthyne) was produced in a low temperature argon matrix by wavelength-selective photolysis of 1,2-naphthalenedicarboxylic anhydride, which was confirmed by comparison of its FTIR spectrum with the theoretical IR spectrum calculated by density functional theory.


References

  1. See, for example: (a) J. G. Radziszewsky, B. A. Hess Jr. and R. Zahradnik, J. Am. Chem. Soc., 1992, 114, 52 CrossRef; (b) J. G. G. Simon, N. Münzel and A. Schweig, Chem. Phys. Lett., 1990, 170, 187 CrossRef CAS; (c) R. Warmuth, Angew. Chem., Int. Ed. Engl., 1997, 36, 1347 CrossRef CAS and references therein.
  2. A. M. Orendt, J. C. Facelli, J. G. Radziszewski, W. J. Horton, D. M. Grant and J. Michl, J. Am. Chem. Soc., 1996, 118, 846 CrossRef CAS.
  3. H. J. Jiao, P. V. R. Schleyer, B. R. Beno, K. N. Houk and R. Warmuth, Angew. Chem., Int. Ed., 1998, 36, 2761.
  4. See, for example: E. Pauzat, D. Talbi and Y. Ellinger, Astron. Astrophys., 1995, 293, 263 Search PubMed; E. Pauzat, D. Talbi and Y. Ellinger, Astron. Astrophys., 1997, 319, 318 Search PubMed; S. R. Langhoff, J. Phys. Chem., 1996, 100, 2819 Search PubMed and references therein.
  5. See, for example, D. M. Hudgins and L. J. Allamandola, J. Phys. Chem. A., 1997, 101, 3472 Search PubMed; S. P. Ekern, A. G. Marshall, J. Szczepanski and M. Vala, J. Phys. Chem. A., 1998, 102, 3498 CrossRef CAS and references therein.
  6. H. A. Weimer, B. J. McFarland, S. Li and W. Weltner Jr., J. Phys. Chem., 1995, 99, 1824 CrossRef CAS.
  7. Gaussian 94, Revision E.2, M. J. Frisch, G. W. Trucks, H. B. Schlegel, P. M. W. Gill, B. G. Johnson, M. A. Robb, J. R. Cheeseman, T. Keith, G. A. Petersson, J. A. Montgomery, K. Raghavachari, M. A. Al-Laham, V. G. Zakrzewski, J. V. Ortiz, J. B. Foresman, J. Cioslowski, B. B. Stefanov, A. Nanayakkara, M. Challacombe, C. Y. Peng, P. Y. Ayala, W. Chen, M. W. Wong, J. L. Andres, E. S. Replogle, R. Gomperts, R. L. Martin, D. J. Fox, J. S. Binkley, D. J. Defrees, J. Baker, J. P. Stewart, M. Head-Gordon, C. Gonzalez, and J. A. Pople, Gaussian, Inc., Pittsburgh PA, 1995.
  8. 1(Armatrix, 11K) UV-VIS (λ/nm): 356, 349, 339, 333, 324, 319, 311, 306, 250, 248, 243, 211. FTIR (/cm–1): 3098vw, 3068vw, 1852m, 1787s, 1461w, 1348w, 1286s, 1182m, 1158w, 1131m, 931m, 896s, 839m, 767m, 747w, 582w, 507w.
  9. J. Lohmann, J. Chem. Soc., Faraday Trans., 1971, 814 RSC.
  10. The quantum yield of the photolysis of 1 isolated in the argon matrix was estimated as ca. 10–4.
  11. 2(Ar matrix, 11 K) UV-VIS (λ/nm): 316, 309, 303, 296, 290, 278, 268, 238s, 231, 225. Observed FTIR bands (/cm–1) and theoreticallypredicted frequencies (cm–1) and intensity (km mol–1) in parentheses: 3047vw, 2074vw, 3084vw (3069, 7; 3080, 16; 3089, 15; 3092, 12), 1832m, 1842m, 1856m, 1872m, (1875, 915; C = Ostr), —(1604, 22), 1579vw (1570, 37), 1568vw (1552, 14), 1510w (1495, 37), 1448vw (1428, 8), 1329vw (1326, 6), —(1316, 8), —(1092, 9), —(967, 6), 820w (809, 39), 774w (763, 8), 748w (737, 20), 645w (664, 25), —(594, 20), 493w (488, 10).
  12. For example: R. F. C. Brown, N. R. Browne, K. J. Coulston, F. W. Eastwood, M. J. Irvine, A. D. E. Pullin and U. E. Wiersum, Aust. J. Chem., 1989, 42, 1321 Search PubMed.
  13. At the computational level, the vibrational frequencies of o-benzyne were predicted with reasonable accuracy. Although some vibrational modes containing the motion of the C[triple bond, length as m-dash]C moiety showed relatively large deviation, the rms deviation between calculated (scaled by 0.961414) and observed1a frequencies was 40.7 cm–1.
  14. Scaling factor for B3LYP/6-31G* level was used: A. P. Scott and L. Radom, J. Phys. Chem., 1996, 100, 16 502 Search PubMed.
  15. M. Moriyama, T. Ohana and A. Yabe, J. Am. Chem. Soc., 1997, 119, 10 229 CrossRef CAS.
  16. R. F. C. Brown, Pure Appl. Chem., 1990, 62, 1981 CAS.
  17. 2-Naphthyne was directly formed from 2,3-naphthalenedicarboxylic anhydride upon irradiation at 266 nm and showed a similar FTIR spectrum to that reported.6.
Click here to see how this site uses Cookies. View our privacy policy here.