Perturbations in aromatic and antiaromatic characters due to deuteration: The case of [16]annulene [14]

Journal of the American Chemical Society

Volumn 121, Issue 7, 1999, Pages 1623-1624

  Stevenson, Cheryl D ^a   Kurth, Todd L ^a  

^a ILLINOIS STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANNULENE DERIVATIVE; AROMATIC COMPOUND; DEUTERIUM;

CHEMICAL BOND; CHEMICAL MODIFICATION; ISOMER; LETTER; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SYNTHESIS;

EID: 0033599352     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja983762r     Document Type: Letter

References (25)

1. (a) Strauss, H. L.; Katz, T. J.; Fraenkel, G. K. J. Am. Chem. Soc. 1963, 85, 2360.
2. (b) Stevenson, C. D.; Brown, E. C.; Horvat, D. A.; Borden, W. T. J. Am. Chem. Soc. 1998, 120, 8864.
3. (c) Hrovat, D. A.; Hammons, J. A.; Stevenson, C. D.; Borden, W. T. J. Am. Chem. Soc. 1997, 119, 9523.
4. (d) Moore, J. C.; Thorton, C.; Colleir, W. B.; Devlin, J. P. J. Phys. Chem. 1981, 85, 350.
5. (e) Miller, F. A. J. Chem. Phys. 1956, 24, 996.
6. For example, see: (a) Stevenson C. D.; McElheny, D. J.; Kage, D. E.; Ciszewski, J. T. Reiter, R. C. Anal. Chem. 1998, 70, 3880. (b) Hrovat, D. A.; Hammons, J. A.; Stevenson, C. D.; Borden, W. T. J. Am. Chem. Soc. 1997, 119, 9523. (c) Stevenson, C. D.; Halvorsen T. D.; Reiter, R. C. J. Am. Chem. Soc. 1993, 115, 12405. (d) Stevenson, C. D.; Rice, C. V. J. Am. Chem. Soc. 1995, 117, 10551.
7. For example, see: (a) Stevenson C. D.; McElheny, D. J.; Kage, D. E.; Ciszewski, J. T. Reiter, R. C. Anal. Chem. 1998, 70, 3880. (b) Hrovat, D. A.; Hammons, J. A.; Stevenson, C. D.; Borden, W. T. J. Am. Chem. Soc. 1997, 119, 9523. (c) Stevenson, C. D.; Halvorsen T. D.; Reiter, R. C. J. Am. Chem. Soc. 1993, 115, 12405. (d) Stevenson, C. D.; Rice, C. V. J. Am. Chem. Soc. 1995, 117, 10551.
8. For example, see: (a) Stevenson C. D.; McElheny, D. J.; Kage, D. E.; Ciszewski, J. T. Reiter, R. C. Anal. Chem. 1998, 70, 3880. (b) Hrovat, D. A.; Hammons, J. A.; Stevenson, C. D.; Borden, W. T. J. Am. Chem. Soc. 1997, 119, 9523. (c) Stevenson, C. D.; Halvorsen T. D.; Reiter, R. C. J. Am. Chem. Soc. 1993, 115, 12405. (d) Stevenson, C. D.; Rice, C. V. J. Am. Chem. Soc. 1995, 117, 10551.
9. For example, see: (a) Stevenson C. D.; McElheny, D. J.; Kage, D. E.; Ciszewski, J. T. Reiter, R. C. Anal. Chem. 1998, 70, 3880. (b) Hrovat, D. A.; Hammons, J. A.; Stevenson, C. D.; Borden, W. T. J. Am. Chem. Soc. 1997, 119, 9523. (c) Stevenson, C. D.; Halvorsen T. D.; Reiter, R. C. J. Am. Chem. Soc. 1993, 115, 12405. (d) Stevenson, C. D.; Rice, C. V. J. Am. Chem. Soc. 1995, 117, 10551.
10. The [16]annulene was previously synthesized in our laboratory, see: Stevenson, C. D.; Forch, B. E. J. Am. Chem. Soc. 1980, 102, 5985.
11. Huckel, E. Z. Physik. 1931, 70, 20.
12. (b) Huckel, E. Z. Electrokhim. 1937, 43, 752.
13. (a) Minkin, V. I.; Glukhovtsev, M. N.; Simkin, B. Y. Aromaticity and Antiaromaticity Electronic and Structural Aspects; John Wiley and Sons: New York, 1994.
14. (b) Gunther, H. NMR Spectroscopy, An Introduction; Wiley: New York, 1980.
15. (c) Stevenson, C. D. In Molecular Structure and Energetics; Liebman, J. F., Greenberg, A., Eds.; VCH Publishers: New York, 1986; Vol. 3.
16. Garratt, P. J. Aromaticity, McGraw-Hill: London, 1971.
17. At -140 °C Oth measured chemical shifts of 10.61 ppm for the internal protons, and 5.3 ppm for the external protons at 60 MHz, see: (a) Oth, J. F. M. Pure Appl. Chem. 1971, 25, 573. (b) Oth, J. F. M.; Baumann, H.; Gilles, J.-M; Schroder, G. J. Am. Chem. Soc. 1972, 94, 3498.
18. At -140 °C Oth measured chemical shifts of 10.61 ppm for the internal protons, and 5.3 ppm for the external protons at 60 MHz, see: (a) Oth, J. F. M. Pure Appl. Chem. 1971, 25, 573. (b) Oth, J. F. M.; Baumann, H.; Gilles, J.-M; Schroder, G. J. Am. Chem. Soc. 1972, 94, 3498.
19. (a) Perdeuterated cyclooctatetraene was prepared as described in: Stevenson, C. D.; Burton, R. D.; Reiter, R. C. J. Am. Chem. Soc. 1992, 114, 399. (b) Cyclooctatetraene was dimerized to form the 2 + 2 dimer, which was in turn photolyzed to yield [16]annulene as described in: Schroder, G.; Kirsch, G.; Oth, F, M. Chem. Ber. 1974, 107, 460.
20. (a) Perdeuterated cyclooctatetraene was prepared as described in: Stevenson, C. D.; Burton, R. D.; Reiter, R. C. J. Am. Chem. Soc. 1992, 114, 399. (b) Cyclooctatetraene was dimerized to form the 2 + 2 dimer, which was in turn photolyzed to yield [16]annulene as described in: Schroder, G.; Kirsch, G.; Oth, F, M. Chem. Ber. 1974, 107, 460.
21. 1H chemical shift of cyclooctatetraene due to heptadeuteration is -0.010 ppm.
22. (a) For naphthalene, X-ray crystallography reveals a reduction of the C-L (L = H or D) bond length from 1.085 (C-H) to 1.073 (C-D) Å see: Berger, S.; Kunzer, H. Tetrahedron 1983, 39, 1327. (b) For another cases of isotopic bond length reduction, see: Bartell, L. S.; Roth, E. A.; Hollowell, C. D. J. Chem. Phys. 1965, 42, 2683 and Melander, L.; Saunders, W. H. Reaction Rates of Isotopic Molecules; Wiley: New York, 1980; pp 189-197.
23. (a) For naphthalene, X-ray crystallography reveals a reduction of the C-L (L = H or D) bond length from 1.085 (C-H) to 1.073 (C-D) Å see: Berger, S.; Kunzer, H. Tetrahedron 1983, 39, 1327. (b) For another cases of isotopic bond length reduction, see: Bartell, L. S.; Roth, E. A.; Hollowell, C. D. J. Chem. Phys. 1965, 42, 2683 and Melander, L.; Saunders, W. H. Reaction Rates of Isotopic Molecules; Wiley: New York, 1980; pp 189-197.
24. (a) For naphthalene, X-ray crystallography reveals a reduction of the C-L (L = H or D) bond length from 1.085 (C-H) to 1.073 (C-D) Å see: Berger, S.; Kunzer, H. Tetrahedron 1983, 39, 1327. (b) For another cases of isotopic bond length reduction, see: Bartell, L. S.; Roth, E. A.; Hollowell, C. D. J. Chem. Phys. 1965, 42, 2683 and Melander, L.; Saunders, W. H. Reaction Rates of Isotopic Molecules; Wiley: New York, 1980; pp 189-197.
25. This treatment of deuterated systems is similar to that used by: Zuilhof, H.; Lodder, G.; van Mill, R. P.; Mulder, P. P. J.; Kage, D. E.; Reiter, R. C.; Stevenson, C. D. J. Phys. Chem. 1995, 99, 3461.