The estimation of the aromaticity of five-membered and benzo fused five-membered rings by the hybrid DFT computed magnetic properties

Journal of Heterocyclic Chemistry

Volumn 33, Issue 4, 1996, Pages 1079-1081

  Jursic, Branko S ^a  

^a UNIVERSITY OF NEW ORLEANS   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000096991     PISSN: 0022152X     EISSN: None     Source Type: Journal    
DOI: 10.1002/jhet.5570330414     Document Type: Article

References (35)

1. V. J. Minkin, M. N. Glukhovtsev, and B. Y. Simkin, Aromaticity and Antiaromaticity; Electronic and Structural Aspects, Wiley, New York, 1994; P. J. Garratt, Aromaticity, Wiley, New York, 1986.
2. V. J. Minkin, M. N. Glukhovtsev, and B. Y. Simkin, Aromaticity and Antiaromaticity; Electronic and Structural Aspects, Wiley, New York, 1994; P. J. Garratt, Aromaticity, Wiley, New York, 1986.
3. A. R. Katritzky, R. Taylor, Adv. Heterocyclic Chem., 47, 87 (1990); A. R. Katritzky, M. Karelson, and N. Malhorta, Heterocycles, 32, 127 (1991); T. L. Gilchrist, Heterocyclic Chemistry, Pitman, Marshfield, MA, 1985.
4. A. R. Katritzky, R. Taylor, Adv. Heterocyclic Chem., 47, 87 (1990); A. R. Katritzky, M. Karelson, and N. Malhorta, Heterocycles, 32, 127 (1991); T. L. Gilchrist, Heterocyclic Chemistry, Pitman, Marshfield, MA, 1985.
5. A. R. Katritzky, R. Taylor, Adv. Heterocyclic Chem., 47, 87 (1990); A. R. Katritzky, M. Karelson, and N. Malhorta, Heterocycles, 32, 127 (1991); T. L. Gilchrist, Heterocyclic Chemistry, Pitman, Marshfield, MA, 1985.
6. N. C. Baird, J. Chem. Educ., 48, 509 (1971).
7. P. George, M. Trachman, C. W. Bock, and A. M. Brett, J. Chem. Soc., Perkin Trans. 2, 1222 (1976); P. George, M. Trachman, C. W. Bock, and A. M. Brett, Tetrahedron, 32, 1357 (1976).
8. P. George, M. Trachman, C. W. Bock, and A. M. Brett, J. Chem. Soc., Perkin Trans. 2, 1222 (1976); P. George, M. Trachman, C. W. Bock, and A. M. Brett, Tetrahedron, 32, 1357 (1976).
9. R. C. Haddon, J. Am. Chem. Soc., 101, 1722 (1979); J. Aihara, J. Am. Chem. Soc., 103, 5704, 1981.
10. R. C. Haddon, J. Am. Chem. Soc., 101, 1722 (1979); J. Aihara, J. Am. Chem. Soc., 103, 5704, 1981.
11. Gaussian 94, Revision B.3; 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, 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.
12. A. D. Becke, J. Chem. Phys., 98, 5648 (1993).
13. C. Lee, W. Yang, and R. G. Parr, Phys. Rev. B, 37, 785 (1988).
14. T. A. Keith and R. F. W. Bader, Chem. Phys. Letters, 210, 223 (1993); T. A. Keith and R. F. W. Bader, Chem. Phys. Letters, 194, 1 (1992).
15. T. A. Keith and R. F. W. Bader, Chem. Phys. Letters, 210, 223 (1993); T. A. Keith and R. F. W. Bader, Chem. Phys. Letters, 194, 1 (1992).
16. For the gaussian basis sets see: J. B. Foresman and Æ. Frisch, Exploring Chemistry with Electronic Structure Methods: A Guide to Using Gaussian, Gaussian, Inc., Pittsburgh, PA, 1993.
17. B. S. Jursic and Z. Zdravkovski, Int. J. Quant. Chem., 54, 161 (1994); B. S. Jursic, Chem. Phys. Letters, 236, 206 (1995); B. S. Jursic and Z. Zdravkovski, J. Chem. Soc., 1223 (1995); B. S. Jursic, J. Org. Chem., 60, 4721 (1995).
18. B. S. Jursic and Z. Zdravkovski, Int. J. Quant. Chem., 54, 161 (1994); B. S. Jursic, Chem. Phys. Letters, 236, 206 (1995); B. S. Jursic and Z. Zdravkovski, J. Chem. Soc., 1223 (1995); B. S. Jursic, J. Org. Chem., 60, 4721 (1995).
19. B. S. Jursic and Z. Zdravkovski, Int. J. Quant. Chem., 54, 161 (1994); B. S. Jursic, Chem. Phys. Letters, 236, 206 (1995); B. S. Jursic and Z. Zdravkovski, J. Chem. Soc., 1223 (1995); B. S. Jursic, J. Org. Chem., 60, 4721 (1995).
20. B. S. Jursic and Z. Zdravkovski, Int. J. Quant. Chem., 54, 161 (1994); B. S. Jursic, Chem. Phys. Letters, 236, 206 (1995); B. S. Jursic and Z. Zdravkovski, J. Chem. Soc., 1223 (1995); B. S. Jursic, J. Org. Chem., 60, 4721 (1995).
21. For thiophene see: B. Back, D. Christensen, L. Hansen-Nygaard, J. RastrupAndersen, J. Mol. Spectrosc., 7, 58 (1961); For pyrrole see: L. Hansen-Nygaard, J. T. Nielsen, J. Kirchheiner, G. Maltesen, J. Rastrup-Andersen, and G. O. Sørensen, J. Mol. Struct., 3, 491 (1969); For furan see: F. Mata, M. C. Martin, and G. O. Sørensen, J. Mol. Struct., 48, 157 (1978).
22. For thiophene see: B. Back, D. Christensen, L. Hansen-Nygaard, J. RastrupAndersen, J. Mol. Spectrosc., 7, 58 (1961); For pyrrole see: L. Hansen-Nygaard, J. T. Nielsen, J. Kirchheiner, G. Maltesen, J. Rastrup-Andersen, and G. O. Sørensen, J. Mol. Struct., 3, 491 (1969); For furan see: F. Mata, M. C. Martin, and G. O. Sørensen, J. Mol. Struct., 48, 157 (1978).
23. For thiophene see: B. Back, D. Christensen, L. Hansen-Nygaard, J. RastrupAndersen, J. Mol. Spectrosc., 7, 58 (1961); For pyrrole see: L. Hansen-Nygaard, J. T. Nielsen, J. Kirchheiner, G. Maltesen, J. Rastrup-Andersen, and G. O. Sørensen, J. Mol. Struct., 3, 491 (1969); For furan see: F. Mata, M. C. Martin, and G. O. Sørensen, J. Mol. Struct., 48, 157 (1978).
24. F. Klages, Chem. Ber., 82, 358 (1949).
25. L. Pauling, The Nature of the Chemical Bond, 3rd Ed, Cornell University Press, Ithaca, N.Y., 1960; O. Bastiansen, L. Fernholt, H. M. Seip, H. Kambara, and K. Kuchitsu, J. Mol. Struct., 18, 163 (1973); K. Tamagawa, T. Iijima, and Y. Kimura, J. Mol. Struct., 30, 243, (1976).
26. L. Pauling, The Nature of the Chemical Bond, 3rd Ed, Cornell University Press, Ithaca, N.Y., 1960; O. Bastiansen, L. Fernholt, H. M. Seip, H. Kambara, and K. Kuchitsu, J. Mol. Struct., 18, 163 (1973); K. Tamagawa, T. Iijima, and Y. Kimura, J. Mol. Struct., 30, 243, (1976).
27. L. Pauling, The Nature of the Chemical Bond, 3rd Ed, Cornell University Press, Ithaca, N.Y., 1960; O. Bastiansen, L. Fernholt, H. M. Seip, H. Kambara, and K. Kuchitsu, J. Mol. Struct., 18, 163 (1973); K. Tamagawa, T. Iijima, and Y. Kimura, J. Mol. Struct., 30, 243, (1976).
28. P. v. R. Schleyer, P. K. Freeman, H. Jiao and B. Goldfuss, Angew. Chem., Int. Ed Engl, 34, 337 (1995).
29. L. F. Fieser and M. J. Haddadin, J. Am. Chem. Soc., 86, 2081 (1964); W. Friedrichsen, Adv. Heterocyclic Chem., 26, 135 (1980).
30. L. F. Fieser and M. J. Haddadin, J. Am. Chem. Soc., 86, 2081 (1964); W. Friedrichsen, Adv. Heterocyclic Chem., 26, 135 (1980).
31. R. McCulloch and A. R. Rye, Tetrahedron Letters, 5231 (1969).
32. D. R. Bender, J. E. Hearst, and H. Rappoport, J. Org. Chem., 44, 2176 (1979).
33. R. J. Sunderberg, Pyrroles and their Benzo Derivatives: (iii) Synthesis and Applications in Comprehensive Heterocyclic Chemistry, A. R. Katritzky and C. W. Ress, eds, Pergoman Press, New York, 1984, Vol 4 part 3, 313.
34. B. S. Jursic, J. Heterocyclic Chem., 32, 1455 (1995); B. S. Jursic, J. Heterocyclic Chem., 32, 1499 (1995).
35. B. S. Jursic, J. Heterocyclic Chem., 32, 1455 (1995); B. S. Jursic, J. Heterocyclic Chem., 32, 1499 (1995).