Research on Chemical Intermediates

, Volume 26, Issue 4, pp 375–384 | Cite as

A theoretical study on the structure and properties of phenothiazine derivatives and their radical cations

  • Xiao-Song Li
  • Lei Liu
  • Ting-Wei Mu
  • Qing-Xiang Guo
  • You-Cheng Liu


Semiempirical CNDO, AM1, PM3 and ab initio HF/STO-3G, HF/3-21G(d), and HF/6-31(d) methods were employed in the geometry optimization of the phenothiazine and the corresponding radical cation. The results obtained from the PM3 performances were as good as those from the ab initio calculations in the structure optimization of both phenothiazine and phenothiazine radical cation. The PM3 method was used to optimize the structures of a series of N-substituted phenothiazine derivatives and their radical cations. The PM3-optimized results were then analyzed with the ab initio calculation at the 6-311G(d,p) level, which yielded the total energy, frontier molecular orbitals, dipole moments, and charge and spin density distributions of the phenothiazine derivatives and their radical cations.


Dipole Moment Radical Cation Geometry Optimization Phenothiazine Frontier Molecular Orbital 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.


Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.


  1. 1.
    P. Mitchell, Austral. New Zealand J. Psych. 27, 370 (1993).CrossRefGoogle Scholar
  2. 2.
    C.M. Gooley, H. Keyzerr, and F. Setchell, Nature 223, 80 (1969).CrossRefGoogle Scholar
  3. 3.
    W.J. Albery, A.W. Foulds, K.J. Hall, A.R. Hillman, R.G. Edgell, and A.F. Orchard, Nature 282, 793 (1979).CrossRefGoogle Scholar
  4. 4.
    I.I. Abu-Abdoun and A. Ledwith, Eur. Polym. J. 33, 1671 (1997).CrossRefGoogle Scholar
  5. 5.
    T. Yamamura, K. Suzuki, T. Yamaguchi, and T. Nishiyama, Bull, Chem. Soc. Jpn. 70, 413 (1997).CrossRefGoogle Scholar
  6. 6.
    N.J. Turro, I.V. Khudyakov, and H. van Willigen, J. Am. Chem. Soc. 117, 12273 (1995).CrossRefGoogle Scholar
  7. 7.
    E. Bosch and J.K. Kochi, J. Chem. Soc. Perkin Tran. 1 1057 (1995).CrossRefGoogle Scholar
  8. 8.
    S. Nath, H. Pal, D.K. Palit, A.V. Sapre, and J.P. Mittal, J. Phys. Chem. A 102, 5822 (1998).CrossRefGoogle Scholar
  9. 9.
    H.-M. Zhang, X.-Q. Ruan, Q.-X. Guo, and Y.-C. Liu, Res. Chem. Intermed. 24, 687 (1998).CrossRefGoogle Scholar
  10. 10.
    H.-M. Zhang, X.-Q. Ruan, X.-Q. Guo and Y.-C. Liu, Chem. Lett. 449 (1998).Google Scholar
  11. 11.
    D. Clarke, B.C. Gilbert, P. Hanson, C.M. Kirk, J. Chem. Soc. Perkin Trans.2 1103 (1978).Google Scholar
  12. 12.
    X.-Q. Zheng, X.-Q. Ruan, W. Wang, H.-M. Zhang, Q.-X. Guo, and Y.-C. Liu, Bull. Chem. Soc. Jpn. 72, 253 (1999).CrossRefGoogle Scholar
  13. 13.
    S.C. Chu and D.V. Helm, Acta Cryst. B30, 2489 (1974).Google Scholar
  14. 14.
    J.J.H. McDowell, Acta Cryst. B32, 5 (1976).Google Scholar
  15. 15.
    T. Uchida, M. Ito, and K. Kozawa, Bull. Chem. Soc. Jpn. 56, 577 (1983).CrossRefGoogle Scholar
  16. 16.
    M.C. Apreda, F.H. Cano, C. Foces-Foces, F. Lopez-Ruperez, J.C. Conesa, and J. Soria, J. Chem. Soc. Perkin Trans.2 575 (1987).Google Scholar
  17. 17.
    Y.-C. Liu, Y.-B. Ding, and Z.-L. Liu, Acta Chem. Sin. 48, 1199 (1990).Google Scholar
  18. 18.
    Y.-C. Liu, Y.-B. Ding, and Z.-L. Liu, JIEGOUHUAXUE 8, 140 (1989).Google Scholar
  19. 19.
    X.-S. Gao, J.-K. Feng, Q. Jia, Y.-C. Liu, and J.-Z. Sun, Acta Chem. Sin. 54, 1159 (1996).Google Scholar
  20. 20.
    J.-K. Feng, X.-S. Gao, Q. Jia, Y.-C. Liu, and C.-C. Sun, Chem. J. Chin. Univ. 17, 925 (1996).Google Scholar
  21. 21.
    V.K. Turchaninov, A.I. Vokin, and N.N. Chipanina, Russ. Chem. Bull. 47, 8 (1998).CrossRefGoogle Scholar
  22. 22.
    GAUSSIAN 94, Revision B.1, 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.Google Scholar

Copyright information

© VSP 2000

Authors and Affiliations

  • Xiao-Song Li
    • 1
  • Lei Liu
    • 1
  • Ting-Wei Mu
    • 1
  • Qing-Xiang Guo
    • 1
  • You-Cheng Liu
    • 1
  1. 1.Department of Chemistry and CAS Laboratory of Bond-Selective ChemistryUniversity of Science and Technology of ChinaHefeiP.R. China

Personalised recommendations