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Study of Solvent Effects in Diels-Alder Reaction through Charge Transfer Formation by Using Semi-empirical Calculations

  • Shihab, Mehdi Salih (Al-Nahrain University, College of Science, Department of Chemistry, Al-Jadrya, Baghdad-Iraq)
  • Published : 2008.10.20

Abstract

Study of computational model of the concerted Diels-Alder reaction between 9,10-dimethyl anthracene (as donor) and tetracyanoethylene (as acceptor) in absence and in presence of aromatic solvents (benzene, mesitylene and hexamethylbenzene, as donors) using an AM1 semi-empirical method. AM1 method used to study the neutral charge transfer complex models that could be expected between donor and acceptor during the course of the concerted Diels-Alder reaction. Calculated enthalpies of reaction of the charge transfer complexes models showed physical and chemical meaning for explain the effect of aromatic solvents on the kinetic process of concerted Diels-Alder reaction that contains tetracyanoethylene.

Keywords

References

  1. Fujitomo, H.; Inagaki, S.; Fukui, K. J. Am. Chem. Soc. 1976, 98, 2670 https://doi.org/10.1021/ja00425a048
  2. Fukui, K. Science 1982, 218, 747 https://doi.org/10.1126/science.218.4574.747
  3. Haddon, R. C.; Fukunaga, T. Tetrahedron Lett. 1980, 21, 1191 https://doi.org/10.1016/S0040-4039(00)71367-0
  4. Hess, B. A., Jr.; Schaad, L. J. J. Am. Chem. Soc. 1971, 93, 2413 https://doi.org/10.1021/ja00739a008
  5. Zhou, Z.; Parr, R. G. J. Am. Chem. Soc. 1989, 111, 7371 https://doi.org/10.1021/ja00201a014
  6. Okamoto, Y. J. Phys. Chem. B 2001, 105, 1813 https://doi.org/10.1021/jp0028655
  7. Spino, C.; Rezaei, H.; Dory, Y. L. J. Org. Chem. 1998, 63, 5350 https://doi.org/10.1021/jo980090e
  8. Andrews, L. J.; Keefer, R. M. J. Am. Chem. Soc. 1955, 75, 3776
  9. Oshima, T.; Arikata, S.; Nagai, T. J. Chem. Res. 1981, (S) 204, (M) 2518
  10. Kiselev, V. D.; Konovalov, A. I.; Asano, T.; Kashaeva, E. A.; Iskhakova, G. G.; Shihab, M. S.; Medvedeva, M. D. J. Phys. Org. Chem. 2001, 14, 636 https://doi.org/10.1002/poc.398
  11. Hobza, P.; Zahradnik, R. Intermolecular Complexes; Elsevier: Amsterdam, 1988
  12. Foster, R. Organic Charge-Transfer Complexes; Academic press: London, New York, 1969; Molecular Complexes, Foster, R., Ed.; Elek Science: London, 1974/73; Vol. 1 & 2
  13. Gavezzotti, A. Chem. Phys. Lett. 1989, 161, 67 https://doi.org/10.1016/S0009-2614(89)87033-2
  14. Gavezzotti, A.; Desiraju, G. R. Acta Crystallogr. Sect. B Struct. Sci. 1988, 44, 427 https://doi.org/10.1107/S0108768188001600
  15. Mulliken, R. S.; Person, W. B. Molecular Complexes; Wiley Interscience: New York, 1969
  16. Kobinata, S.; Nagakura, S. J. Am. Chem. Soc. 1966, 88, 3905 https://doi.org/10.1021/ja00969a003
  17. Konovalov, A. I.; Kiselev, V. D. Russ. Chem. Bull., Int. Ed. 2003, 52, 293 https://doi.org/10.1023/A:1023486127587
  18. Merrifield, R. E.; Philips, W. D. J. Am. Chem. Soc. 1958, 80, 2778 https://doi.org/10.1021/ja01544a052
  19. Howell, J. O.; Goncalves, J. M.; Amatore, C.; Klasinc, L.; Wightman, R. M.; Kochi, J. K. J. Am. Chem. Soc. 1984, 106, 3968 https://doi.org/10.1021/ja00326a014
  20. Dewar, M. J. S.; Zoebisch, E. G.; Healy, E. F.; Stewart, J. J. P. J. Am. Chem. Soc. 1985, 107, 3902 https://doi.org/10.1021/ja00299a024
  21. Kiselev, V. D.; Miller, J. G. J. Am. Chem. Soc. 1975, 97, 4036 https://doi.org/10.1021/ja00847a028
  22. Greer, L. M.; Blackstock, S. C. J. Org. Chem. 1996, 61, 7895 https://doi.org/10.1021/jo960998+
  23. Thompson, C. C.; de Maine, P. A. D. J. Phys. Chem. 1966, 69, 2766 https://doi.org/10.1021/j100892a048
  24. Reichardt, C. Solvents and Solvent Effects in Organic Chemistry; Wiely-VCH: 2003; Chap. 2
  25. Houk, K. N.; Li, Y.; Evenseck, J. D. Angew. Chem. Int. Ed. Engl. 1992, 31, 682 https://doi.org/10.1002/anie.199206821

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