Semiempirical and Ab Initio Calculations of Tautomerism in 2,3-Dihydroxypyrazine

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Ahmed M. El-Nahas


Abstract

Semiempirical (AM1 and PM3) and ab initio (MP2/6-31+G*//HF/6-31+G*) calculations on the relative stabilities of different tautomers of 2,3-dihydroxypyrazine show that this species exists not only in solution but also in the gas phase predominantly as a dioxo tautomer.


References

  1. M. J. S. Dewar, E. G. Zoebisch, E. F. Healy and J. J. P. Stewart, J. Am. Chem. Soc., 1985, 107, 3902 CrossRef.
  2. J. J. P. Stewart, J. Comput. Chem., 1989, 10, 209, 221 CrossRef CAS.
  3. J. S. Kwaitowski, T. J. Zielinski and R. Rein, Adv. Quant. Chem., 1986, 18, 85 Search PubMed.
  4. W. M. F. Fabian, J. Phys. Org. Chem., 1990, 3, 332 CAS.
  5. W. M. F. Fabian, J. Mol. Struct. (Theochem), 1990, 206, 295 CrossRef.
  6. J. Leszczynski, J. Phys. Chem., 1992, 96, 1649 CrossRef CAS.
  7. H. Meghezzi and A. Boucekkine, J. Mol. Struct. (Theochem), 1992, 257, 175 CrossRef.
  8. U. Narinder, J. Mol. Struct. (Theochem), 1989, 188, 199 CrossRef.
  9. A. R. Katritzky, M. Szafran and J. Stevens, J. Mol. Struct. (Theochem), 1989, 184, 179 CrossRef.
  10. C. Reichardt, in Solvent and Solvent Effects in Organic Chemistry, VCH, Weinheim, 1988 Search PubMed.
  11. G. Rauhut, T. Clark and T. Steinke, J. Am. Chem. Soc., 1993, 115, 9174 CrossRef CAS.
  12. J. G. Contreras and J. B. Alderete, Bol. Soc. Chil. Quim., 1992, 37, 7 Search PubMed.
  13. A. Peeters, C. V. Alesony, A. T. H. Lenstra and H. G. Geise, Int. J. Quant. Chem., 1993, 46, 73 CAS.
  14. G. Rauhut, A. Alex, J. Chandrasekhar and T. Clark, in VAMP5.5, Oxford Molecular Ltd., Oxford, 1993 Search PubMed.
  15. C. C. J. Roothaan, Rev. Mod. Phys., 1951, 23, 69 CrossRef CAS.
  16. (a) P. C. Harriharan and J. A. Pople, Theor. Chim. Acta, 1973, 28, 213 CrossRef CAS; (b) T. Clark, J. Chandrasekhar, G. W. Spitznagel and P. v. R. Schleyer, J. Comput. Chem., 1983, 4, 294 CrossRef CAS.
  17. (a) C. Moeller and M. S. Plesset, Phys. Rev., 1934, 46, 618 CrossRef CAS; (b) J. A. Pople, J. S. Binkley and R. Seeger, Int. J. Quant. Chem., 1976, 10, 1 CAS.
  18. (a) J. Frank and A. R. Katritzky, J. Chem. Soc., Perkin Trans. 2, 1976, 1428 RSC; (b) M. Kuzuya, A. Noguchi and T. Okuda, J. Chem. Soc., Perkin Trans. 2, 1985, 1423 RSC.
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