Quantum chemical studies on the tautomerism of some potentially tautomeric aminoindazole derivatives

Ogretir C., TAY N. F.

STRUCTURAL CHEMISTRY, cilt.17, sa.3, ss.263-274, 2006 (SCI İndekslerine Giren Dergi) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 17 Konu: 3
  • Basım Tarihi: 2006
  • Doi Numarası: 10.1007/s11224-006-9019-z
  • Sayfa Sayıları: ss.263-274


The aqueous phase AM1, PM3, and PM5 calculation data had indicated that when a potentially tautomeric amino group is placed at 3C position of the indazole ring the ring-chain tautomerism becomes feasible. However, when the amino group is placed at 4-7C of the indazole ring only the annular tautomerism was found to be feasible and no effect of amino group to provoke a ring chain tautomerism was observed. On the other hand amino form of 3 amino substituted indazole was found to be predominant over imino forms whereas for the 4-7 amino substituted indazoles imino forms were found to be predominant over amino forms. The attempt to apply soft-hard base and soft nucleophile-electrophile criteria to protonation and tautomerism phenomena was successful.