A theoretical approach to experimental nitration of phenyl and benzyl substituted pyridine-N-oxide derivatives


Tokay N., Ogretir C.

JOURNAL OF MOLECULAR STRUCTURE-THEOCHEM, cilt.629, ss.51-59, 2003 (SCI İndekslerine Giren Dergi) identifier identifier

  • Cilt numarası: 629
  • Basım Tarihi: 2003
  • Doi Numarası: 10.1016/s0166-1280(03)00085-x
  • Dergi Adı: JOURNAL OF MOLECULAR STRUCTURE-THEOCHEM
  • Sayfa Sayıları: ss.51-59

Özet

Quantum chemical calculations of 2-, 3-, and 4-phenyl substituted pyridine-N-oxide derivatives revealed that 2- and 3-phenyl derivatives nitrate via free base mechanism. For 4-phenylpyridine-N-oxide, however, calculations imply conjugated acid mechanism for nitration. For 2- and 4-benzylpyridine-N-oxide molecules a conjugated acid mechanism were suggested in nitration process. Attempts to search a correlation between the experimental acidity constants, pK(a), and computed acidity constants were successful. (C) 2003 Elsevier B.V. All rights reserved.