The Quest for Carbenic Nitrile Imines: Experimental and Computational Characterization of C-Amino Nitrile Imine

Nunes C. M., Reva I., Rosado M. T. S., Fausto R.

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, cilt.2015, sa.34, ss.7484-7493, 2015 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 2015 Sayı: 34
  • Basım Tarihi: 2015
  • Doi Numarası: 10.1002/ejoc.201501153
  • Dergi Adı: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.7484-7493
  • İstanbul Kültür Üniversitesi Adresli: Evet

Özet

C-Amino nitrile imine has been generated as primary photoproduct (lambda = 220 nm) of 5-amino-2H-tetrazole isolated in an argon matrix at 15 K. Subsequent photochemical experiments (lambda = 330 nm) demonstrated that C-amino nitrile imine isomerizes to the corresponding three-membered-ring 1H-diazirine and decomposes to methylenimine. The experimen-tally observed nu(as)(CNN) absorption at 1998 cm(-1) and a carbenic resonance structure contribution of around 20%, predicted by natural resonance theory calculations, demonstrate that the protoproduced C-amino nitrile imine has significant carbenic character. These results pave the way to the discovery of carbenic nitrile imines.