The effect of nitrogen atom on double bond pyramidalization


Ozen R., Guven K., Can H., Balci M.

JOURNAL OF CHEMICAL CRYSTALLOGRAPHY, cilt.34, ss.477-481, 2004 (SCI İndekslerine Giren Dergi) identifier identifier

  • Cilt numarası: 34 Konu: 7
  • Basım Tarihi: 2004
  • Doi Numarası: 10.1023/b:jocc.0000035390.96988.db
  • Dergi Adı: JOURNAL OF CHEMICAL CRYSTALLOGRAPHY
  • Sayfa Sayıları: ss.477-481

Özet

The title compound 6-phenyl-4,6,8-triazatetracyclo[9.2.1.0(2,10).0(4,8)] tetradec-2(10)-ene-5,7-dione ( 6) has been synthesized by the addition of 4-phenyl-1,2,4-triazole-3,5-dione (PTAD) to 2,3-dimethylenebicyclo[2.2.1] heptane. The cell parameters are a = 9.991(5), b = 11.754( 9), c = 6.549( 5) Angstrom, alpha = 101.08( 7)degrees, beta = 103.31( 5)degrees, gamma = 98.24( 5) degrees. The crystal structure of 6 was determined. The obtained geometrical parameters were highly correlated with the DFT calculations. The experimentally determined folding angle of the double bond was found to be 8.44degrees. The effect of the electron-withdrawing ability of nitrogen atom on the degree of pyramidalization is discussed.