The effect of nitrogen atom on double bond pyramidalization


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

JOURNAL OF CHEMICAL CRYSTALLOGRAPHY, vol.34, no.7, pp.477-481, 2004 (Journal Indexed in SCI) identifier identifier

  • Publication Type: Article / Article
  • Volume: 34 Issue: 7
  • Publication Date: 2004
  • Doi Number: 10.1023/b:jocc.0000035390.96988.db
  • Title of Journal : JOURNAL OF CHEMICAL CRYSTALLOGRAPHY
  • Page Numbers: pp.477-481

Abstract

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.