The effect of nitrogen atom on double bond pyramidalization

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

JOURNAL OF CHEMICAL CRYSTALLOGRAPHY, vol.34, no.7, pp.477-481, 2004 (SCI-Expanded)

• Publication Type: Article / Article
• Volume: 34 Issue: 7
• Publication Date: 2004
• Doi Number: 10.1023/b:jocc.0000035390.96988.db
• Journal Name: JOURNAL OF CHEMICAL CRYSTALLOGRAPHY
• Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
• Page Numbers: pp.477-481
• Middle East Technical University Affiliated: No

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.