The effect of nitrogen atom on double bond pyramidalization

Date

2004-07-01

Author

Ozen, R
Guven, K
Can, H
Balcı, Metin

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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.

Subject Keywords

Exocyclic diene, Cycloaddition, Ab initio calculations, Double bond pyramidalization, X-ray analysis

URI

https://hdl.handle.net/11511/57781

Journal

JOURNAL OF CHEMICAL CRYSTALLOGRAPHY

DOI

https://doi.org/10.1023/b:jocc.0000035390.96988.db

Collections

Graduate School of Natural and Applied Sciences, Article

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Citation Formats

R. Ozen, K. Guven, H. Can, and M. Balcı, “The effect of nitrogen atom on double bond pyramidalization,” JOURNAL OF CHEMICAL CRYSTALLOGRAPHY, pp. 477–481, 2004, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/57781.