The effect of nitrogen atom on double bond pyramidalization

Date

2004-07-01

Author

Ozen, R
Guven, K
Can, H
Balcı, Metin

Metadata

Show full item record

This work is licensed under a Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License.

Item Usage Stats

150
views

0
downloads

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

Suggestions

OpenMETU
Core

The effect of para-cyclophane structure on cyclacenes Türker, Burhan Lemi (2000-02-01) Semiempirical molecular orbital treatment at the level of AMI type has been performed on the Huckel type cyclacenes having the normal and the skew type para-cyclophane moiety embedded into their structures. The cyclophane effect is found to be operative on the lower members by veiling the cryptoannulenic effect which is influential on the heats of formation values and the frontier molecular orbital energies of the higher members as well as the parent cyclacenes.
The effect of boron substitution on cyclacenes Türker, Burhan Lemi; Azizoglu, A (2001-01-15) AM1-type semiempirical molecular orbital treatment was performed on the Huckel-type cyclacenes having certain number of boron atoms at the peri-positions and at the fusion sites of the arenoid rings. The effect of boron atoms is generally destabilizing in all the cases as compared to their unsubstituted cyclacene counterparts. The AM1 results revealed that certain properties of the boron-substituted cyclacenes are affected not only by the number of arenoid rings they have but also by the nature of their per...
The effect of benzo substitution on complexation of diaza 18-crown-6 ethers derivatives with NaClO4 Koylu, MZ; Demirel, N; Polat, FD; Yilmaz, A; Hosgoren, H; Balcı, Metin (Springer Science and Business Media LLC, 2005-06-01) The complexation of the crown ethers with Na+ ion was studied. H-1-NMR chemical shifts are discussed in terms of structural modi. cation as well as also binding studies with UV-vis spectra were included.
The synthesis and sodium-silver ion exchange of sodalites Acar, Aybar Can; Culfaz, A (2003-05-01) Aluminosilicate sodalites of three different types-chlorosodalite, basic sodalite, and oxalate sodalite-have been synthesized in their sodium forms using hydrothermal synthesis. The syntheses were investigated in terms of their relative rates of crystallization and final crystallinities using powder X-ray diffraction. These sodalites were subsequently loaded with silver by aqueous ion exchange. The exchange was studied primarily by monitoring the solution phase. Rate of exchange and equilibrium behavior hav...
THE INFLUENCE OF WATER ON THE ELECTROCHEMICAL POLYMERIZATION OF 3-ACYLPYRROLES VOIGT, M; ROHDE, N; HALLENSLEBEN, ML; Toppare, Levent Kamil (Elsevier BV, 1993-03-22) Several poly(3-acylpyrrole)s have been studied by cyclic voltammetry. The influence of some common impurities like water and cyanide present in the solvent-electrolyte system on the redox behavior of the polymer films were emphasized. Due to the presence of such impurities we have also observed changes in the macroscopic properties of the films such as their electrical conductivities. There is enough evidence that the amount of such impurities can be correlated to the degree of the so called overoxidation p...

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.