Abstract
The molecular structure of 1,2,4,5-tetracyanobenzene has been determined by gas-phase electron diffraction and by ab initio calculations at several levels of theory. The electron diffraction study indicates an elongation of the aromatic ring along the (H)C•••C(H) axis, characterized by angular deformation of the benzene ring and lengthening of the (NC)C—C(CN) bonds. The following bond lengths (r g) and bond angles were obtained by electron diffraction: \(\left( {C - C} \right)_{ring,mean} 1.406 \pm 0.003{\AA},C - C\left( N \right)1.429 \pm 0.003{\AA},C \equiv N1.161 \pm 0.002{\AA},\angle C_{ipso} - C_{ipso} 118.0 \pm 0.4^ \circ ,C_{ipso} - C_{ipso} C\left( N \right)120.8 \pm 0.3^ \circ \).
Similar content being viewed by others
REFERENCES
Portalone, G.; Domenicano, A.; Schultz, G.; Hargittai, I. J. Mol. Struct. 1987, 160, 97.
Colapietro, M.; Domenicano, A.; Portalone, G.; Schultz, G.; Hargittai, I. J. Mol. Struct. 1984, 112, 141.
Schultz, G.; Brunvoll, J.; Almenningen, A. Acta Chem. Scand. 1986, A40, 77.
Lefebvre, J.; Odou, G.; Muller, M.; Mierzejewski, A.; Luty, T. Acta Cryst. 1989, B45, 323.
Freccero, M.; Fasani, E.; Albini, A. J. Org. Chem. 1993, 58, 1740.
Bailey, A. S.; Henn, B. R.; Langdon, J. M. Tetrahedron 1963, 19, 161.
Hargittai, I.; Tremmel, J.; Kolonits, M. Hung. Sci. Instrum. 1980, 50, 31.
Witt, W. Z. Naturforsch. 1964, A19, 1363.
Colapietro, M.; Domenicano, A.; Portalone, G.; Schultz, G.; Hargittai, I. J. Phys. Chem. 1987, 91, 1728.
Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Gill, P. M. W.; Johnson, B. G.; Robb, M. A.; Cheeseman, J. R.; Keith, T.; Petrsson, G. A.; Montgomery, J. A.; Raghavachari, K.; Al-Laham, M. A.; Zakrzewski, V. G.; Ortiz, J. V.; Foresman, J. B.; Cioslowski, J.; Stefanov, B. B.; Nanayakkara, A.; Challacombe, M.; Peng, C. Y.; Ayala, P. Y.; Chen, W.; Wong, M. W.; Andres, J. L.; Replogle, E. S.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Binkley, J. S.; Defrees, D. J.; Baker, J.; Stewart, J. P.; Head-Cordon, M.; Gonzalez, C.; Pople, J. A. Gaussian 94, Revision B.2, Gaussian, Inc., Pittsburgh, PA, 1995.
Møller, C.; Plesset, M. S. Phys. Rev. 1934, 46, 618.
Hedberg, L.; Mills, I. M. J. Mol. Spect. 1993, 160, 117.
Andersen, B.; Seip, H. M.; Strand, T. G.; Stølevik, R. Acta Chem. Scand. 1969, 23, 3224.
Tavard, C.; Nicolas, D.; Rouault, M. J. Chim. Phys. Phys. Chim. Biol. 1967, 64, 540.
Bonham, R.; Schäfer, L. In International Tables for X-ray Crystallography, vol. 4. Kynoch: Birmingham, 1974, Chap. 2.5, p. 176.
Hargittai, M.; Hargittai, I. J. Chem. Phys. 1973, 59, 2513.
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Schultz, G., Szabados, Á., Tarczay, G. et al. Molecular Structure of 1,2,4,5-Tetracyanobenzene from Gas-Phase Electron Diffraction and Theoretical Calculations. Structural Chemistry 10, 149–155 (1999). https://doi.org/10.1023/A:1022089415252
Issue Date:
DOI: https://doi.org/10.1023/A:1022089415252