Abstract
According to UHF/INDO calculations of the model conformations of the chlorinated nitrobenzene radical anions, the rotation of the nitro group relative to the plane of the benzene ring is accompanied by its pyramidal deformation caused by the pseudo-Jahn–Teller effect. The degree of the structural distortions of the chlorinated nitrobenzene radical anions depends on the arrangement of the chlorine atoms in the benzene ring and on the solvent, increasing from DMF to its mixtures with water. The isotropic hyperfine coupling constants and their dependence on the water content in a binary mixture of solvents are interpreted for a number of chlorinated nitrobenzene radical anions.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
REFERENCES
C. Amatore, C. Combellas, N. Lebbar, et al. J. Org. Chem., 60, 18–26 (1995).
J. F. Bunnett, Tetrahedron, 49, 4477–4484 (1993).
W. Zhao, Y. Liu, and Z. Huang, Synth. Commun., 23, 591–599 (1993).
C. Combellas, H. Marzouk, C. Suba, and A. Thiebault, Synthesis, 8, 788–790 (1993).
R. G. Compton, R. A. W. Dryfe, and A. C. Fisher, J. Chem. Soc., Perkin Trans. 2, 7, 1581–1588 (1994).
V. Arca, C. Paradisi, and C. Scorrano, J. Org. Chem., 55, 3617–3621 (1990).
V. F. Starichenko, Z. A. Shundrin, L. N. Shchegoleva, and V. D. Shteingartz, Zh. Strukt. Khim., 41, No. 3, 457–467 (2000).
I. B. Bersuker and V. Z. Paulinger, Vibronic Interactions in Molecules and Crystals [in Russian], Nauka, Moscow (1983).
P. V. Schastnev and L. N. Shchegoleva, Molecular Distortions in Ionic and Excited States, CRC, New York (1995), p. 82.
F. Ramondo, Can. J. Chem., 70, 314–325 (1992).
V. F. Starichenko, G. A. Selivanova, and V. D. Shteingartz, Zh. Org. Khim., 22, 1255–1263 (1986).
A. Bhar, J. P. Aune, N. Benali-Cherif, et al., Acta Crystallogr., Sect. C, 51, 256 (1995).
N. I. Sedova and L. V. Vilkov, Usp. Khim., 11, 153–184 (1982).
S. Sharma, H. Paulus, N. Weiden, and A. Weiss, Z. Naturforsch. A, 41, 134 (1986).
I. Tanaka, F. Iwasaki, and A. Aihara, Acta Crystallogr., Sect. B, 30, 1546 (1974).
Y. Nakai, Bull. Chem. Soc. Jpn., 39, 1372–1376 (1966).
D. H. Geske, J. L. Ragle, M. A. Bambenek, and A. L. Balch, J. Am. Chem. Soc., 86, 987–1002 (1964).
B. C. Gilbert and M. Trenwith, ibid., 90, 4201–4209 (1968).
J. Spanget-Larsen, Theor. Chim. Acta (Berlin), 51, 65–78 (1979).
T. Fuginaga, Y. Deguchi, and K. Umemoto, Bull. Chem. Soc. Jpn., 46, 2716–2721 (1973).
J. Spanget-Larsen, Mol. Phys., 32, 735–741 (1976).
E. M. Copalakrishna, Z. Kristallogr., 121, 378–384 (1965).
P. Ludwig, T. Layloff, and R. N. Adams, J. Am. Chem. Soc., 86, 4568–4571 (1964).
J. Tino and V. Klimo, Chem. Phys. Lett., 25, 427–429 (1974).
S. Sharma, N. Weiden, and A. Weiss, J. Chem. Phys., 90, 483–491 (1989).
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Starichenko, V.F., Shundrin, L.A., Shchegoleva, L.N. et al. Out-of-Plane Distortions of Chlorinated Nitrobenzene Radical Anions. Journal of Structural Chemistry 41, 778–789 (2000). https://doi.org/10.1023/A:1004854017507
Issue Date:
DOI: https://doi.org/10.1023/A:1004854017507