Abstract
Charges on carbon atoms in the molecules of 4-aryl-substituted [2.2]paracyclophanes were estimated and the role of charge control as a kinetic factor in regioselectivity of their complexation with (NH3)3Cr(CO)3 was investigated using electron density distribution analysis by the Bader, Weinhold-Reed (NPA), and Mulliken methods. The most plausible picture of the electron density distribution in substituted [2.2]paracyclophanes was obtained by the Bader method and compared with experimental data on the yields of reaction products. Topological analysis of the electron density distribution in the [2.2]paracyclophane molecule by the Bader method confirmed the existence of a weak antibonding interaction between the stacked benzene rings.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
E. V. Sergeeva, V. I. Rozenberg, E. V. Vorontsov, T. V. Mikul'shina, N. V. Vorontsova, A. V. Smirnov F. M. Dolgushin, and A. I. Yanovsky.Izv. Akad. Nauk, Ser. Khim., 1998, 142 [Russ. Chem. Bull., 1998,47, 144 (Engl. Transl.)].
G. A. Papoyan, K. P. Butin, R. Hoffmann, and V. I. Rozenberg,Izv. Akad. Nauk, Ser. Khim., 1998, 151 [Russ. Chem. Bull., 1998,47, 153 (Engl. Transl.)].
P. J. Dyson, D. G. Humphrey, J. E. McGrady, D. M. P. Mingos, and D. J. Wilson,J. Chem. Soc., Dalton Trans., 1995, 4039.
M. J. Frish, G. W. Trucks, H. B. Shlegel, P. M. Gill, B. G. Johnson, M. A. Robb, J. R. Cheeseman, T. Keith, G. A. Petersson, J. A. Motgomery, K. Raghavachari, M. A. Al-Laham, V. G. Zakrzewski, A. Nanayakkara, M. Challacombe, C. Y. Peng, P. Y. Ayala, W. Chen, M. W. Wong, J. L. Andres, E. S. Repogle, R. Gomperts, R. L. Martin, D. J. Fox, J. S. Binkley, D. J. DeFrees, L. Baker, J. P. Stewart, M. Head-Gordon, M. C. Gonzales, and J. A. Pople,Gaussian Program. Version Gaussian 94, Rev. El, Gaussian, Inc., Pittsburgh (PA) 1995.
F. W. Biegler-Kunig, R. F. W. Bader and T.-H. Tang,J. Comput. Chem., 1982,3, 317.
R. S. Mulliken,J. Chem. Phys., 1955,23, 1833.
A. E. Reed, I. A. Curtiss and F. Weinhold,Chem. Rev., 1988,88, 899.
R. F. W. Bader,Atoms in Molecules. A Quantum Theory, Clarendon Press, Oxford 1994, 438 pp.
W. J. Hehre, L. Radom, P. v. R. Schleyer and J. A. Pople,Ab initio Molecular Orbital Theory, Wiley, New York, 1986, 548 pp.
I. Lee,Adv. Phys. Org. Chem., 1992,27, 57.
J. Cioslowski,J. Am. Chem. Soc., 1989,111, 8333.
K. B. Wiberg and C. M. Breneman,J. Am. Chem. Soc., 1990,112, 8765.
K. B. Wiberg and P. R. Rablen,J. Comput. Chem., 1993,14, 1504.
B. S. Stefanov and J. Cioslowski,J. Comput. Chem., 1995,16, 1394.
T. S. Slee,J. Am. Chem. Soc., 1986,108, 7541.
P. I. Dem'yanov, E. M. Myshakin, D. P. Krut'ko, and V. S. Petrosyan,Izv. Akad. Nauk, Ser. Khim., 1997, 2111 [Russ. Chem. Bull., 1997,46, 1996 (Engl. Transl.)].
P. I. Dem'yanov, E. M. Myshakin, and V. S. Petrosyan,Izv. Akad. Nauk, Ser. Khim., 1998, 608 [Russ. Chem. Bull., 1998,47, 587 (Engl. Transl.)].
Author information
Authors and Affiliations
Additional information
Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 3, pp. 441–444, March, 1999.
Rights and permissions
About this article
Cite this article
Myshakin, E.M., Butin, K.P. Electron density distribution in molecules of 4-aryl-substituted [2.2]paracyclophanes and regioselectivity of their complexation with Cr(CO)3 . Russ Chem Bull 48, 438–441 (1999). https://doi.org/10.1007/BF02496157
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF02496157