Abstract
The structure and photochemical properties of 6-methyl-2,4-diphenyl-1-(p-tolyl)pyrimidinium perchlorate (1) and 4,8-dimethyl-2-phenylpyrimido[1,2-f]phenanthridinium (2) formed as a result of photocyclization of1 have been studied. The crystal structure of compound1 has been studied at −140 °C and 25 °C. In cation1, theN-tolyl substituent and α-Ph ring are noncoplanar with the pyrimidinium fragment (the angles are 67.9° and 41.1°, respectively), while the angle between the γ-Ph ring and the pyrimidinium moiety is only 7.1° (−140 °C). The photocyclization product2 has a flattened structure.
Similar content being viewed by others
References
M. I. Knyazhanskii, Y. R. Tymyanskii, V. M. Feigelman, and A. R. Katritsky,Heterocycles, 1987,26, 969.
A. R. Katritskii, B. Agkha, and D. Z. Ville,Khim. Geterotsikl. Soedin., 1984,11, 1509 [Chem. Heterocycl. Compd., 1984,11 (Engl. Transl.)].
A. Camerman, L. H. Jensen, and A. T. Balaban,Acta Crystallogr., 1969,B25, 2623.
S. M. Aldoshin, Ya. R. Tymyanskii, O. A. D'yachenko, L. O. Atovmyan, M. I. Knyazhanskii, and G. N. Dorofeenko,Izv. Akad. Nauk SSSR, Ser. Khim., 1981, 2270 [Bull. Acad. Sci. USSR, Div. Chem. Sci., 1981,30 (Engl. Transl.)].
O. S. Filipenko, S. M. Aldoshin, G. V. Shilov, N. I. Makarova, V. A. Kharlanov, and M. I. Knyazhanskii,Izv. Akad. Nauk SSSR, Ser. Khim., 1995, 296 [Russ. Chem. Bull., 1995,44, 287 (Engl. Transl.)].
V. I. Ponomarev, A. I. Kadykov, and L. O. Atovmyan,Apparatura i metody rentgenovskogo analiza [Apparatus and Methods of X-ray Diffraction Analysis], 1974,15, 14 (in Russian).
G. M. Sheldrick,SHELX-76. Program for Crystal Structure Determination, University of Cambridge, Cambridge (England), 1976.
Author information
Authors and Affiliations
Additional information
Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 9, pp. 1731–1735, September, 1995.
This work was partly (studies performed at Scientific Research Institute of Physical and Organic Chemistry at Rostov State University) supported by the Science Foundation “Russian Universities”.
Rights and permissions
About this article
Cite this article
Makarova, N.I., Knyazhanskii, M.I., Filipenko, O.S. et al. Photochemical properties and the structure of 6-methyl-2,4-diphenyl-1-(p-tolyl)pyrimidinium perchlorate and the product of its photocyclization. Russ Chem Bull 44, 1662–1666 (1995). https://doi.org/10.1007/BF01151287
Received:
Revised:
Issue Date:
DOI: https://doi.org/10.1007/BF01151287