Collect. Czech. Chem. Commun.
2001, 66, 947-958
https://doi.org/10.1135/cccc20010947
Self-Assembly of 1,1'-Biphenyl-2,2',6,6'-tetracarboxamides. Effect of Substitution at the Amidic Nitrogen
Petr Holýa, Jaroslav Podlahab, Ivana Císařováb and Jiří Závadaa,*
a Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, 166 10 Prague 6, Czech Republic
b Department of Inorganic Chemistry, Charles University, 128 40 Prague 2, Czech Republic
References
1. Angew. Chem., Int. Ed. Engl. 1999, 38, 381.
< P., Závada J., Císařová I., Podlaha J.: https://doi.org/10.1002/(SICI)1521-3773(19990201)38:3<381::AID-ANIE381>3.0.CO;2-P>
2. According to Eliel3, no organic molecule of D4 symmetry has yet been synthesized. Also, to our best knowledge, no hydrogen bond organized substructure has been found in any known crystal structure.
3. Eliel E. L., Wilen S. H., Mander L. N.: Stereochemistry of Organic Compounds, p. 79. Wiley, New York 1994.
4. Tetrahedron: Asymmetry 1999, 10, 3277.
< M., Kraus T., Závada J., Císařová I., Podlaha J.: https://doi.org/10.1016/S0957-4166(99)00367-5>
5. Z. Kristallogr. 1997, 212, 226.
< P., Císařová I., Podlaha J., Žák Z., Böhm S., Tichý M., Závada J.: https://doi.org/10.1524/zkri.1997.212.3.226>
6. Collect. Czech. Chem. Commun. 2001, 66, 820.
< P., Závada J., Zezula J., Císařová I., Podlaha J.: https://doi.org/10.1135/cccc20010820>
7. J. Chem. Soc. A 1969, 2372.
< L., Schmidt G. M. J.: https://doi.org/10.1039/j19690002372>
8. Acta Crystallogr., Sect. B: Struct. Crystallogr. Cryst. Chem. 1976, 32, 775.
< L.: https://doi.org/10.1107/S0567740876003968>
9. Chem. Mater. 1997, 9, 2983.
< J. F., Murray C. M., Dolan G. M.: https://doi.org/10.1021/cm970350t>
10. Acta Crystallogr., Sect. B: Struct. Crystallogr. Cryst. Chem. 1978, 34, 1230.
< L., Tuval M.: https://doi.org/10.1107/S0567740878005270>
11. Proc. R. Soc. London, Ser. A 1983, 388, 133.
< L., Hagler A. T.: https://doi.org/10.1098/rspa.1983.0076>
12. J. Am. Chem. Soc. 1991, 113, 9265.
< F., Geib S. J., Goswami S., Hamilton A. D.: https://doi.org/10.1021/ja00024a036>
13. Helv. Chim. Acta 1973, 36, 2253.
G., Haas G., Prelog V.:
14. Tetrahedron 1998, 54, 4107.
< K. E., Shipps G. W., Jr., Skyler D. A., Rebek J., Jr.: https://doi.org/10.1016/S0040-4020(98)00139-2>
15. The R absolute configuration of the amide dictates the choice of the space group. The alternative group P6122 involving the opposite helicity of the screw axis would be appropriate for S-isomer.
16. The tetrachloride was crystallized from hot toluene, m.p. 212–214 °C; ref.17 189–190 °C.
17. Chem. Ber. 1911, 44, 2302.
< F.: https://doi.org/10.1002/cber.19110440346>
18. Acta Crystallogr., Sect. A: Fundam. Crystallogr. 1990, 46, 467.
< G. M.: https://doi.org/10.1107/S0108767390000277>
19. Sheldrick G. M.: SHELXL93, Program for Crystal Structure Refinement from Diffraction Data. University of Göttingen, Göttingen 1993.