Molecular cocrystals of aromatic carboxylic acids with unsymmetrically substituted ureas. The structures of phenylurea and the 1 : 1 adducts of phenylurea with a series of nitro-substituted acids

Australian Journal of Chemistry

Volumn 53, Issue 9, 2000, Pages 767-777

  Bott, Raymond C ^a   Smith, Graham ^a   Wermuth, Urs D ^a   Dwyer, Nathan C ^a  

^a QUEENSLAND UNIVERSITY OF TECHNOLOGY   (Australia)

Author keywords

Adduct; Infrared spectroscopy; Nitrobenzoic acid; Nitrosalicylic acid; Phenylurea; X ray crystal structure

Indexed keywords

EID: 3042671450     PISSN: 00049425     EISSN: None     Source Type: Journal    
DOI: 10.1071/ch00099     Document Type: Article

References (33)

1. Huang, L., Vasanthan, N., and Tonelli, A. E., J. Appl. Polym. Sci., 1997, 64, 281.
2. Scheerder, J., Engbersen, J. F .J., Casnati, A., Ungaro, R., and Reinhoudt, D. N., J. Org. Chem., 1995, 60, 6448.
3. Hollingsworth, M. D., Brown, M. E., Santarsiero, B. D., Huffman, J. C., and Goss, C. R., Chem. Mater, 1994, 6, 1227.
4. Tonelli, A. E., Polym. Int., 1997, 43, 295.
5. Vasanthan, N., Shin, I. D., Huang, L., Nojima, S., and Tonelli, A. E., Macromolecules, 1997, 30, 3014.
6. Videnova-Adrabinska, V., and Etter, M. C., J. Chem. Crystallogr., 1995, 25, 823;
7. Videnova-Abrabinska, V., J. Mater. Chem., 1995, 5, 2307.
8. Smith, G., Baldry, K. E., Kennard, C. H. L., and Byriel, K. A., Aust. J. Chem., 1997, 50, 737.
9. Wentao, Y., Mengkai, L., and Fenquing, M., Mater. Res. Bull., 1996, 31, 1127.
10. Smith, G., Baldry, K. E., Byriel, K. A., and Kennard, C. H. L., Aust. J. Chem., 1997, 50, 727.
11. Harkema, S., and ter Brake, J. H. M., Acta Crystallogr., Sect. B, 1979, 35, 1011;
12. Harkema, S., ter Brake, J. H. M., and Helmholdt, R. B., Acta Crystallogr., Sect. C, 1984, 40, 1733;
13. Harkema, S., Bats, J. W., Weyenberg, A. M., and Feil, D., Acta Crystallogr., Sect. B, 1972, 28, 1646;
14. Harkema, S., ter Brake, J. H. M., van Hummel, G. J., and Helmholdt, R. B., Acta Crystallogr., Sect. C, 1991, 47, 213.
15. Bandoli, G., Clemente, D. A., Brustolon, M., Corjava, C., Pinzano, C., and Colligiani, A., Mol. Phys., 1980, 39, 1145;
16. Wiedenfeld, H., and Knock, F., Acta Crystallogr., Sect. C, 1990, 46, 1038.
17. Smith, G., Kennard, C. H. L., and Byriel, K. A., Aust. J. Chem., 1997, 50, 1021.
18. Itai, A., Yamada, H., Okamoto, T, and Iitaka, Y., Acta Crystallogr., Sect. B, 1977, 33, 1816;
19. Wiedenfeld, H., and Knock, F., Arch. Pharm. (Weinheim, Ger.), 1986, 319, 654.
20. Smith, G., Coyne, M. G., and White, J. M., Aust. J. Chem., 2000, 53, 203.
21. Vogel, A. I., 'Textbook of Practical Organic Chemistry' 5th Edn, p. 964 (Longman Group Ltd: London 1978).
22. teXsan Software Package: Single Crystal Structural Analysis Software, Version 1.6, Molecular Structure Corporation, The Woodlands, TX 77381, U.S.A., 1993.
23. Etter, M. C., Acc. Chem. Res., 1990, 23, 120;
24. Etter, M.C., J. Phys. Chem., 1991, 95, 4601.
25. Etter, M. C., Urbanczyk, Z., Zia-Ebrahimi, M., and Panunto, T. W., J. Am. Chem. Soc., 1990, 112, 8415.
26. Etter, M. C., and Panunto, T. W., J. Am. Chem. Soc., 1988, 110, 5896.
27. Theophanides, T., and Harvey, P. D., Coord. Chem. Rev., 1987, 76, 237.
28. Yamaguchi, A., Miyazawa, T., Shimanouchi, T., and Mizushima, S., Spectrochim. Acta, 1957, 10, 170.
29. Kolodziejski, W., Wawer, I., Wozniak, K., and Klinowski, J., J. Phys. Chem., 1993, 97, 12147.
30. Saito, Y., Machida, K., and Uno, T., Spectrochim. Acta, 1975, 31A, 1237.
31. Mido, Y., Fujita, F., Matsuura, H., and Machida, K., Spectrochim. Acta, 1981, 37A, 103.
32. Bellamy, L. J., 'The Infrared Spectra of Complex Molecules' 3rd Edn (Methuen: London 1958).
33. Mido, Y., and Murata, H., Nippon Kagaku Zasshi, 1969, 90, 254.