SYNTHESIS AND CONFORMATIONS OF p-(ACETAMIDO)-BUTOXYCALIX[4]ARENE AND p-(BENZAMIDO)-BUTOXYCALIX[4]ARENE

https://doi.org/10.22146/ijc.21693

Firdaus Firdaus(1*), Jumina Jumina(2), Hardjono Sastrohamidjojo(3)

(1) Chemistry Department, Faculty of Mathematics and Natural Sciences Hasanuddin University, Jl. Perintis Kemerdekaan Km 10 Makassar Indonesia 90245
(2) Chemistry Department, Faculty of Mathematics and Natural Sciences, Gadjah Mada University, Yogyakarta Indonesia 55281
(3) Chemistry Department, Faculty of Mathematics and Natural Sciences, Gadjah Mada University, Yogyakarta Indonesia 55281
(*) Corresponding Author

Abstract


The conversion of p-(amino)butoxycalix[4]arene, 1, to p-(acetamido)butoxy-calix[4]arene, 2, and p-(benzamido)butoxycalix[4]arene, 3, via acetylation and benzoylation reactions, respectively have been conducted. The acetylation reactions was conducted by reflux method and room temperature method. The reflux method was conducted by refluxed a solution of 1 and acetic anhydride in acetic acid glacial solvent for 12 hours to result 2 in 53.8% yield; while the room temperature method was conducted by stirred a solution of 1, acetyl chloride, and dry pyridine in dry toluene solvent and inert atmosphere at room temperature for 24 hours to result 2 in 97.8% yield. By the room temperature method and using benzoyl chloride, the compound 3 was obtained in 67.1% yield. Structures of the both compounds were confirmed using IR, 1H NMR, and 13C NMR spectroscopy methods. Pursuant to the 1H-NMR spectral patterns of their bridge methylene and calix aryl protons, they were known that the compound 3 exist in partial cone conformation; whereas the compound 2 exist in partial cone, cone, and 1,2-alternate conformations where the partial cone was the main conformer.


Keywords


p-(amino)butoxycalix[4]arene; p-(acetamido)butoxycalix[4]arene; p-(benzamido)butoxycalix[4]arene

Full Text:

Full Text PDF


References

[1] Arnaud-Neu, F., Collins, E. M., Deasy, M., Ferguson, G., Harris, S. J., Kaitner, B., Lough, A. J., McKervey, M. A., Marques, E., Ruhl, B. L., Schwing-Weill, M. J., and Seward, E. M., 1989, J. Am. Chem. Soc., 111, 8681-8691.

[2] Khan, I. U., Takemura, H., Suenaga, M., Shinmyozu, T., and Inazu, T., 1993, J. Org. Chem., 58, 3158-3161.

[3] Ungaro, R. M., Pochini, A., and Andreetti, G. D., 1984, J. Inclusion Phenom., 2, 199.

[4] Izatt, R. M., Lamb, J. D., Hawkins, R. T., Brown, P. R., Izatt, S. R., and Christensen, J. J., 1983, J. Am. Chem. Soc., 105, 1782-1785.

[5] Loon, J. V., Arduini, A., Coppi, L., Verboom, W., Pochini, A., Ungaro, R., Harkema, S., and Reinhoudt, D. N., 1990, J. Org. Chem., 55, 5639-5649.

[6] Casnati, A., Pochini, A., Ungaro, R., Ugozzoli, F., Arnaud, F., Fanni, S., Schwing, M., Egbering, R. J. M., Jong, F. D., and Reinhoudt, D. N., 1995, J. Am. Chem., Soc., 117, 2767-2777.

[7] Chen, X., Ji, M., Fisher, D. R., and Wai, C. M, 1998, Chem. Commun., 377-378.

[8] Böhmer, V., 1995, Angew. Chem. Int. Ed. Engl., 34, 713-745.

[9] Dung, N. T. K. and Ludwig, R., 1999, New. J. Chem., 23, 603-607.

[10] Israëli, Y. and Detellier, C., 1997, J. Phys. Chem., B, 101, 1897-1901.

[11] Nomura, E., Taniguchi, H., and Tamura, S., 1989, Chemistry Letter, 1125-1126.

[12] Liu, Y., Zhao, B., Zhang, H., Ju. H., Chen, L., and He, X., 2001, Helvetica Chim. Acta., 84, 1969-1975.

[13] Ohto, K., Murakani, E., Shinohara, T., Shiratsuchi, K., Inoue, K., Iwasaki, M., 1997, Anal. Chim. Acta, 341, 275-283.

[14] Scheerder, J., Fochi, M., Engbersen, J. F. J., and Reinhoudt, D. N., 1994, J. Org. Chem., 59, 7815-7820.

[15] Beer, P. D. and Shade, M., 1997, Chem. Commun., 2377-2378.

[16] Nam, K. C., Chun, J. C., Kang, S. O., and Ko, S. W., 1999, Bull. Korean Chem. Soc., 20, 9, 1108-1110.

[17] Yang, Y. S., Ko, S. W., Song, I. H., Ryu, B. J., and Nam, K. C., 2003, Bull. Korean Chem. Soc., 24, 5, 681-683.

[18] Katz, A., Costa, P. D., Lam, A. C. P., and Notestein, J. M., 2002, Chem. Mater., 14, 3364-3368.

[19] Gutsche, C. D., Dhawam, B., Levine, J. A., No. K. H., and Bauer, L. J., 1983, Tetrahedron, 39, 3, 409-426.

[20] Firdaus, Jumina, and Sastrohamidjojo, H., 2007, Indo. J. Chem., 7, 1, 49-57.



DOI: https://doi.org/10.22146/ijc.21693

Article Metrics

Abstract views : 1314 | views : 1082


Copyright (c) 2010 Indonesian Journal of Chemistry

Creative Commons License
This work is licensed under a Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License.

 

Indonesian Journal of Chemistry (ISSN 1411-9420 /e-ISSN 2460-1578) - Chemistry Department, Universitas Gadjah Mada, Indonesia.

Web Analytics View The Statistics of Indones. J. Chem.