SYNTHESIS AND CONFORMATION OF p-(AMINO)BUTOXYCALIX[4]ARENE

https://doi.org/10.22146/ijc.21712

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

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

Abstract


Derivatization of 5,11,17,23-tetra-t-butyl-25,26,27,28-tetrahydroxycalix[4]-arene to 5,11,17,23-tetra-amino-25,26,27,28-tetrabutoxycalix[4]arene compound via etherification, ipso nitration, and reduction reactions, respectively has been conducted. The etherification reaction was carried out by refluxed the mixture of 5,11,17,23-tetra-t-butyl-25,26,27,28-tetrahydroxy-calix[4]arene, 1-bromobutane, NaI, and NaH in solvent mixture of THF-DMF (10:1 v/v) and nitrogen atmosphere for 4 hours to resulted 5,11,17,23-tetra-t-butyl-25,26,27,28-tetrabutoxycalix[4]-arene 84% in yield; ipso nitration reaction was carried out by stirred the mixture of 5,11,17,23-tetra-t-butyl-25,26,27,28-tetrabutoxycalix[4]arene and HNO3 100% in solvent mixture of dichloromethane-acetic acid glacial (1:1 v/v) for 2 hours and than refluxed for 1 hour to resulted 5,11,17,23-tetra-nitro-25,26,27,28-tetra-butoxycalix[4]arene 50% in yield; and reduction reaction was carried out by refluxed the mixture of 5,11,17,23-tetra-nitro-25,26,27,28-tetrabutoxycalix[4]arene and SnCl2/HCl reductor in ethanol solvent for 6 hours to resulted 5,11,17,23-tetra-amino-25,26,27,28-tetrabutoxycalix[4]arene 67% in yield. In the etherification reaction, the conformation of calix[4]arene compound was converted from cone to partial cone; but in the followed reactions, i.e. nitration and reduction reactions, the conformation of calix[4]arene compounds were remain in partial cone.


Keywords


aminobutoxycalixarene; conformation; etherification; ipso nitration; reduction

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DOI: https://doi.org/10.22146/ijc.21712

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