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,


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

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

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