Indonesian Journal of Chemistry
Vol 7, No 2 (2007)

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

Firdaus Firdaus (Chemistry Department, Faculty of Mathematics and Natural Sciences Hasanuddin University, Jl. Perintis Kemerdekaan Km 10 Makassar Indonesia 90245)
Jumina Jumina (Chemistry Department, Faculty of Mathematics and Natural Sciences, Gadjah Mada University, Yogyakarta Indonesia 55281)
Hardjono Sastrohamidjojo (Chemistry Department, Faculty of Mathematics and Natural Sciences, Gadjah Mada University, Yogyakarta Indonesia 55281)



Article Info

Publish Date
20 Jun 2010

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.

Copyrights © 2007






Journal Info

Abbrev

ijc

Publisher

Subject

Chemical Engineering, Chemistry & Bioengineering Chemistry

Description

Indonesian Journal of Chemistry is an International, peer-reviewed, open access journal that publishes original research articles, review articles, as well as short communication in all areas of chemistry including applied chemistry. The journal is accredited by The Ministry of Research, Technology ...