SYNTHESIS AND CONFORMATIONS OF p-(ACETAMIDO)-BUTOXYCALIX[4]ARENE AND p-(BENZAMIDO)-BUTOXYCALIX[4]ARENE
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
Author: Firdaus, Jumina and
Hardjono Sastrohamidjojo
Journal Code: jpkimiagg070015
