Sintesis dan Konformasi p-(Amino)Butoksikaliks[4]Arena
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.
Penulis: Firdaus, Jumina
Jumina, Hardjono Sastrohamidjojo
Kode Jurnal: jpkimiadd070082
