Inclusion behavior of water-soluble thiacalix- and calix[4]arenes towards substituted benzenes in aqueous solution

Literature Information

Publication Date 2003-01-28
DOI 10.1039/B210198J
Impact Factor 3.876
Authors

Noriyoshi Kon, Nobuhiko Iki, Sotaro Miyano


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Abstract

Inclusion abilities of thiacalix- and calix[4]arenetetrasulfonate (3 and 4) towards mono-substituted benzenes were investigated in neutral aqueous solution. In general, the hosts regioselectively encapsulated the guests from the aromatic moiety except the complexation of toluene by 4, in which the guest penetrated from either the aromatic or the methyl group. Stabilities of the inclusion complexes increased with the electron-withdrawing ability of the substituent on the guest, suggesting π–π electronic interaction between the host and guest. In spite of the lower electron density of the aromatic ring, thiacalix[4]arene 3 showed higher inclusion ability than calix[4]arene 4, suggesting that the size rather than the electron density of the calix framework is a more important factor in determining the inclusion ability.

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Organic & Biomolecular Chemistry

Organic & Biomolecular Chemistry
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