NMR and Crystallographic Studies of a p-Sulfonatocalix[4] arene-Guest Complex

Seiji Shinkai, Koji Araki, Tsutomu Matsuda, Nobuaki Nishiyama, Hirotaka Ikeda, Isao Takasu, Masakazu Iwamoto

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Abstract

The 1H and 13C NMR spectra of a complex formed from tetrasodium p-sulfonatocalix[4]arene (I4) and trimelhylanilinium chloride (2) in D2O showed that 2 is bound to the cavity of cone-shaped I4: in the acidic pH region (pD 0.4) the phenyl moiety resides in the cavity, whereas in the neutral pH region (pD 7.3) both the trimethylammonium and the phenyl moiety are included nonspecifically in the cavity. The difference was accounted for by the change in the electron density in the benzene π-systems induced by the dissociation of OH groups. The complex was crystallized from acidic aqueous solution. The solid-state 13C NMR (CP-MAS) supports the inclusion of the phenyl moiety in the cavity. The X-ray crystallographic studies established that (i) 14 adopts a cone conformation, (ii) I4 and 2 form a host-guest-type complex with the phenyl moiety inserted into the cavity, (iii) not only the hydrophobic force but also the electrostatic force operates for guest inclusion, and (iv) the overall structure is similar to that of clays, I4 molecules being arranged into bilayers. These findings serve as a useful cross-link between solution complexes and solid-state complexes.

Original languageEnglish
Pages (from-to)9053-9058
Number of pages6
JournalJournal of the American Chemical Society
Volume112
Issue number25
DOIs
Publication statusPublished - Jan 1990

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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    Shinkai, S., Araki, K., Matsuda, T., Nishiyama, N., Ikeda, H., Takasu, I., & Iwamoto, M. (1990). NMR and Crystallographic Studies of a p-Sulfonatocalix[4] arene-Guest Complex. Journal of the American Chemical Society, 112(25), 9053-9058. https://doi.org/10.1021/ja00181a004