Do calix[n]arenes really exist as discrete monomers in solution? Comments based on mass spectrometry

Fumiaki Inokuchi, Seiji Shinkai

Research output: Contribution to journalArticle

12 Citations (Scopus)

Abstract

Mass spectrometric measurements have provided unequivocal evidence that calix[n]arenes (2n), which are so far believed to exist as discrete monomers in solution because of strong intramolecular hydrogen bonding, aggregate partially to form dimers and trimers through intermolecular hydrogen bonds. This trend is particularly conspicuous in 28 and next in 27 and only a very weak dimer peak is observable for 26. In contrast, such an aggregate peak is not detected for 24 and 2 5. The results are consistent with the prediction offered on the basis of theoretical calculations that 24 and 25 can adopt a stable C4- and C5-symmetrical ring structure, respectively, as well as a stable intramolecular hydrogen-bonding array, whereas 26, 27 and 28 feature a pinched ring conformation as their most stable structure which destabilizes the intramolecular hydrogen-bonding array. The new finding reasonably explains several curious aspects of the behaviour of 2n such as very poor solubility of 28 and gelation in organic fluids.

Original languageEnglish
Pages (from-to)601-605
Number of pages5
JournalJournal of the Chemical Society. Perkin Transactions 2
Volume4
Publication statusPublished - Apr 1996
Externally publishedYes

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Calixarenes
Mass spectrometry
Hydrogen bonds
Monomers
Dimers
Gelation
Conformations
Solubility
Fluids

All Science Journal Classification (ASJC) codes

  • Chemistry(all)

Cite this

Do calix[n]arenes really exist as discrete monomers in solution? Comments based on mass spectrometry. / Inokuchi, Fumiaki; Shinkai, Seiji.

In: Journal of the Chemical Society. Perkin Transactions 2, Vol. 4, 04.1996, p. 601-605.

Research output: Contribution to journalArticle

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