Synthetic and NMR studies on calix[n]arene (n = 4,6,8) triflates, mesylates, and tosylates

Zsolt Csók, Gábor Szalontai, Gábor Czira, L. Kollár

Research output: Contribution to journalArticle

9 Citations (Scopus)

Abstract

The synthesis and full characterization of eight new calix[n]arene sulfonate esters including their conformational analysis were carried out. While p-tBu-calix[6]arene and p-tBu-calix[8]arene esters are conformationally labile in the temperature interval of 25-100°C, p-tBu-calix[4]arene mono- and diesters were isolated as stable conformers at ambient temperature. Two 1,3-functionalised compounds of these derivatives, p-tert-butylcalix[4]arene ditriflate (5) and dimesylate (6) were shown unexpectedly high conformational stability up to 100°C by dynamic NMR measurements. The NMR measurements confirm the pinched-cone conformation for both derivatives. For the dealkylated calix[4]arene derivatives the partial cone conformer of the triesters have been obtained as major products in all cases.

Original languageEnglish
Pages (from-to)69-77
Number of pages9
JournalSupramolecular Chemistry
Volume10
Issue number1
Publication statusPublished - 1998

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Mesylates
Nuclear magnetic resonance
Derivatives
Cones
Esters
Conformations
Temperature
calix(4)arene

Keywords

  • 'Pinched cone' conformation
  • Calixarene
  • NMR
  • Sulfonate esters

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Synthetic and NMR studies on calix[n]arene (n = 4,6,8) triflates, mesylates, and tosylates. / Csók, Zsolt; Szalontai, Gábor; Czira, Gábor; Kollár, L.

In: Supramolecular Chemistry, Vol. 10, No. 1, 1998, p. 69-77.

Research output: Contribution to journalArticle

Csók, Zsolt ; Szalontai, Gábor ; Czira, Gábor ; Kollár, L. / Synthetic and NMR studies on calix[n]arene (n = 4,6,8) triflates, mesylates, and tosylates. In: Supramolecular Chemistry. 1998 ; Vol. 10, No. 1. pp. 69-77.
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