Preparation and X-ray structures of complexes of 18-membered crown ethers with polyfunctional guests: Urea and (O-alkyliso)uronium salts

Jos W.H.M. Uiterwijk, G.J. van Hummel, Sybolt Harkema, Veronika M.L.J. Aarts, Kari Daasvatn, Jan Geevers, H.J. den Hertog, David Reinhoudt

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The preparation and X-ray structure determinations of six complexes of urea and (O-n-butyliso)uronium salts with crown ethers are presented. Urea forms isostructural 5:1 adducts with 18-crown-6 (1) and aza-18-crown-6 (2), in which two urea molecules are each hydrogen bonded to two neighbouring hetero atoms of the macroring. The remaining urea molecules form two-dimensional layers alternating with crown ether layers. In both complexes the macroring has theg+g+a ag−a ag−a g−g−a ag+a ag+a conformation withCi symmetry. In the solid 1:1 complex of O-n-butylisouronium picrate with 18-crown-6 (3) two types of conformations of the macroring were observed: theg+g+a ag−a ag+a ag−g−ag−a ag+a conformation with approximateCm symmetry and to a lesser extent theg+g+a ag−a ag+a g+g+a ag−a ag+a conformation with approximateC2 symmetry. Both conformations allow the guest to form three hydrogen bonds to the macrocyclic host. Three complexes of 18-crown-6 and uronium salts have been prepared and characterized by X-ray crystallography. The 1:1 complexes with uronium nitrate (4) and uronium picrate (5) both exhibit the sameC2 conformation and the same hydrogen bonding scheme as in the least occupied form of the previous complex. A 1:2 complex with uroniump-toluenesulphonate (6) has a different hydrogen bonding scheme (two hydrogen bonds per cation to neighbouring oxygen atoms of the macroring) and a different conformation of the host molecule (theag+a ag−a ag+a ag−a ag+a ag−a conformation with almostD3d symmetry). An attempt to prepare a solid uronium nitrate complex with diaza-18-crown-6 in the same way as the 18-crown-6·uronium nitrate (1:1) complex did not yield the expected result. Instead X-ray analysis revealed that the uronium ion is dissociated, resulting in the nitrate salt of the diprotonated diaza crown ether (7).
Original languageEnglish
Pages (from-to)79-100
JournalJournal of inclusion phenomena
Issue number1
Publication statusPublished - 1988


  • IR-85864
  • urea(-like) guests
  • crystal structures
  • Crown ethers
  • Complexation


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