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Related Experiment Videos

1lambda(4),4lambda(4),8lambda(4),11lambda(4)-Tetrathiacyclotetradecane-1,4,7,10-tetraylidenetetraaminium

Sophie H Dale1, Mark R J Elsegood, Liam M Gilby

  • 1School of Natural Sciences, University of Newcastle-upon-Tyne, Newcastle-upon-Tyne NE1 7RU, England.

Acta Crystallographica. Section C, Crystal Structure Communications
|June 3, 2005
PubMed
Summary

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Researchers investigated the reactivity of thio-crown [14]aneS(4) with an aminating agent. This reaction led to the crystallization of a novel tetra-aminated tetrathiacyclotetradecane cation with sulfonate anions.

Area of Science:

  • Inorganic Chemistry
  • Crystallography
  • Supramolecular Chemistry

Background:

  • Thio-crown ethers are macrocyclic compounds containing sulfur atoms.
  • Reactions involving thio-crown ethers can lead to novel coordination complexes and supramolecular structures.

Purpose of the Study:

  • To investigate the reactivity of 1,4,8,11-tetrathiacyclotetradecane ([14]aneS(4)) with o-mesitylsulfonylhydroxylamine.
  • To characterize the resulting crystalline product.

Main Methods:

  • Reaction of [14]aneS(4) with o-mesitylsulfonylhydroxylamine.
  • Single-crystal X-ray diffraction analysis to determine the crystal structure.

Main Results:

  • Crystallization of 1lambda(4),4lambda(4),8lambda(4),11lambda(4)-tetrathiacyclotetradecane-1,4,7,10-tetraylidenetetraaminium tetrakis(2,4,6-trimethylbenzenesulfonate).

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  • The compound features a tetra-aminated tetrathiacyclotetradecane cation with NH(2) groups on opposite faces of the macrocycle.
  • The crystal structure exhibits a centrosymmetric space group with hydrogen bonding between the cation and sulfonate anions, forming 2D sheets.

    • Conclusions:

    • The reactivity of [14]aneS(4) with o-mesitylsulfonylhydroxylamine yields a unique tetra-aminated macrocyclic cation.
    • The supramolecular assembly involves hydrogen bonding, leading to a layered structure.