Molecular structures of glycal-based bolaamphiphiles: analysis of crystal packing and hydrogen-bond networks

Nathan C. Tice, Sean Parkin, Joseph J. Bozell

Research output: Contribution to journalArticlepeer-review

5 Scopus citations


The crystal structures for the glycal bolaamphiphiles, 1,12-bis-(2,3-α-d-erythro-hex-2-enopyranosyloxy)-dodecane (1) and 1,12-bis-(2,3-α-d-threo-hex-2-enopyranosyloxy)-dodecane (2), were determined by single-crystal X-ray analysis. The structure for 1 showed that the α:α and α:β diastereomers co-crystallized, with occupancy factors determining an isomeric ratio of 69:31. The pyranose rings for both structures are oriented away from each other and adopt a conventional glycal geometry. The head groups are nearly gauche to the hydrophobic chain, which adopts an all-trans zigzag conformation. Bolaamphiphile 1 packs in anti-parallel layers, while bolaamphiphile 2 displays a parallel arrangement of layers. Both structures display a three-dimensional hydrogen-bonding network involving the hydroxylic substituents on the head groups. The high similarity in large-scale solid state structures between 1 and glucosamide bolaamphiphile 3, and 2 and galactosamide bolaamphiphile 4 suggest a strong dependence on head group stereochemistry, and that only a few, key intermolecular interactions between head groups are necessary in controlling the ultimate structure observed. The solid state results may have implications for understanding the intermolecular forces directing nanoscale self-assembly in solution.

Original languageEnglish
Pages (from-to)374-382
Number of pages9
JournalCarbohydrate Research
Issue number2
StatePublished - Feb 4 2008


  • Bolaamphiphile
  • Crystal packing
  • Crystal structure
  • Glucal
  • Hydrogen-bond network
  • Nanoscale materials
  • Self-assembly
  • X-ray
  • galactal

ASJC Scopus subject areas

  • Analytical Chemistry
  • Biochemistry
  • Organic Chemistry


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