Isohexide Dinitriles: A Versatile Family of Renewable Platform Chemicals

Jing Wu*, Shanmugam Thiyagarajan, Célia Fonseca Guerra, Pieter Eduard, Martin Lutz, Bart A.J. Noordover, Cor E. Koning, Daan S. van Es

*Corresponding author for this work

Research output: Contribution to journalArticleAcademicpeer-review

5 Citations (Scopus)

Abstract

Building blocks of isohexides extended by one carbon atom at the 2- or 5-positions are now synthetically accessible by a convenient, selective, base-catalyzed epimerization of the corresponding dinitriles. Kinetic experiments using the strong organic base 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) show that all three possible isohexide dinitrile isomers exist within a dynamic equilibrium. An epimerization mechanism based on density functional theory (DFT) calculations is proposed. Structural identification of all three possible isomers is based on NMR analysis and single crystal x-ray crystallography. DFT calculations confirm that the observed crystal structures are indeed the lowest energy conformers of these isohexide derivatives.
Original languageEnglish
Pages (from-to)3202-3211
JournalChemSusChem
Volume10
Issue number16
DOIs
Publication statusPublished - 2017

Keywords

  • Biomass
  • Crystal structures
  • Epimers
  • Isohexides
  • Oxygen heterocycles

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  • Datasets

    CCDC 890377: Experimental Crystal Structure Determination

    Wu, J. (Creator), Thiyagarajan, S. (Creator), Guerra, C. F. (Creator), Eduard, P. (Creator), Lutz, M. (Creator), Noordover, B. A. J. (Creator) & van Es, D. (Creator), Wageningen University & Research, 2017

    Dataset

    CCDC 890378: Experimental Crystal Structure Determination

    Wu, J. (Creator), Thiyagarajan, S. (Creator), Guerra, C. F. (Creator), Eduard, P. (Creator), Lutz, M. (Creator), Noordover, B. A. J. (Creator), Koning, C. E. (Creator) & van Es, D. (Creator), Wageningen University & Research, 2017

    Dataset

    Cite this

    Wu, J., Thiyagarajan, S., Guerra, C. F., Eduard, P., Lutz, M., Noordover, B. A. J., Koning, C. E., & van Es, D. S. (2017). Isohexide Dinitriles: A Versatile Family of Renewable Platform Chemicals. ChemSusChem, 10(16), 3202-3211. https://doi.org/10.1002/cssc.201700617