Coupling and Reactions of Lignols and New Lignin Monomers: A Density Functional Theory Study

Thomas Elder, Jose del Rio, John Ralph, Jorge Rencoret, Hoon Kim, Gregg Beckham, Michael Crowley

Research output: Contribution to journalArticlepeer-review

12 Scopus Citations


This perspective summarizes and compares computational results for the thermodynamics of bond dissociation, coupling, and rearomatization for a number of noncanonical lignin monomer-lignol combinations that have been found to occur experimentally. The noncanonical lignin monomers discussed are tricin, caffeyl alcohol, 5-hydroxyconiferyl alcohol, and piceatannol. Among dimeric combinations, the results for bond dissociation are generally similar, but in cases for which trimers have been reported (tricin-lignol adducts), this value can be quite variable, with stereochemical and structural preferences. Among the adducts examined thus far, the energies associated with quinone methide formation and rearomatization are not dissimilar and would not impede subsequent polymerization. These fundamental studies may help to elucidate how lignin monomers are incorporated into the lignin polymer, provide leads for targeted genetic modification, and be of use in deconstruction for the production of commodity chemicals.

Original languageAmerican English
Pages (from-to)11033-11045
Number of pages13
JournalACS Sustainable Chemistry and Engineering
Issue number30
StatePublished - 3 Aug 2020

Bibliographical note

Publisher Copyright:
© 2020 American Chemical Society.

NREL Publication Number

  • NREL/JA-2800-77352


  • 5-Hydroxyconiferyl alcohol
  • Caffeyl alcohol
  • Lignin
  • Piceatannol
  • Tricin


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