The High Performance of Choline Arginate for Biomass Pretreatment Is Due to Remarkably Strong Hydrogen Bonding by the Anion

Amir Karton, Manuel Brunner, Mark J. Howard, Gregory G. Warr, Rob Atkin

Research output: Contribution to journalArticle

10 Citations (Scopus)

Abstract

The ionic liquid choline arginate [Ch][Arg] is more effective for biomass pretreatment than other choline based amino acid ILs, but the underlying mechanism has been unclear. In the present work we use the high-level CCSD(T)/CBS(MP2) and G4(MP2) thermochemical protocols to probe the H-bonding interactions of [Ch][Arg] with water, and organic functional groups commonly found in biomass. We show that the [Ch][Arg] IL forms unusually strong H-bonding interactions with prototypical H-bond donors. For example, we obtain H-bonding interactions of 76.6, 80.0, and 103.6 kJ mol-1 with water, methanol, and phenol, respectively. Our theoretical results shed light on the capacity of [Ch][Arg] to dissolve biomass, and they demonstrate the importance of ion conformation, in addition to speciation, for IL performance more generally. As a point of reference, we compare the H-bonding interactions of [Ch][Arg] with those of a related IL, choline glycinate ([Ch][Gly]), which does not dissolve biomass as effectively as [Ch][Arg].

Original languageEnglish
Pages (from-to)4115-4121
Number of pages7
JournalACS Sustainable Chemistry and Engineering
Volume6
Issue number3
DOIs
Publication statusPublished - 5 Mar 2018

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