title: Intelligent Approach to Solvent Substitution: The Identification of a New Class of Levoglucosenone Derivatives.
abstract: With the increasing restriction and control of hazardous solvents, safer alternatives need to be identified. Here a contemporary approach to solvent selection and substitution is presented that offers a more scientific alternative to the simple "like-for-like" exchange. A new family of levoglucosenonederived compounds is proposed, modeled to determine their solvent properties, synthesized, and tested. These new molecules show promise as replacements for polar aprotic solvents that have chronic toxicity issues, such as dichloromethane, nitrobenzene, and N-methylpyrrolidinone. The success of this approach makes it possible for academia and industry to make calculated, intelligent choices for solvent substitution in the future.
authors.affiliation: Department of Chemistry, University of York, Heslington, York, YO10 5DD, UK.
authors.forename: Ana
authors.initials: A
authors.lastname: Alves Costa Pacheco
authors.affiliation: Department of Chemistry, University of York, Heslington, York, YO10 5DD, UK.
authors.forename: James
authors.initials: J
authors.lastname: Sherwood
authors.affiliation: Department of Chemistry, University of York, Heslington, York, YO10 5DD, UK.
authors.forename: Anna
authors.initials: A
authors.lastname: Zhenova
authors.affiliation: Department of Chemistry, University of York, Heslington, York, YO10 5DD, UK.
authors.forename: Con R
authors.initials: CR
authors.lastname: McElroy
authors.affiliation: Department of Chemistry, University of York, Heslington, York, YO10 5DD, UK.
authors.forename: Andrew J
authors.initials: AJ
authors.lastname: Hunt
authors.affiliation: Department of Chemistry, University of York, Heslington, York, YO10 5DD, UK.
authors.forename: Helen L
authors.initials: HL
authors.lastname: Parker
authors.affiliation: Department of Chemistry, University of York, Heslington, York, YO10 5DD, UK.
authors.forename: Thomas J
authors.initials: TJ
authors.lastname: Farmer
authors.affiliation: Department of Chemistry, University of York, Heslington, York, YO10 5DD, UK.
authors.forename: Andri
authors.initials: A
authors.lastname: Constantinou
authors.affiliation: Department of Chemistry, University of York, Heslington, York, YO10 5DD, UK.
authors.forename: Mario
authors.initials: M
authors.lastname: De Bruyn
authors.affiliation: Department of Chemistry, University of York, Heslington, York, YO10 5DD, UK.
authors.forename: Adrian C
authors.initials: AC
authors.lastname: Whitwood
authors.affiliation: Circa Group Pty Ltd, 551 Burwood Highway, Knoxfield, Victoria, 3180, Australia.
authors.forename: Warwick
authors.initials: W
authors.lastname: Raverty
authors.affiliation: Department of Chemistry, University of York, Heslington, York, YO10 5DD, UK.
authors.forename: James H
authors.initials: JH
authors.lastname: Clark
mesh_terms: D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000737:chemistry*; D003362:Cost-Benefit Analysis; D005947:Glucose / Q000031:analogs & derivatives* / Q000737:chemistry; D055772:Green Chemistry Technology / Q000191:economics; D012997:Solvents / Q000737:chemistry*
chemical_list: D019086:Bridged Bicyclo Compounds, Heterocyclic; D012997:Solvents; C512757:1,6-anhydro-3,4-dideoxyhex-3-enopyran-2-ulose; D005947:Glucose
keywords: biomass; green chemistry; molecular modeling; solvatochromism; solvent effects