title: Theoretical insight into the pyrolytic deformylation of levoglucosenone and isolevoglucosenone.
abstract: A computational study was conducted to gain insight into the pyrolytic deformylations of levoglucosenone and isolevoglucosenone. Present B3LYP/6-31G(∗) and CBS-QB3 calculations provide valuable evidence to rule out the formation of isolevoglucosenone during the pyrolytic degradation of cellulosic materials. This, along with the supplementary data herein presented and with other recent reports, suggest that levoglucosenone should not be formed directly from levoglucosan (as proposed in numerous reports), but rather from another intermediate, such as 1,4:3,6-dianhydro-α-d-glucopyranose.
authors.affiliation: Instituto de Química de Rosario, Facultad de Ciencias Bioquímicas y Farmacéuticas, Universidad Nacional de Rosario-CONICET, Suipacha 531, S2002LRK Rosario, Argentina. Electronic address: sarotti@iquir-conicet.gov.ar.
authors.forename: Ariel M
authors.initials: AM
authors.lastname: Sarotti
mesh_terms: D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000737:chemistry*; D002236:Carbohydrate Conformation; D003198:Computer Simulation; D005947:Glucose / Q000031:analogs & derivatives* / Q000737:chemistry; D008956:Models, Chemical; D011789:Quantum Theory; D013816:Thermodynamics
chemical_list: C476164:1,6-anhydro-2,3-dideoxyhex-3-enopyran-4-ulose; D019086:Bridged Bicyclo Compounds, Heterocyclic; C512757:1,6-anhydro-3,4-dideoxyhex-3-enopyran-2-ulose; D005947:Glucose
keywords: 3-Oxidopyrylium; DFT; Isolevoglucosenone; Levoglucosenone; Pyrolytic deformylation