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Updated: Oct 8, 2025
Computation of Atmospheric Concentrations of Molecular Clusters from ab initio Thermochemistry
Published on: April 8, 2020
Effects of Configuration and Substitution on C-H Bond Dissociation Enthalpies in Carbohydrate Derivatives: A
Julia A Turner1, Timur Adrianov1, Mia Ahed Zakaria1
1Department of Chemistry, University of Toronto, 80 St. George Street, Toronto, Ontario M5S 3H6 Canada.
Abstract:
Density functional theory was used to calculate C-H bond dissociation enthalpies (BDEs) at each position of a diverse collection of pyranosides and furanosides differing in relative configuration and substitution patterns. A detailed analysis of the resulting data set (186 BDEs, calculated at the M06-2X/def2-TZVP level of theory) highlights the ways in which stereoelectronic effects, conformational properties, and noncovalent interactions can influence the strengths of C-H bonds in carbohydrates. The results point toward opportunities to alter the radical reactivity of carbohydrate derivatives by variation of their stereochemical configuration or the positions and types of protective groups.
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