DFT Modelling of Ring-opening Thermodynamics of mannose-based cyclic carbonate

Data collection method:

DFT study: - DFT optimized geometries and computed free enthalpies were used to calculate the thermodynamics of the ring-opening of D-mannose based monomer 1 (1-O-methyl-2,3-O-isopropylidene-4,6-O-carbonate-α-ᴅ-mannopyranose) or D-glucose counterpart monomer 1G (from Mikami et al., J. Am. Chem. Soc. 2013, 135, 6826), by methanol or iso-propanol, to evaluate the regioselectivity of the reactions. DFT study: - DFT optimized geometries and computed enthalpies were used to calculate the thermodynamics of the isodesmic reactions between dimethyl carbonate and D-mannose based monomer 1 (1-O-methyl-2,3-O-isopropylidene-4,6-O-carbonate-α-ᴅ-mannopyranose) or D-glucose counterpart monomer 1G (from Mikami et al., J. Am. Chem. Soc. 2013, 135, 6826), so as to evaluate the ring-strains of the 2 monomers. Protocols: rwB97XD/6-311++G(2d,p)/cpcm=dichloromethane/T=298.15K rM06-2X-D3/6-311++G(2d,p)/cpcm=dichloromethane/T=298.15K Content: - Gaussian09 rev D.01 output files - Thermodynamics and regioselectivity of ring-opening.pdf, illustrating the calculations made and summarizing the free enthalpies computed. - Ring_Strain_Evaluation.pdf, illustrating the calculations made and summarizing the enthalpies computed.