DFT study of the thermodynamics of the reactions between 1-O-methyl-2,3-O-isopropylidene-4,6-O-carbonate-α-ᴅ-mannopyranose and methanol or iso-propanol

Data to support article:

Polymers from Sugars and CO₂: Synthesis and Polymerization of a ᴅ-Mannose-Based Cyclic Carbonate

DOI: 10.6084/m9.figshare.3469373

Authors:

Georgina L. Gregory, ^{[a] [b]} Liliana M. Jenisch,^[a] Bethan Charles, ^{[a] [b]} Gabriele Kociok-Köhn^[c] and Antoine Buchard^[a] *

^{[a]    Department of Chemistry, University of Bath, Bath BA2 7AY, UK
[b]    EPSRC Centre for Doctoral Training in Sustainable Chemical Technologies, University of Bath, Bath BA2 7AY, UK
[c]    Chemical Characterisation and Analysis Facility (CCAF), University of Bath, Bath BA2 7AY, UK}

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 1_G (from Mikami et al., J. Am. Chem. Soc. 2013, 135, 6826), by methanol or iso-propanol, to evaluate the regioselectivity of the reactions.

 

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.