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 1G (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.