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

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

DFT study of the thermodynamics of the reaction between dimethyl carbonate and 1-O-methyl-2,3-O-isopropylidene-4,6-O-carbonate-α-ᴅ-mannopyranose 1) Isodesmic reaction modelling Data deposited in figshare repository: DOI: 10.6084/m9.figshare.3469283 2) Transesterification ring-opening modelling Data deposited in figshare repository: DOI: 10.6084/m9.figshare.3469373

Keywords:
DFT,Polymers,ring-opening polymerization,Thermodynamics,regioselectivity,Ring strain

Cite this dataset as:
Buchard, A., Gregory, G., 2016. DFT Modelling of Ring-opening Thermodynamics of mannose-based cyclic carbonate. University of Bath. https://doi.org/10.6084/m9.figshare.3469373.

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Creators

Georgina Gregory
University of Bath

Coverage

Collection date(s):

From 1 January 2016 to 13 July 2016

Documentation

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.

Funders

Whorrod Research Fellowship

Engineering and Physical Sciences Research Council (EPSRC)
https://doi.org/10.13039/501100000266

Doctoral Training Centre in Sustainable Chemical Technologies
EP/G03768X/1

Publication details

Publication date: 21 September 2016
by: University of Bath

Version: 1

DOI: https://doi.org/10.6084/m9.figshare.3469373

URL for this record: https://researchdata.bath.ac.uk/id/eprint/290

Related articles

Gregory, G. L., Jenisch, L. M., Charles, B., Kociok-Köhn, G. and Buchard, A., 2016. Polymers from Sugars and CO2: Synthesis and Polymerization of a d-Mannose-Based Cyclic Carbonate. Macromolecules, 49(19), pp.7165-7169. Available from: https://doi.org/10.1021/acs.macromol.6b01492.

Contact information

Please contact the Research Data Service in the first instance for all matters concerning this item.

Contact person: Antoine Buchard

Departments:

Faculty of Science
Chemistry