DFT study of the ring-closing reaction by carbonate nucleophilic attack of 3-N-methylthymidine derivatives, displacing a tosyl leaving group

Data to support article:

CO₂-driven stereochemical inversion of sugars to create thymidine-based polycarbonates by ring-opening polymerisation

DOI: 10.6084/m9.figshare.4309616


Authors:

Georgina L. Gregory,^a Elizabeth M. Hierons,^a Gabriele Kociok-Köhn,^a Ram Sharma^b and Antoine Buchard^a,*

^a Department of Chemistry, University of Bath, Bath BA2 7AY

^b Department of Chemical Engineering, University of Bath, Bath BA2 7AY

DFT study:

- DFT optimised geometries and computed free enthalpies of local minima (intermediates) and local maxima (transition states)  were used to investigate the mechanism of ring-closing by intramolecular carbonate nucleophilic attack of 3-N-methylthymidine derivatives, displacing a tosyl leaving group, so as to evaluate the formation of cyclic carbonate monomers trans-1 and cis-1 by this mechanism.

 

Protocol:
rwB97XD/6-31+G(d)/cpcm=acetonitrile/T=298.15K

 

Content:

- Gaussian09 rev D.01 output files

- Ring_Closing_SN2type.pdf, illustrating the calculations made and summarising the enthalpies computed.