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 Sharmab and Antoine Bucharda,*

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.