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 polymerisationDOI: 10.6084/m9.figshare.4309616Authors: 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.