DFT study of the ring opening of cyclohexene oxide by an aminophosphonium salt

Data to support article:
Aminophosphonium organocatalysts for the ring-opening copolymerisation of epoxide and cyclic anhydride

Journal: Chemical Communications

Authors: Ella F Clarka, Estelle Dunstan,a Gabriele Kociok-Köhnb and Antoine Buchardc
a Department of Chemistry, University of Bath, Bath, BA2 7AY, UK.
b Materials and Chemical Characterisation Facility, University of Bath, UK
c Department of Chemistry, University of York, York, YO10 5DD, UK.
E-mail : [e-mail]

Description:
DFT optimised geometries and computed free enthalpies of local minima (intermediates) and local maxima (transition states) were used to investigate the mechanism of the reaction between a molecule of cyclohexene oxide and an aminophosphonium bromide salt, to account for the epoxide ring opening initiation step of the ROCOP process.

Protocols:
Gaussian16 (rev C.01) software
Functional: rwB97XD; Solvent model: cpcm=(tetrahydrofuran)
Basis sets:
C H: 6-31+g(d,p)
N P O Br: 6-311+g(d)

Free enthalpies were recomputed using Grimme quasi-harmonic approximation of Grimme, with a cut off frequency of 100 cm–1, and a temperature and concentration correction (T=393.15 K, [CHO]=5.07 mol/L and [catalytic species]=0.0127 mol/L ).

Content:
- Gaussian16 rev C.01 output files
- CHO ring opening.pdf, illustrating the calculations made and summarising the free enthalpies computed