Solvent Effects on the
9-Hydroxymethylanthracene +
<i>N</i>-Ethylmaleimide Diels−Alder Reaction.
A Theoretical Study
José I. García
José A. Mayoral
Luis Salvatella
10.1021/jo048257t.s001
https://acs.figshare.com/articles/journal_contribution/Solvent_Effects_on_the_9_Hydroxymethylanthracene_i_N_i_Ethylmaleimide_Diels_Alder_Reaction_A_Theoretical_Study/3300442
The origin of the high reaction rates of the 9-hydroxymethylanthracene + <i>N</i>-ethylmaleimide Diels−Alder reaction in
fluorous solvents and supercritical carbon dioxide is analyzed through a combination of regression analyses and
theoretical calculations. Both approaches allow the solvent
effects on the activation barrier (a decrease by solvophobic
interactions, an increase by dipolarity−polarizability) to be
attributed to the existence of a hydrogen bond between the
two reactants in the transition state, refuting a previous
hypothesis based on strong solvophobic interactions.
2005-02-18 00:00:00
origin
reactants
Hydroxymethylanthracene
calculation
fluorou
solvophobic interactions
solvent
Theoretical
Ethylmaleimide
hydroxymethylanthracene
barrier
dipolarity
regression
Diel
dioxide
activation
ethylmaleimide
combination
refuting
Solvent
analyses
approach
transition
hypothesis
bond