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Parameterization of the ReaxFF reactive force field for a proline‐catalyzed aldol reaction
Author(s) -
Hubin Pierre O.,
Jacquemin Denis,
Leherte Laurence,
Vercauteren Daniel P.
Publication year - 2016
Publication title -
journal of computational chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.907
H-Index - 188
eISSN - 1096-987X
pISSN - 0192-8651
DOI - 10.1002/jcc.24481
Subject(s) - reaxff , aldol reaction , transferability , molecular dynamics , chemistry , force field (fiction) , catalysis , reactive intermediate , computational chemistry , reaction intermediate , organocatalysis , organic chemistry , computer science , enantioselective synthesis , interatomic potential , logit , machine learning , artificial intelligence
A parameterization of the ReaxFF reactive FF is performed using a Monte Carlo Simulated Annealing procedure for the modeling of a proline‐catalyzed aldol reaction. Emphasis is put on the accurate reproduction of the relative stabilities of several key intermediates of the reaction, as well as, on the description of the reaction path bridging these intermediates based on quantum mechanical calculations. Our training sets include new criteria based on geometry optimizations and short Molecular Dynamics simulations to ensure that the trained ReaxFF potentials adequately predict the structures of all key intermediates. The transferability of the sets of parameters obtained is assessed for various steps of the considered aldol reaction, as well as for different substrates, catalysts, and reagents. This works indeed highlights the challenge of reaching transferable parameters for several reaction steps. © 2016 Wiley Periodicals, Inc.