Journal
AICHE JOURNAL
Volume 64, Issue 1, Pages 104-122Publisher
WILEY
DOI: 10.1002/aic.15871
Keywords
computer-aided molecular and mixture design; derivative-free optimization; solvent design; reaction rates; solvent-controlled regioselective reactions
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In this article, we investigate reaction solvent design using COSMO-RS thermodynamics in conjunction with computer-aided molecular design (CAMD) techniques. CAMD using COSMO-RS has the distinct advantage of being a method based in quantum chemistry, which allows for the incorporation of quantum-level information about transition states, reactive intermediates, and other important species directly into CAMD problems. This work encompasses three main additions to our previous framework for solvent design (Austin et al., Chem Eng Sci. 2017;159:93-105): (1) altering the group contribution method to estimate hydrogen-bonding and non-hydrogen-bonding sigma-profiles; (2) ab initio modeling of strong solute/solvent interactions such as H-bonding or coordinate bonding; and (3) solving mixture design problems limited to common laboratory and industrial solvents. We apply this methodology to three diverse case studies: accelerating the reaction rate of a Menschutkin reaction, controlling the chemoselectivity of a lithiation reaction, and controlling the chemoselectivity of a nucleophilic aromatic substitution reaction. We report improved solvents/mixtures in all cases. (c) 2017 American Institute of Chemical Engineers AIChE J, 63: 104-122, 2018
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