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A Priori Estimation of Organic Reaction Yields
Author(s) -
Emami Fateme S.,
Vahid Amir,
Wylie Elizabeth K.,
Szymkuć Sara,
Dittwald Piotr,
Molga Karol,
Grzybowski Bartosz A.
Publication year - 2015
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201503890
Subject(s) - a priori and a posteriori , set (abstract data type) , substrate (aquarium) , product (mathematics) , organic solvent , estimation , solvent , biological system , computer science , chain (unit) , mathematics , chemistry , algorithm , thermodynamics , computational chemistry , mathematical optimization , statistical physics , physics , engineering , organic chemistry , philosophy , oceanography , geometry , epistemology , chemical engineering , biology , programming language , geology , astronomy , systems engineering
A thermodynamically guided calculation of free energies of substrate and product molecules allows for the estimation of the yields of organic reactions. The non‐ideality of the system and the solvent effects are taken into account through the activity coefficients calculated at the molecular level by perturbed‐chain statistical associating fluid theory (PC‐SAFT). The model is iteratively trained using a diverse set of reactions with yields that have been reported previously. This trained model can then estimate a priori the yields of reactions not included in the training set with an accuracy of ca. ±15 %. This ability has the potential to translate into significant economic savings through the selection and then execution of only those reactions that can proceed in good yields.