Research Projects: Neural Networks and Machine Learning in Chemistry

Computer-aided Discovery of Novel Chemical Reactions

According to a systematic classification of about 80000 reactions, most organic reactions can be described by a linear (i.e. nucleophilic / electrophilic attack, substitution, elimnination) or cyclic (pericyclic reactions) sequence of electron pushing arrows. However, there is a third class of reactions that we coined "coarctate reations". Coarctate mechanisms include at least one atom (or a sequence of atoms) at which two bonds are made and two bonds are broken simultaneously. A prominent example is the epoxidation of alkenes with peroxocarboxylic acids.

Because of their intricate mechanisms, coarctate reactions are less exhaustively investigated than pericyclic or linear reactions. Based on their common reaction principle, we predicted a number of new reactions which have been realized in the laboratory. Among them are particularly useful synthetic methods such as coarctate cyclizations.

Key Publications:

Reaction planning: computer-aided discovery of a novel elimination reaction.
R. Herges, C. Hoock, Science 1992, 255, 711-713.
DOI

Coarctate transition states: the discovery of a reaction principle.
R. Herges, J. Chem. Inf. Comput. Sci. 1994, 34, 91-102.
DOI

Coarctate and Pseudocoarctate Reactions: Stereochemical Rules
R. Herges, J. Org. Chem. 2015, 80, 11869-11876.
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Two Unusual, Competitive Mechanisms for (2-​Ethynylphenyl)​triazene Cyclization: Pseudocoarctate versus Pericyclic Reactivity
D. Kimball, B. David, R. Herges, M. M. Haley, J. Am. Chem. Soc. 2002, 124, 1572-1573.
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