Neural networks for the prediction organic chemistry reactions

Reaction prediction remains one of the great challenges for organic chemistry. Solving this problem computationally requires the programming of a vast amount of knowledge and intuition of the rules of organic chemistry and the development of algorithms for their application. It is desirable to develop algorithms that, like humans, "learn" from being exposed to examples of the application of the rules of organic chemistry. In this work, we introduce a novel algorithm for predicting the products of organic chemistry reactions using machine learning to first identify the reaction type. In particular, we trained deep convolutional neural networks to predict the outcome of reactions based example reactions, using a new reaction fingerprint model. Due to the flexibility of neural networks, the system can attempt to predict reactions outside the domain where it was trained. We test this capability on problems from a popular organic chemistry textbook. ∗To whom correspondence should be addressed †Department of Chemistry and Chemical Biology, Harvard University, Cambridge MA 02138, USA ‡Department of Computer Science, Harvard University, Cambridge MA 02138, USA 1 ar X iv :1 60 8. 06 29 6v 1 [ ph ys ic s. ch em -p h] 2 2 A ug 2 01 6