Title: Guiding Chemical Synthesis: Computational Prediction of the Regioselectivity of CH Functionalization,
Abstract: We will develop a computational method (RegioSQM) for predicting the
regioselectivity of CH functionalization reactions that can be used by
synthetic chemists who are not experts in computational chemistry through a
simple web interface (regiosqm.org). CH functionalization, i.e. replacing the
hydrogen atom in a CH bond with another atom or molecule, is arguably single
most promising technique for increasing the efficiency of chemical synthesis,
but there are no generally applicable predictive tools that predict which CH
bond is most reactive. RegioSQM uses semiempirical quantum chemistry methods to
predict relative stabilities of reaction intermediates which correlates with
reaction rate and our goal is to determine which quantum method and
intermediate give the best result for each reaction type. Finally, we will
experimentally demonstrate how RegioSQM can be used to make the chemical
synthesis part of drug discovery more efficient.