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The application of statistical modeling in organic chemistry is emerging as a standard practice for probing structure-activity relationships and as a predictive tool for many optimization objectives. This review is aimed as a tutorial for those entering the area of statistical modeling in chemistry. We provide case studies to highlight the considerations and approaches that can be used to successfully analyze datasets in low data regimes, a common situation encountered given the experimental demands of organic chemistry. Statistical modeling hinges on the data (what is being modeled), descriptors (how data are represented), and algorithms (how data are modeled). Herein, we focus on how various reaction outputs (e.g., yield, rate, selectivity, solubility, stability, and turnover number) and data structures (e.g., binned, heavily skewed, and distributed) influence the choice of algorithm used for constructing predictive and chemically insightful statistical models. 

DFT-level descriptor libraries were constructed to train 2D and 3D graph neural networks for on the-fly the prediction of carboxylic acid and alkyl amine descriptors suitable for statistical modeling of medicinally relevant molecules. 

This Figshare repository contains the datasets and models for our paper titled: Rapid Prediction of Conformationally-Dependent DFT-Level Descriptors using Graph Neural Networks for Carboxylic Acids and Alkyl Amines. It is organized into 2D and 3D, which represent the modeling architectures used in building graph neural networks for molecular descriptors corresponding to acids and amines. Carboxylic acid, primary alkyl amine, and secondary alkyl amine (as well as a combined alkyl amine) libraries are provided in their entirety, including conformer properties. Additional test and external validation statistics for each library are also provided within this repository. 

Organocatalysts impart enantiocontrol over dicoordinated vinyl carbocations in C(sp3) –H functionalization reactions.