Discovering predictive rules of chemistry from property landscapes

Predicting the chemical and physical properties of molecules often relies on systematic rules relating the properties to molecular characteristics. This Letter introduces a novel method to reveal predictive chemical rules based on analysis of the chemical property landscape, which specifies the functional relationship between a measured property and an appropriate set of molecular variables. As an illustration, we consider landscapes relating the O-17 NMR chemical shift, C-13 NMR chemical shift, and IR vibrational frequency to the moieties attached to a carbonyl group. Implications of this 'Chemscape' formulation for general molecular property prediction are discussed. (C) 2013 Elsevier B.V. All rights reserved.