Simulation of 13C NMR chemical shifts of carbinol carbon atoms using quantitative structure-spectrum relationships

Abstract

A quantitative structure-spectrum relationship (QSSR) model was developed to simulate 13C nuclear magnetic resonance (NMR) spectra of carbinol carbon atoms for 55 alcohols. The proposed model, using multiple linear regression, contained four descriptors solely extracted from the molecular structure of compounds. The statistical results of the final model show that R2=0.982 4 and S=0.869 8 (where R is the correlation coefficient and S is the standard deviation). To test its predictive ability, the model was further used to predict the 13C NMR spectra of the carbinol carbon atoms of other nine compounds which were not included in the developed model. The average relative errors are 0.94% and 1.70%, respectively, for the training set and the predictive set. The model is statistically significant and shows good stability for data variation as tested by the leave-one-out (LOO) cross-validation. The comparison with other approaches also reveals good performance of this method.