¹³C NMR chemical shift prediction of diverse chemical compounds

ABSTRACT

Selection of key descriptors is very important in QSPR analysis. Presence of noise in the subset of descriptors reduces the quality of predictions. A complete set is considered as perfect when it does not include irrelevant or redundant elements. This paper reports complete sets of descriptors used to develop QSPR models for 1786 ¹³C NMR chemical shifts (δ_C parameters) of carbon atoms in 125 diverse chemical compounds. PBE1PBE/6-311G(2d,2p) and B3LYP/6-31G(d) basis sets were used for quantum chemistry calculations after the molecular structures were optimized with semi-empirical AM1 and B3LYP/6-31G(d). The two complete sets consisting of magnetic shielding elements (σ_XX, σ_YY, σ_ZZ) and the chemical shift principal values (σ₁₁, σ₂₂, σ₃₃) were used as the inputs for support vector machine (SVM) models of δ_C parameters. The four SVM models obtained have the mean root mean square (rms) errors of about 4.5–4.6 ppm. The results suggest that SVM models are accurate and acceptable compared with previous models, although our models are based on a relatively large set of compounds. Our approach is valuable in the selection of important descriptors for QSPR studies of δ_C parameters.

KEYWORDS:

• ¹³C NMR chemical shifts
• DFT
• complete set of descriptors
• genetic algorithm
• MLR
• SVM

Acknowledgements

This project was supported by the Scientific Research Fund of Hunan Provincial Education Department (No. 18C0506), Natural Science Foundation of Hunan Province (No. 2019JJ50118).

Disclosure statement

No potential conflict of interest was reported by the authors.