关键词: 原子电性作用矢量(AEIV), 原子杂化状态指数(AHSI), ¹³C NMR化学位移模拟, 原小檗属类生物碱, 定量构谱关系

Abstract: Atomic electronegativity interaction vector (AEIV) and atomic hybridation state index (AHSI) were employed for quantitative structure spectroscopy relationship modeling of ¹³C NMR chemical shifts of the carbon atoms in protoberberine alkaloids. The five-parameter model yielded r, q, RMSEE and RMSCV of 0.982 9, 0.982 1, 7.732 9 and 7.884 3, respectively. Leave-one-molecule-out (LMO) method and cross test (CT) were combined to test the reliability of this model, and the results appeared satisfactory. Predicted chemical shifts of the samples were in good linear relationship with the experimental data, with r_predof 0.982 9, 0.986 5 and 0.982 1 respectively. The model was also used to predict unknown ¹³C NMR chemical shifts of 58 carbon atoms in four protoberberine compounds, and the results obtained were in agreement with calculated results using the gNMR software.

Key words: atomic electronegativity interaction vector, atomic hybridation state index, NMR, chemical shift, protoberberine alkaloids