芳香醚类化合物13C NMR化学位移模拟

doi:10.11938/cjmr20160302

波谱学杂志 ›› 2016, Vol. 33 ›› Issue (3): 368-377.doi: 10.11938/cjmr20160302

芳香醚类化合物¹³C NMR化学位移模拟

廖立敏^1,2, 黄茜¹, 李建凤^1,2

1. 内江师范学院化学化工学院, 四川内江 641100;
2. 重庆大学化学化工学院, 重庆 400044

收稿日期:2015-09-06 修回日期:2016-07-09 出版日期:2016-09-05 发布日期:2016-09-05
通讯作者: 廖立敏,电话:13990576038,E-mail:liaolimin523@126.com. E-mail:liaolimin523@126.com
基金资助:
Youth Foundation of Education Bureau, Sichuan Province (13ZB0003), Natural Science Foundation of Education Bureau, Sichuan Province (15ZB0272).

Modeling of ¹³C NMR Chemical Shifts in Aromatic Ethers

LIAO Li-min^1,2, HUANG Xi¹, LI Jian-feng^1,2

1. College of Chemistry and Chemical Engineering, Neijiang Normal University, Neijiang 641100, China;
2. College of Chemistry and Chemical Engineering, Chongqing University, Chongqing 400044, China

Received:2015-09-06 Revised:2016-07-09 Online:2016-09-05 Published:2016-09-05
Supported by:
Youth Foundation of Education Bureau, Sichuan Province (13ZB0003), Natural Science Foundation of Education Bureau, Sichuan Province (15ZB0272).

摘要/Abstract

摘要：

构建了基于分子三维结构计算的原子电负性距离矢量（atomic electronegative space distance vector, AESDV），用以描述各芳香醚类化合物分子中不同等价碳原子的化学微环境，并结合原子自身杂化状态指数（AHSI），建立了¹³C核磁共振定量结构波谱关系的多元线性回归模型，复相关系数（R）为0.964，标准误差（SD）为8.673．
经留一法交互检验的复相关系数（R_CV）为0.948，标准误差（SD_CV）为10.362．随机抽出样本进行外部检验，得到测试集的复相关系数（R_test1及R_test2）分别为0.979和0.939，标准误差（SD_test1及SD_test2）分别为6.400和10.162．研究结果表明，使用该方法所建模型具有良好的预测能力和稳定性．

关键词: 原子电负性空间距离矢量(AESDV), ¹³C化学位移, 定量结构波谱关系(QSSR), 芳香醚类化合物

Abstract:

Atomic electronegative space distance vector (AESDV) which characterizing the microenvironment of equivalent carbon atoms was constructed based on the three-dimensional structures of aromatic ethers. The AESDV was then employed in combination with atomic hybridation state index (AHSI) to calculate ¹³C NMR chemical shifts of 46 carbon atoms in 9 aromatic ethers, and to explore quantitative structure spectroscopy relationship. With multiple linear regression (MLR), a model with a correlation coefficient (R) of 0.964 and a standard deviation (SD) of 8.763 was obtained. Cross-validation of the model was performed by leave-one-out procedure (LOO), resulting in a correlation coefficient (R_CV) of 0.948 and a standard deviation (SD_CV) of 10.362. Furthermore, the 9 aromatic ethers were randomly assigned into a training set and a test set, respectively, to validate this model, and the correlation coefficients R_test1 and R_test2 were found to be 0.979 and 0.939, and the standard deviations SD_test1 and SD_test2to be 6.400 and 10.162, respectively. The results showed that the model established can be used to predict ¹³C NMR chemical shifts in aromatic ethers.

Key words: atomic electronegative space distance vector (AESDV), ¹³C chemical shift, quantitative structure spectroscopy relationship (QSSR), aromatic ethers

中图分类号:

O482.53
O641

廖立敏, 黄茜, 李建凤. 芳香醚类化合物¹³C NMR化学位移模拟[J]. 波谱学杂志, 2016, 33(3): 368-377.

LIAO Li-min, HUANG Xi, LI Jian-feng. Modeling of ¹³C NMR Chemical Shifts in Aromatic Ethers[J]. Chinese Journal of Magnetic Resonance, 2016, 33(3): 368-377.

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芳香醚类化合物¹³C NMR化学位移模拟

Modeling of ¹³C NMR Chemical Shifts in Aromatic Ethers

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