Chinese Journal of Magnetic Resonance >
Modeling of 13C NMR Chemical Shifts in Aromatic Ethers
Received date: 2015-09-06
Revised date: 2016-07-09
Online published: 2016-09-05
Supported by
Youth Foundation of Education Bureau, Sichuan Province (13ZB0003), Natural Science Foundation of Education Bureau, Sichuan Province (15ZB0272).
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 (RCV) of 0.948 and a standard deviation (SDCV) 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 Rtest1 and Rtest2 were found to be 0.979 and 0.939, and the standard deviations SDtest1 and SDtest2 to 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.
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 . DOI: 10.11938/cjmr20160302
[1] Song Ai-hua(宋爱华), Zhang Yan-feng(张延峰), Sha Yi(沙沂), et al. Spectral analysis and structural elucidation of tenofovir disoproxil fumarate (富马酸替诺福韦二吡呋酯波谱数据与结构确证)[J]. Chinese J Magn Reson(波谱学杂志), 2015, 32(3): 542-550.
[2] Wu Chun-li(吴春丽), Li Jie-ming(李杰明), Wei Hui-jie(魏会杰), et al. Spectral analysis and structural elucidation of atorvastatin lactone(阿托伐他汀内酯的波谱学数据与结构确证)[J]. Chinese J Magn Reson(波谱学杂志), 2014, 31(2): 268-277.
[3] Yang Xiao-yan(杨晓艳), Wu Xiang-yu(吴香玉), An Yan-peng(安艳捧), et al. An NMR study on keto-enol tautomerism of indole-3-pyruvic acid(吲哚丙酮酸的酮-烯醇互变异构化的NMR研究)[J]. Chinese J Magn Reson(波谱学杂志), 2014, 31(1): 81-90.
[4] Grant D M, Paul E G. Carbon-13 magnetic resonance II. chemical shift data for the alkanes[J]. J A Chem Soc, 1964, 86: 2 984-2 990.
[5] Lindeman L P, Adams J Q. Carbon-13 nuclear magnetic shifts for the resonance spectrometry. Chemical shifts for the paraffins through C9[J]. Anal Chem, 1971, 43(10): 1 245-1 252.
[6] Tong J, Chen Y, Liu S, et al. Estimation and prediction of 13C NMR chemical shifts of carbon atoms in both alcohols and thiols[J]. J Struct Chem, 2012, 53(6): 1 075-1 080.
[7] Meiler J, Meusinger R, Will M. Fast determination of 13C NMR chemical shifts using artificial neural networks[J]. J Chem Inf Comput Sci, 2000, 40(5): 1 169-1 176.
[8] Tian Fei-fei(田菲菲), Li Zhi-liang(李志良), Wu Shi-rong(吴世容), et al. Calculation of chemical shift in 13C NMR for furanoses(原子电性作用矢量用于呋喃糖核磁共振碳谱化学位移计算)[J]. Chinese J Magn Reson(波谱学杂志), 2006, 23(3): 355-359.
[9] Deng Jie(邓婕), Mei Hu(梅虎), Zhou Peng(周鹏), et al. Modeling quantitative structure-spectrum relationship of 13C NMR chemical shifts of protoberberine alkaloids(原小檗属类生物碱13C核磁共振化学位移的模拟)[J]. Chinese J Magn Reson(波谱学杂志), 2007, 24(2): 211-216.
[10] Yu De-quan(于德泉), Yang Jun-shan(杨峻山). Handbook of Analytical Chemistry (2nd ed): Vol.7(分析化学手册(第二版): 第七分册)[M]. Beijing(北京): Chemical Industry Press(化学工业出版社), 1999. 575.
[11] Aylward G H, Findlay T J. SI Chemical Data (2nd ed) (SI化学数据手册)(第二版)[M]. Beijing(北京): High Education Press(高等教育出版社), 1985. 94.
[12] Zhang Han-qi(张寒琦), Chen Zheng(陈铮), Lin Ying-jie(林英杰), et al. Handbook of Chemical Data(实用化学手册)[M]. Beijing(北京): Science Press(科学出版社), 2001. 682-723.
[13] Zhou Peng(周鹏), Zhou Yuan(周原), Mei Hu(梅虎), et al. Atomic electronegativity interaction vector and atomic hybridation state Index for spectroscopic smiulation of 13C muclear magnetic resonance of Amino acids[J]. Chin J Anal Chem, 2006, 34(2): 200-204.
[14] Li Bo(李波), Zeng Hui(曾晖), Zhou Peng(周鹏), et al. QSAR studies of 7-substituted 20(S)-camptothecin analogues with antitumor activity using three-dmiensional holographic vector of atomic interaction field (3D-HoVAIF) (三维原子场全息作用矢量用于7位取代20(S)-喜树碱衍生物的抗肿瘤活性定量构效关系研究)[J]. Fine Chemicals(精细化工), 2006, 23(1): 41-46.
[15] Golbraikh A, Tropsha A. Beware of q2! [J]. J Mol Graph Model, 2002, 20(4): 269-276.
[16] Sung-sau S, Karplus M. A comparative study of ligand-receptor complex binding affinity prediction methods based on glycogen phosphorylase inhibitors[J]. J Compu Aided Mol Des, 1999, 13(3): 243-258.
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