羰基化合物分子距边矢量与其13C NMR δC的关系

摘要/Abstract

摘要：

通过对155个羰基化合物中羰基碳原子的¹³C NMR谱与其分子距离-边数矢量(MDE)、立体效应参数(γ 效应)关系的研究，发现羰基化合物羰基碳的¹³C NMR谱化学位移可表示为：

δ_C=a+bμ₅₁+cμ₅₂+dμ₅₃+eμ₅₄+fγ

此式不仅在一定程度上表明了羰基化合物¹³C NMR谱化学位移与其分子结构信息之间的关系，同时也提供了一种计算羰基化合物¹³C NMR化学位移的新方法，并对解析和预测其¹³C NMR谱提供了理论依据. 

关键词: ¹³C NMR, 羰基化合物, 化学位移, 分子距离-边数矢量, γ效应

Abstract:

Carbon-13 chemical shifts of 155 carbonyl groups were measured from 155 carbonyl compounds. The relationships between the ¹³C chemical shifts and the molecular distance-edge vector (MDE) and the γ parameter of the compounds were studied. The results indicated that the ¹³C chemical shifts of carbonyl compounds could be calculated by following equation:

δ_C=a+bμ₅₁+cμ₅₂+dμ₅₃+eμ₅₄+fγ.

Key words: ¹³C NMR carbonyl compound, chemical shift, molecular distance-edge vector, γ parameter

中图分类号:

O482.53

仝建波, 李美萍, 张生万, 李小燕, 杜军栋. 羰基化合物分子距边矢量与其¹³C NMR δ_C的关系[J]. 波谱学杂志, 2006, 23(1): 71-80.

TONG Jian-Bo, LI Mei-Ping, ZHANG Sheng-Wan, LI Xiao-Yan, DU Jun-Dong. Relationship between Molecular Distance-Edge Vector and ¹³C Chemical Shifts of Carbonyl Compounds[J]. Chinese Journal of Magnetic Resonance, 2006, 23(1): 71-80.

参考文献

[1] Ning Yong-cheng(宁永成). Structure Identifying of Organic Compound and Organic Spectroscopy(有机化合物结构鉴定与有机波谱学)
[M]. Beijing(北京)： Science Press(科学出版社), 2000. 1-2.

[2] 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: 1 169-1 176.

[3] Jaramillo J C P, Velazco D R M, Baldrich C. Semiquantitative Analysis of Thiophenic Compounds in Light Cycle Oil (LCO) Using ¹³C NMR Spectroscopy[J]. Fuel, 2004, 83: 337-342.

[4] Rufino A R, Brant A J C, Santos J B O, et al. Simple Method for Identification of Skeletons of Aporphine Alkaloids from ¹³C NMR Data Using Artificial Neural Networks[J]. J Chem Inf Model, 2005, 453(3): 645-651.

[5] Tenailleau E J, Lancelin P, Robins R J, et al. Authentication of the Origin of Vanillin Using Quantitative Natural Abundance ¹³C NMR
[J]. J Agric Food Chem, 2004, 52: 7 782-7 787.

[6] Benzi C, Cossi M, Barone V, et al. A Combined Theoretical and Experimental Approach to Determing Order Parameters of Solutes in Liquid Crystals from ¹³C NMR Data[J]. J Phys Chem B, 2005, 109: 2 584-2 590.

[7] Witkowski S, Maciejewska D, Wawer I. ¹³C NMR Studies of Conformational Dynamics in 2,2,5,7,8 -pentameth-ylchroman-6-ol Derivatives in Solution and the Solid State[J]. J Chem Soc Perkin Trans 2, 2000, 1 471-1 476.

[8] Neuvonen H, Neuvonen K. Correlation Analysis of Carbonyl Carbon ¹³C NMR Chemical Shifts, IR Absorption Frequencies and Rate Coefficients of Nucleophilic Acyl Substitutions. A Novel Explanation for the Substituent Dependence or Reactivity[J]. J Chem Soc Perkin Trans 2, 1999, 1 497-1 502.

[9] Grant D M, Paul E G. Carbon-13 Magnatic Resonance Ⅱ Chemical Shift Data for the Alkanes[J]. J Am Chem Soc, 1964, 86: 2 984-2 990

[10] Lindeman L P, Adams J Q. Carbon-13 Nuclear Magnatic Resonance Spectrometry. Chemical Shifts for the Paraffins through C9[J]. Anal Chem, 1971, 43(10): 1 245-1 252.

[11] Panaye A, Doucet J P, Fan B T. Topological Approach of ¹³C NMR Spectral Simulation: Application to Fuzzy Substructures[J]. J Chem Inf Comput Sci, 1993, 33: 258-265.

[12] HU C Y, Xu L. A New Topological Index for the Changchun Institute of Applied Chemistry ¹³C NMR Information System[J]. Anal Chim Acta, 1995, 318: 117-123.

[13] Liu Shu-shen(刘树深), YU Ban-mei(余般梅), Cao Chen-zhong(曹晨忠), et al. On Carbon-13 Nuclear Magnetic Resonance Spectrometry: Approach to Chemical Shift in Alkane Molecules with a Novel Atomic Distance-Edge(ADE, μ)Vector(核磁共振碳谱的研究：烷烃分子的化学位移δ与原子距边矢量μ)[J]. Chinese Journal of Atomic and Molecular Physics(原子与分子物理学报), 1997，14（4）：606-614.

[14] Cao Chen-zhong(曹晨忠), Liu Chao(刘超), Liu Shu-shen(刘树深), et al. Carbon Atom Distance-Edge Vector and ¹³C NMR Chemical Shifts of Alkanes(原子距边矢量、三键数与烷烃的¹³C NMR化学位移)[J]. Chinese J Magn Reson(波谱学杂志)，1998, 15(4): 347-353.

[15] Liu Shu-shen(刘树深), Xia Zhi-ning(夏之宁),Yu Ban-mei(余般梅), et al. Atomic Electronegative Distance Vector of Acyclic Alcohol and Chemical Shift Simulation of ¹³C NMR Spectroscopy(无环醇原子电距矢量及核磁共振碳谱化学位移模拟)[J]. Chinese J Magn Reson(波谱学杂志), 1999, 16(5): 429-440. 

[16] Khadikar P V, Pathre S V, Shrivastava A. Structural Assignment of 2,6- and 2,7-Disubstituted Naphthalenes and Prediction of ¹³C Nuclear Magnetic Resonance Chemical Shifts: Applications of Topology and Two-Dimensional NMR Spectroscopy[J]. Bioorg Med Chem Lett, 2002, 12: 2 673-2 680.

[17] Li Mei-ping(李美萍)，Lu Fei(芦飞)，Tong Jian-bo(仝建波)，et al. Study on the Structure Parameters of Carbonyl Compound and the ¹³C NMR Chemical Shift(羰基化合物结构参数与其¹³C NMR谱化学位移的关系)[J]. Chemistry(化学通报), 2004, 10: 778-782.

[18] Lin Zhi-hua(林治华), Xu Jiang-he(胥江河), Liu Shu-shen(刘树深), et al. Study on Quantitative Structure-Property Relationship of Chain Hydrocarbons, Aldehydes and Alkanones by Molecular Distance-Edge Vector(分子距边矢量研究链烃与醛酮的定量构效关系)[J]. Acta Phys Chem Sin(物理化学学报), 2000,16(2): 153-161.

[19] Sadtler Standard Carbon-13 NMR Spectra[M]. Sadtler Research Laboratories Division of Bio-Rad Laboratories, INC. Printed in the United States of America, 1980.1-8 000.

[20] http://www.aist.go.jp/RIODB/SDBS/cgi bin/cre_index.cgi.

[21] Nie Jin-yuan(聂金媛)，Liao Chun-yang(廖春阳)，Wu Shi-rong(吴世容)，et al. Estimation and Prediction of Gas Chromatography Retention Time of Components Separated from Symplocos Sumunlia through MEDV(分子电距矢量对山矾花中头香成分气相色谱保留时间的估计和预测)[J]. Fine Chemicals(精细化工), 2004, 21(4): 273-278.

羰基化合物分子距边矢量与其¹³C NMR δ_C的关系

Relationship between Molecular Distance-Edge Vector and ¹³C Chemical Shifts of Carbonyl Compounds

PDF

可视化

摘要/Abstract

引用本文

使用本文

参考文献

相关文章 15

编辑推荐

Metrics

本文评价

[1]	王亚兰, 王晓静, 王志伟. 阿齐沙坦的波谱学数据及结构确证[J]. 波谱学杂志, 2019, 36(3): 350-358.
[2]	汤衡, Gilbert NSHOGOZA, 刘明清, 刘亚茜, 阮科, 马荣声, 高佳. 基于片段的核磁共振筛选方法识别NSD1 SET结构域的全新苗头化合物[J]. 波谱学杂志, 2019, 36(2): 148-154.
[3]	武亚新, 曹晨忠, 滕丽丽. 由¹³C NMR化学位移测定值确定烷烃生成焓[J]. 波谱学杂志, 2019, 36(1): 65-73.
[4]	张明光, 冯小虎, 于水涛, 吉小龙, 陈再新. 盐酸贝西沙星的波谱学数据与结构确证[J]. 波谱学杂志, 2018, 35(3): 374-384.
[5]	葛玉玮, 刘买利, 甘哲宏, 李从刚. 质子化学位移各向异性的测量[J]. 波谱学杂志, 2018, 35(2): 255-267.
[6]	李双利, 朱勤俊, 刘买利, 杨运煌. 蛋白质分子核磁共振谱峰的特性及其化学位移归属[J]. 波谱学杂志, 2017, 34(2): 137-147.
[7]	付娟, 吴能友, 邬黛黛, 苏秋成. 甲烷水合物的固体核磁共振碳谱与激光拉曼光谱研究[J]. 波谱学杂志, 2017, 34(2): 148-155.
[8]	王菲菲, 张聿梅, 何轶, 戴忠, 马双成, 刘斌. 雷酚内酯的波谱学数据与结构确证[J]. 波谱学杂志, 2017, 34(1): 35-42.
[9]	曹朝暾, 罗青青, 曹晨忠. 取代基效应对二芳基硝酮CH=N(O)桥基¹H NMR化学位移的影响[J]. 波谱学杂志, 2017, 34(1): 69-77.
[10]	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.
[11]	刘雅琴, 何玲, 余明新. 新型拟肽cyclo[-RGD-ψ(triazole)-GD-]波谱学数据与结构确证[J]. 波谱学杂志, 2016, 33(2): 337-344.
[12]	王强, 李玉江, 陶乐, 郭晓河, 董黎红, 宋传君, 常俊标. 胞苷盐酸盐的质子化位置研究[J]. 波谱学杂志, 2016, 33(2): 281-287.
[13]	宋爱华1，张延峰2，沙沂1，高源3，李宁3，马跃平3*. 富马酸替诺福韦二吡呋酯波谱数据与结构确证[J]. 波谱学杂志, 2015, 32(3): 542-550.
[14]	魏淑怡，潘韻如，曾天生，陈金榜*. 克雷伯氏肺炎杆菌内抗亚碲酸盐蛋白质TerZ 延伸环降低对钙离子亲合性[J]. 波谱学杂志, 2015, 32(2): 308-317.
[15]	KUMAR Sriramoju M 1，呂平江1，徐尚德1,2,3*. 以液体核磁共振波谱分析与帕金森氏病相关的I93M 突变对人类泛素碳端水解酶结构的影响[J]. 波谱学杂志, 2015, 32(2): 329-341.