光学活性和手性光谱的溯源和发展

doi:10.3866/PKU.DXHX202105009

Abstract

Abstract:

This paper presents a comprehensive overview on the discovery and development of optical activity and chiroptical spectroscopy since the nineteenth century, with emphasis on the background and basic principles of the development of optical rotatory dispersion (ORD), electron circular dichroism (ECD) and vibrational circular dichroism (VCD) spectroscopy. Therein, the outstanding contributions of Chinese scientists Guangxian Xu and Yunjie Xu in the development of chiroptical spectroscopy are specifically mentioned.

Key words: History of optical activity and chiroptical spectroscopy, Optical rotatory dispersion (ORD), Electron circular dichroism (ECD), Vibrational circular dichroism (VCD)

Hui Zhang, Aihua Qi, Dan Li, Rongxing Li. Traceability and Development of Optical Activity and Chiroptical Spectroscopy[J].University Chemistry, 2022, 37(1): 2105009.

Figures/Tables 16

References 75

1	Berova N. ; Polavarapu P. L. ; Nakanishi K. ; Woody R. W. Comprehensive Chiroptical Spectroscopy Chichester, UK: John Wiley & Sons, Ltd., 2012.
2	齐爱华, 陈丰娇, 李荣兴. 手性光谱仪器的发展及其手性检测方法学//章慧, 何裕建. 分子手性. 厦门: 厦门大学出版社, 2021: 362-377.
3	Laur, P. A. Historical Overview. In Comprehensive Chiroptical Spectroscopy; Berova, N.; Polavarapu, P. L.; Nakanishi, K.; Woody, R. W. Eds.; John Wiley & Sons, Ltd. : Chichester, UK, 2012; pp. 3-35.
4	Mason S. F. Molecular Optical Activity and Chiral Discriminations Cambridge, UK: Cambridge University Press, 1982.
5	Nafie L. A. Vibrational Optical Activity: Principles and Applications Chichester, UK: John Wiley & Sons, Ltd., 2011, pp. 1- 34.
6	Barron L. D. Molecular Light Scattering and Optical Activity 2nd ed. Cambridge, UK: Cambridge University Press, 2004.
7	Crabbé P. Optical Rotatory Dispersion and Circular Dichroism in Organic Chemistry San Francisco, CA, USA: Holden-Day, Inc., 1965.
8	章慧. 大学化学, 2021, 36 (6), 2008054.
9	Pasteur L. Ann. Chim. Phys. 1850, 28 (3), 56.
10	Tobe Y. Mendeleev Commun. 2003, 13 (3), 93. doi: 10.1070/MC2003v013n03ABEH001803
11	Ramsay O. B. Stereochemistry London, UK: Heyden & Son Ltd., 1981.
12	Arndtsen A. Ann. Phys. 1858, 181 (10), 312. doi: 10.1002/andp.18581811010
13	Landolt H. Liebigs Ann. Chem. 1877, 189 (3), 241. doi: 10.1002/jlac.18771890302
14	Landolt H. Das Optische Drehungsvermögen Organischer Substanzen und die Praktischen Anwendungen Desselben Braunschweig, Germany: Vieweg und Sohn, 1879.
15	Haidinger W. Ann. Phys. 1847, 146 (4), 531. doi: 10.1002/andp.18471460404
16	Dove H. W. Ann. Phys. 1860, 186 (6), 279. doi: 10.1002/andp.18601860607
17	Perucca E. Ann. Phys. 1914, 350 (19), 463. doi: 10.1002/andp.19143501910
18	Perucca E. Nuovo Cimento 1919, 18 (1), 112. doi: 10.1007/BF02959865
19	Burkov V. I. ; Egorysheva A. V. ; Kargin Y. F. ; Mar'in A A. ; Fedotov E. V. Crystallogr. Rep. 2005, 50 (3), 461. doi: 10.1134/1.1927610
20	King, N. Amethyst. [2021-03-20]. https://www.mindat.org/min-198.html
21	Bolano, A. Amethyst: Characteristics and Properties. [2018-08-17]. https://sciencetrends.com/amethyst-characteristics-and-properties/
22	Cotton A. C. R. Hebd. Seances Acad. Sci. (Paris). 1895, 120, 989.
23	Cotton A. C. R. Hebd. Seances Acad. Sci. (Paris). 1895, 120, 1044.
24	Cotton A. J. Phys. Théor. Appl. 1896, 5 (1), 237.
25	Lifschitz J. Rec. Trav. Chim. Pays-Bas 1922, 41, 627. doi: 10.1002/recl.19220411003
26	Kahr B. ; Bing Y. ; Kaminsky W. ; Viterbo D. Angew. Chem. Int. Ed. 2009, 48 (21), 3744. doi: 10.1002/anie.200801840
27	Bing Y. ; Selassi D. ; Paradise R. H. ; Christine I. ; Kramer N. ; Sadilek M. ; Kaminsky W. ; Kahr B. J. Am. Chem. Soc. 2010, 132 (21), 7454. doi: 10.1021/ja1018892
28	Rosenfeld L. Z. Phys. 1929, 52 (3-4), 161. doi: 10.1007/BF01342393
29	Kuhn W. Z. Phys. Chem. 1936, B31 (1), 23.
30	Tschugaeff L. Trans. Faraday Soc. 1914, 10 (8), 70.
31	Nyholm R. S. Phys. Eng. Sci. 1967, 297 (1448), 2.
32	Ingold C. Proc. Roy. Soc. A 1967, 297 (1448), 171.
33	Polavarapu P. L. Chirality 2002, 14 (10), 768. doi: 10.1002/chir.10145
34	McCaffery A. J. ; Mason S. F. Mol. Phys. 1963, 6 (4), 359. doi: 10.1080/00268976300100411
35	Mason S. F. Proc. Roy. Soc. A 1967, 297 (1448), 3.
36	Beckmann C. O. ; Cohen K. J. Chem. Phys. 1936, 4 (12), 784.
37	Charney E. The Molecular Basis of Optical Activity, Optical Rotatory Dispersion and Circular Dichroism New York, NY, USA: John Wiley & Sons, 1979.
38	徐光宪. 化学学报, 1955, 21 (1), 14.
39	叶青; 黄艳红; 朱晶. 举重若重: 徐光宪传, 北京: 中国科学技术出版社, 2013.
40	章慧; 等. 配位化学——原理与应用, 北京: 化学工业出版社, 2009.
41	章慧. 大学化学, 2017, 32 (2), 1.
42	章慧. Cotton效应//黄培强. 有机人名反应、试剂与规则. 第2版. 北京: 化学工业出版社, 2019: 698-703.
43	李丹. 化合物的集成手性光谱及其应用研究[博士学位论文]. 厦门: 厦门大学, 2017.
44	Nafie, L. A. Infrared vibrational optical activity: measurement and instrumentation. In Comprehensive Chiroptical Spectroscopy; Berova, N., Polavarapu, P. L., Nakanishi, K., Woody, R. W., Eds.; John Wiley & Sons, Ltd. : Chichester, UK, 2012; pp. 115-146.
45	吴国祯. 分子振动光谱学原理, 北京: 清华大学出版社, 2018.
46	Bijvoet J. M. ; Peerdeman A. F. ; van Bommel A. J. Nature 1951, 168 (4268), 271. doi: 10.1038/168271a0
47	Mitchell S. The Cotton Effect and Related Phenomena London, UK: G. Bell & Sons, Ltd., 1933.
48	Kuhn W. ; Szabo A. Z. Phys. Chem. 1932,
49	Mason S. F. Quart. Rev. 1963, 17 (1), 206.
50	黄鸣龙. 旋光谱在有机化学中的应用, 上海: 上海科学技术出版社, 1963.
51	Taniguchi T. ; Monde K. J. Am. Chem. Soc. 2012, 134 (8), 3695. doi: 10.1021/ja3001584
52	Taniguchi T. ; Manai D. ; Shibata M. ; Itabashi Y. ; Monde K. J. Am. Chem. Soc. 2015, 137 (38), 12191. doi: 10.1021/jacs.5b05832
53	Covington C. L. ; Nicu V. P. ; Polavarapu P. L. J. Phys. Chem. A 2015, 119 (42), 10589. doi: 10.1021/acs.jpca.5b07940
54	伊莱尔, E. L.; 威伦, S. H.; 多伊尔, M. P. 基础有机立体化学. 邓并, 主译. 北京: 科学出版社, 2005: 483-550.
55	Nafie L. A. Vibrational Optical Activity: Principles and Applications Chichester, UK: John Wiley & Sons, Ltd., 2011, pp. 1- 34.
56	Sadlej J. S. ; Dobrowolski J. C. ; Rode J. E. Chem. Soc. Rev. 2010, 39 (5), 1478. doi: 10.1039/B915178H
57	Kuhn W. Trans. Faraday Soc. 1930, 26, 293. doi: 10.1039/tf9302600293
58	Holzwarth G. ; Chabay I. J. Chem. Phys. 1972, 57 (4), 1632.
59	Schellman J. A. J. Chem. Phys. 1973, 58 (7), 2882.
60	Holzwarth G. ; Hsu E. C. ; Mosher H. S. ; Faulkner T. R. ; Moscowitz A. J. Am. Chem. Soc. 1974, 96 (1), 251. doi: 10.1021/ja00808a042
61	Stephens P. J. ; Devlin F. J. ; Pan J. -J. Chirality 2008, 20 (5), 243.
62	Nafie L. A. ; Cheng J. C. ; Stephens P. J. J. Am. Chem. Soc. 1975, 97 (13), 3842. doi: 10.1021/ja00846a061
63	Nafie L. A. ; Keiderling T. A. ; Stephens P. J. J. Am. Chem. Soc. 1976, 98 (10), 2715. doi: 10.1021/ja00426a007
64	Devlin F. J. ; Stephens P. J. ; Besse P. Tetrahedron: Asymmetry 2005, 16 (8), 1557. doi: 10.1016/j.tetasy.2005.02.033
65	Buckingham A. D. ; Fowler P. W. ; Galwas P. A. Chem. Phys. 1987, 112 (1), 1. doi: 10.1016/0301-0104(87)85017-6
66	Stephens P. J. J. Phys. Chem. 2002, 89 (5), 748.
67	Cheeseman J. R. ; Frisch M. J. ; Devlin F. J. ; Stephens P. J. Chem. Phys. Lett. 1996, 252 (2), 211.
68	Yang G. ; Xu Y. ; Hou J.-B. ; Zhang H. ; Zhao Y. F. Chem. Eur. J. 2010, 16 (8), 2518. doi: 10.1002/chem.200902501
69	Yang, G.; Xu, Y.; Hou, J. -B.; Zhang, H.; Zhao, Y. -F. Dalton Trans. 2010, 39 (30), 6953.
70	Zhang Y. ; Poopari M. R. ; Cai X. ; Savin A. ; Dezhahang Z. ; Cheramy J. ; Xu Y. J. Nat. Prod. 2016, 79 (4), 1012. doi: 10.1021/acs.jnatprod.5b01082
71	Bader R. F. W. Acc. Chem. Res. 1985, 18 (1), 9. doi: 10.1021/ar00109a003
72	Losada M. ; Nguyen P. ; Xu Y. J. Phys. Chem. A 2008, 112 (25), 5621. doi: 10.1021/jp801996m
73	Thomas J. ; Sukhorukov O. ; Jäger W. ; Xu Y. Angew. Chem. Int. Ed. 2014, 53 (4), 1156. doi: 10.1002/anie.201308466
74	Perera A. S. ; Thomas J. ; Poopari M. R. ; Xu Y. Front. Chem. 2016, 4, 1.
75	Merten C. ; Xu Y. Angew. Chem. Int. Ed. 2013, 52 (7), 2073. doi: 10.1002/anie.201208685

[1]	Jiantuo Chen, Fanpeng Shang. Analysis and Tracing of Question 1 from the 38th China Chemistry Olympiad (Preliminary) [J]. University Chemistry, 2025, 40(10): 303-308.
[2]	Qingtao Niu, Xinyao Xu, Weiyue Yu, Shuxiang Meng, Zhiguo Lv, Manman Jin. Exploration and Practice of Science-Education Integration in Chemical Engineering Thermodynamics Teaching for Chemical Engineering Majors: A Case of Chemical Engineering Physical Property Data Estimation and Chemical Reaction Equilibrium [J]. University Chemistry, 2025, 40(10): 1-9.
[3]	Yutong Liu, Xuemin Jing. Research Progress on the Catalytic Conversion of Methane in the Context of the “Dual Carbon” Goals [J]. University Chemistry, 2025, 40(10): 101-113.
[4]	Zhusheng Huang, Wei Xue, Yongzheng Chang, Lianhui Wang, Zhimin Luo. Teaching Reform in Physical Chemistry Experiments: Cultivating Students’ Innovation and Practical Skills [J]. University Chemistry, 2025, 40(10): 10-16.
[5]	Linlin Wang, Gang Liu, Chunxiao Chai, Qingming Lu, Ying Ma. The Application of the 6S Concept in Standardized Management of Instrumental Analytical Chemistry Teaching Laboratories in Universities [J]. University Chemistry, 2025, 40(10): 186-193.
[6]	Yansong Xiao, Yi Huang, Xingxing Ma, Qiuling Song. The Matteson Reaction in Organic Synthesis: From Fundamentals to Frontiers [J]. University Chemistry, 2025, 40(10): 114-120.
[7]	Qian Wu, Yuanxia Lv, Zixuan Guo, Zhihao Zhao, Zhimin Zhang, Hongmei Lu. A Case Study and Practice of Research-Oriented Comprehensive Instrumental Analysis Laboratory Courses [J]. University Chemistry, 2025, 40(10): 194-202.
[8]	Yuyang Zhang, Yuqing Zhang, Quanxing Mao, Zixuan Chen, Ying Xiong. Application of Real-World Problem-Oriented Teaching Methods in Analytical Chemistry Course [J]. University Chemistry, 2025, 40(10): 17-22.
[9]	Yerong Chen, Bingbin Yang, Xinglei He, Yuqi Lin, Keyin Ye. Enzyme-Directed Evolution Enables Bioconversion of Organosilicon Compounds [J]. University Chemistry, 2025, 40(10): 121-129.
[10]	Peipei Zhu, Li Wang, Lili Chen, Xunfan Liao, Yiwang Chen. Intelligent Teaching in Analytical Chemistry: An Exploration Based on Knowledge Graphs [J]. University Chemistry, 2025, 40(10): 23-32.
[11]	Wenwen Zhang, Peichao Zhang, Conghao Gai, Xiaoyun Chai, Yan Zou, Qingjie Zhao. Unveiling Kinetics at Natural Abundance: ¹³C NMR Isotope Effect Experiments [J]. University Chemistry, 2025, 40(10): 203-207.
[12]	Yinuo Wang, Ziyu Liu, Hongxia Tan, Jun Tong, Dazhen Xu. Synthesis of Bromobenzoxazine: Introduce a Comprehensive Organic Chemistry Experiment Transformed from Undergraduate Research Innovation [J]. University Chemistry, 2025, 40(10): 208-216.
[13]	Shuting Zhuang, Lida Zhao. Teaching through Research: A Comprehensive Experiment on Carbon Quantum Dots from Microplastic Waste [J]. University Chemistry, 2025, 40(10): 217-224.
[14]	Feng Lin, Zhongxin Jin, Caiying Li, Cheng Shao, Yang Xu, Fangze Li, Siqi Liu, Ruining Gu. Preparation and Electrochemical Properties of Nickel Foam-Supported Ni(OH)₂-NiMoO₄ Electrode Material [J]. University Chemistry, 2025, 40(10): 225-232.
[15]	Ying Yang, Yonghan Wu, Zixuan Li, Lu Zhang, Rongqin Lin, Yefan Zhang, Jiquan Liu, Xiaohui Ning, Yan Li, Bin Cui. Visualization Simulation Experiment of Cyclic Voltammetry (CV) Based on Python [J]. University Chemistry, 2025, 40(10): 233-242.

Traceability and Development of Optical Activity and Chiroptical Spectroscopy

RichHTML

PDF

Like

Knowledge

Abstract

Cite this article

share this article

Figures/Tables 16

References 75

Related Articles 15

Metrics

Recommended 0