大学生研究性教学实践——以芳香烃核磁共振的理论计算为例

doi:10.3866/PKU.DXHX202205012

Abstract

Abstract:

To improve the self-learning ability and inquiry-based learning skills of undergraduates, we guided the students to study the concepts and data in the literature, performed first-principles simulations, analyzed and discussed the relevant results of aromatic hydrocarbon molecules. Through this research-oriented teaching, students understood that the chemical shift is influenced by different substituent groups, chemical structures, and the states of matter, and that spin-spin coupling constants indicate chemical structures. In addition, the students gained further understanding of the relationship between the microscopic structure and macroscopic properties. Moreover, research-oriented teaching improves students' self-learning skills and ability to apply knowledge and solve problems. Furthermore, this activity type improves students' ability to explore in-depth knowledge and develop critical thinking skills, which are essential for training innovative scientists and engineers.

Key words: Aromatic hydrocarbon molecules, Nuclear magnetic resonance, Chemical shift, Research-oriented teaching

Chunfang Zhang, Ziyang Liu, Zilin Zhao, Lüjie Fan, Zan Zhang, Yanli Shang, Shuying Huo, Gang Ma. Exploration of Research-Oriented Teaching in Colleges: Theoretical Calculations and Simulations of Nuclear Magnetic Resonance for Aromatic Hydrocarbons[J].University Chemistry, 2022, 37(12): 2205012.

Figures/Tables 6

元素	b-b	b-m	标I	标II	exp. ^[24]	电荷	元素	b-b	b-m	标I	标II	exp. ^[24]	电荷
苯							苯酚
1/3C	131.83	146.98	127.33	128.77	128.36	?0.10	1/3C	127.44	131.75	123.02	115.94	115.48	?0.13
2C	131.83	146.98	127.33	128.77	128.36	?0.10	2C	163.47	176.20	158.35	153.29	155.02	0.15
4/6C	131.83	146.98	127.33	128.77	128.36	?0.10	4/6C	132.66	148.88	128.14	129.45	129.79	?0.10
5C	131.83	146.98	127.33	128.77	128.36	?0.10	5C	127.75	137.54	123.33	120.80	121.09	?0.10
7/8H	7.39	8.43	7.33	7.47	7.34	0.10	7/8H	7.22	7.37	7.16	6.59	6.84	0.09
9/11H	7.39	8.43	7.33	7.47	7.34	0.10	9/11H	7.33	8.17	7.26	7.27	7.24	0.10
10H	7.39	8.43	7.33	7.47	7.34	0.10	10H	7.13	7.13	7.07	6.98	6.93	0.09
12H	7.39	8.43	7.33	7.47	7.34	0.10	13H	2.11	4.35	2.15	4.00	5.35	0.25
苯胺							硝基苯
1/3C	115.61	142.02	123.26	113.97	115.07	?0.08	1C	127.44	141.73	123.02	124.33	123.46	?0.05
2C	152.74	173.96	155.78	145.53	146.51	0.10	2C	154.41	168.98	149.46	147.23	148.30	0.11
4/6C	132.92	155.38	134.61	129.48	129.26	?0.10	3C	127.44	141.73	123.02	124.33	123.46	?0.05
5C	120.40	144.62	124.25	118.53	118.39	?0.11	4C	132.08	147.23	127.57	128.95	129.43	?0.10
7/8H	6.51	179.14	161.95	6.68	6.67	0.08	5C	138.06	155.07	133.43	135.54	134.71	?0.07
9/11H	7.12	19.56	17.95	7.21	7.14	0.09	6C	132.08	147.23	127.57	128.95	129.43	?0.10
10H	6.63	8.02	7.04	6.81	6.75	0.09	7H	8.38	9.50	8.29	8.41	8.24	0.14
13H	2.78	8.36	7.25	3.31	3.54	0.20	8H	8.38	9.50	8.29	8.41	8.24	0.14
							9H	7.51	8.50	7.44	7.55	7.55	0.11
							10H	7.66	8.69	7.58	7.72	7.71	0.11
							11H	7.51	8.50	7.44	7.55	7.55	0.11
苯甲醛							邻乙酰氧基苯甲酸
1C	137.15	146.66	132.54	128.47	129.68	?0.05	1C	127.68	142.02	123.26	124.57	124.01	?0.06
2C	140.34	156.50	135.67	136.74	136.47	?0.18	2C	160.85	173.96	155.78	151.41	151.28	0.12
3C	131.03	152.92	126.54	133.73	129.68	?0.02	3C	126.26	140.63	121.86	123.41	122.26	?0.15
4C	132.34	147.45	127.83	129.14	128.98	?0.10	4C	139.26	155.38	134.61	135.81	132.51	?0.03
5C	137.83	153.61	133.21	134.31	134.43	?0.07	5C	128.69	144.62	124.25	126.76	126.17	?0.09
6C	132.10	147.27	127.59	125.63	128.98	?0.10	6C	138.46	154.71	133.82	135.24	134.90	?0.073
12C	191.28	212.17	185.61	183.53	192.28	0.23	11C	167.15	179.14	161.95	155.77	170.20	0.425
7H	7.61	8.74	7.54	7.76	7.87	0.10	12C	167.71	179.49	162.50	156.06	169.76	0.329
8H	8.26	9.31	8.18	8.25	7.87	0.11	13C	20.27	19.56	17.95	21.67	20.99	?0.357
9H	7.55	8.50	7.48	7.55	7.51	0.11	7H	7.10	8.02	7.04	7.15	7.14	0.113
10H	7.59	8.63	7.52	7.67	7.61	0.11	8H	8.33	9.38	8.24	8.31	8.12	0.120
11H	7.56	8.74	7.49	7.71	7.51	0.10	9H	7.32	8.36	7.25	7.43	7.36	0.107
13H	10.12	10.99	9.50	9.68	10.00	0.06	10H	7.56	8.55	7.49	7.59	7.62	0.109
							14H	5.77	7.05	5.74	6.31	11.00	0.251
							15H	1.76	1.88	1.80	1.90	2.35	0.142

References 28

1	张春芳; 霍丙南; 韩琳玉; 姚宁; 沈福刚; 商艳丽; 孙素芳; 单金缓; 马志广. 化学教育(中英文), 2020, 41 (14), 96.
2	张春芳; 张翠妙; 李江涛; 韩琳玉; 顾芳; 王海军. 大学化学, 2019, 34 (6), 81.
3	张红; 霍树营; 任淑霞; 张春芳; 王海军. 实验室研究与探索, 2019, 38 (5), 136. doi: 10.3969/j.issn.1006-7167.2019.05.034
4	刘伟; 刘丽英; 刘清雅. 中国大学教学, 2021, (4), 44. doi: 10.3969/j.issn.1005-0450.2021.04.010
5	Jonas E. ; Kuhn S. ; Schlörer N. Magn. Reson. Chem. 2021, 60, 1021.
6	丁飞; 张翠; 邱晓航. 大学化学, 2021, 36 (7), 2012050.
7	Krivdin L. B. Prog. Nucl. Magn. Reson. Spectrosc. 2019, 112, 103.
8	王粉粉; 孙平川. 高分子学报, 2021, 52 (7), 18.
9	李骞; 唐亚林; 向俊锋. 波谱学杂志, 2021, 38 (1), 22.
10	Klepach T. ; Zhang W. ; Carmichael I. ; Serianni A. S. J. Org. Chem. 2008, 73 (12), 4376. doi: 10.1021/jo702204x
11	Anton S. M. ; Mikhail A. V. ; Peter M. T. Fuller. Nanotub. Car. N. 2020, 28 (3), 202. doi: 10.1080/1536383X.2019.1686622
12	喻志武; 郑安民; 王强; 黃信炅; 邓风; 刘尚斌. 波谱学杂志, 2010, 27 (4), 485. doi: 10.3969/j.issn.1000-4556.2010.04.001
13	王乃兴. 核磁共振谱学: 在有机化学中的应用, 北京: 化学工业出版社, 2015, 22- 76.
14	Tuttle T. ; Kraka E. ; Wu A. ; Cremer D. J. Am. Chem. Soc. 2004, 126 (16), 5093. doi: 10.1021/ja030246e
15	Cremer D. ; Kraka A. E. ; Wu A. ; Lüttke W. ChemPhysChem 2004, 5 (3), 349. doi: 10.1002/cphc.200300987
16	Ambati J. ; Rankin S. E. J. Phys. Chem. A 2010, 114 (16), 5279. doi: 10.1021/jp911327a
17	Becker J. ; Comotti A. ; Simonetta R. ; Suzanna P. ; Saalwachter K. J. Phys. Chem. B 2005, 109 (49), 23285. doi: 10.1021/jp054795d
18	Ditchfield R. Mol. Phys. 1974, 27 (4), 789. doi: 10.1080/00268977400100711
19	Keith T. A. ; Bader R. Chem. Phys. Lett. 1993, 210 (1-3), 223. doi: 10.1016/0009-2614(93)89127-4
20	苏永超; 郑安民; 李申慧; 陈雷; 邓风. 波谱学杂志, 2006, 23 (3), 293. doi: 10.3969/j.issn.1000-4556.2006.03.002
21	谈谈如何又好又快地计算NMR化学位移. [2022-05-20]. http://bbs.keinsci.com/thread-4434-1-1.html
22	标度法参数选择表网址. [2022-05-20]. http://cheshirenmr.info
23	Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Scalmani, G.; Barone, V.; Petersson, G. A.; Nakatsuji, H.; et al. Gaussian 09, Rev. B. 01; Gaussian, lnc. : Wallingford, CT, USA, 2010.
24	SDBS: NIMC有机物谱图库网址. [2022-05-20]. https://sdbs.db.aist.go.jp/sdbs/cgi-bin/cre_index.cgi?lang=eng
25	Thonhauser T. ; Ceresoli D. ; Marzari N. Int. J. Quantum Chem. 2009, 109 (14), 3336. doi: 10.1002/qua.21941
26	Nagano M. ; Hasegawa T. ; Myoujin N. ; Yamaguchi J. ; Koinuma H. Jpn. J. Appl. Phys. 2004, 43, 315. doi: 10.1143/JJAP.43.315
27	Hansen P. E. ; Berg A. Org. Magn. Reson. 1979, 12 (1), 50. doi: 10.1002/mrc.1270120111
28	Dodziuk H. ; Jaszuński M. ; Schilf W. Magn. Reson. Chem. 2005, 43 (8), 639. doi: 10.1002/mrc.1598

时间安排	任务内容	执行分配	具体实践内容
提前准备	小组分配、题目互选	教学目标	理解核磁共振的基本概念和发展
提前准备	小组分配、题目互选	教学内容	核磁技术化学位移、耦合常数等具体内容
第一周	学生实践为主，教师指导为辅。定期交流进展	学生实践	调研文献，明确目标体系——芳香族化合物
第一周	学生实践为主，教师指导为辅。定期交流进展	教师指导	建模、化学位移及耦合常数计算的实施方法
第三周	学生实践，定期交流进展	学生实践	目标分子建模及化学位移、耦合常数计算
第四周	学生总结展示、教师点评	教师指导	组织讨论，并指导对结果的分析
第四周	学生总结展示、教师点评	学生实践	汇总计算结果、书写报告以及结果展示
第五周	教师反思	教师反思	总结成效，反思教学过程并提出改进意见

化合物	¹J(C, C)	calc.	exp. ^[27]	²J(C, C)	calc.	exp. ^[27]	³J(C, C)	calc.	exp. ^[27]	⁴J(C, C)	calc.	exp. ^[27]
	1C, 2C	68.60	60.40	1C, 3C	?1.19		1C, 4C	7.86		1C, 15C	?0.33
	1C, 6C	59.65		1C, 5C	?1.85	?2.45	1C, 10C	5.43	5.51	1C, 11C	?0.15
	2C, 3C	62.26	55.87	2C, 4C	0.04	0.20	2C, 5C	8.02		2C, 14C	?1.54	?1.47
	3C, 4C	57.63		2C, 10C	2.43		2C, 11C	2.86
	12C, 9C	59.73		12C, 10C	?4.02		25C, 26C	17.10		9C, 5C	?5.43
	9C, 10C	73.77		9C, 1C	?3.85		2C, 5C	13.99		10C, 25C	?4.85
	10C, 1C	62.76		10C, 2C	?1.51		10C, 11C	9.66		1C, 17C	?3.52
	1C, 2C	74.67		10C, 6C	?2.10		1C, 12C	9.79		1C, 26C	?6.52
	1C, 6C	57.82		1C, 3C	?4.13		1C, 4C	9.62
	2C, 3C	69.45		2C, 25C	?5.70		9C, 2C	10.05
	3C, 25C	72.82		2C, 6C	?4.53		10C, 3C	7.87
	3C, 4C	57.63		2C, 4C	?4.21		1C, 25C	10.96
				3C, 17C	?4.48		5C, 10C	6.57
				4C, 25C	?5.23		5C, 25C	11.04

[1]	Xudong Liu, Huili Fan, Junping Xiao, Min Yang, Yan Li. Teaching Approaches to the A_E + A_N Mechanism of Electrophilic Addition Reactions between Olefins and Inorganic Acids in Organic Chemistry [J]. University Chemistry, 2025, 40(7): 367-372.
[2]	Jiying Liu, Zehua Li, Wenjing Zhang, Donghui Wei. Molecular Orbital and Nucleus-Independent Chemical Shift Calculations for C₆H₆ and B₁₂H₁₂^2-: A Computational Chemistry Experiment [J]. University Chemistry, 2025, 40(3): 186-192.
[3]	Haiyang Jin, Yonghai Hui, Yongfei Zhang, Lijun Gao, Yun Wang. Application and Exploration of Nuclear Magnetic Resonance Spectrometer in Undergraduate Basic Laboratory Teaching [J]. University Chemistry, 2025, 40(3): 245-250.
[4]	Jing Wu, Wei Wang, Jingfeng Lan, E Yu, Qiaosheng Pu. New Life of an Old Spectrometer: An Innovative Experiment Based on the Digitization of an Obsolete Instrument [J]. University Chemistry, 2025, 40(2): 59-66.
[5]	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.
[6]	Hao Wu, Zhen Liu, Dachang Bai. ¹H NMR Spectrum of Amide Compounds [J]. University Chemistry, 2024, 39(3): 231-238.
[7]	Shuang Yang, Qun Wang, Caiqin Miao, Ziqi Geng, Xinran Li, Yang Li, Xiaohong Wu. Ideological and Political Education Design for Research-Oriented Experimental Course of Highly Efficient Hydrogen Production from Water Electrolysis in Aerospace Perspective [J]. University Chemistry, 2024, 39(11): 269-277.
[8]	Jinkang Jin, Yidian Sheng, Ping Lu, Zhan Lu. Introducing a Website for Learning Nuclear Magnetic Resonance (NMR) Spectrum Analysis [J]. University Chemistry, 2024, 39(11): 388-396.
[9]	Yaofeng Yuan, Baoxu Wang, Liangsen Huang, Jiajia Cheng. Analysis of Isomerization Products by Proton Nuclear Magnetic Resonance Spectroscopy [J]. University Chemistry, 2022, 37(3): 2105010-.
[10]	Zhonghua Xi, Dadong Lu, Jie Dai, Tao Ye, Wenwei Zhang. Determination of Enantiomeric Purity of Binaphthol by NMR Method [J]. University Chemistry, 2022, 37(2): 2109027-.
[11]	Zhanxiang Liu, Zhenjun Mao, Dongbei Shao, Minrui Qin, Guochun Lan, Huangju Cai, Huarong Zhao. Teaching Practice of Organic Synthesis Laboratory Course Based on the Combination of Research and Systematicness [J]. University Chemistry, 2022, 37(2): 2109076-.
[12]	Zhonghua Ma, Xiufang Cao, Hong Jiang, Jimei Ma. An Attempt on the Teaching Basic Concepts of the Nuclear Magnetic Resonance [J]. University Chemistry, 2021, 36(4): 2004004-.
[13]	Wenxue Chen, Shasha Liu, Huixiang Li. Improvement of the Determination of Components in Paracetamol, Aminophenazone, Caffeine and Chlorpheniramine Maleate Tablet Using ¹H Nuclear Magnetic Resonance Spectroscopy [J]. University Chemistry, 2021, 36(2): 2002045-.
[14]	Jianwei Dong,Xuejiao Li,Le Cai,Yingchun Miao. Teaching Undergraduate Student Curriculum "Spectral Analysis" by the NMR Analysis of Dehydrocurvularin [J]. University Chemistry, 2020, 35(3): 113-119.
[15]	Liping WANG. Discussion on the Teaching Effects of Lectures in English Based on Questionnaire Surveys of Organic Material Chemistry [J]. University Chemistry, 2019, 34(4): 26-33.

Exploration of Research-Oriented Teaching in Colleges: Theoretical Calculations and Simulations of Nuclear Magnetic Resonance for Aromatic Hydrocarbons

RichHTML

PDF

Like

Knowledge

Abstract

Cite this article

share this article

Figures/Tables 6

References 28

Related Articles 15

Metrics

Recommended 0