Citation: Yang Wang, Shuangliang Liu, Jianbo Zhao. Exploring the mechanism of Diels-Alder reaction: a computational chemistry experiment for undergraduate students[J]. University Chemistry, ;2026, 41(7): 257-265. doi: 10.12461/PKU.DXHX202504061 shu

Exploring the mechanism of Diels-Alder reaction: a computational chemistry experiment for undergraduate students

Department of Material and Chemical Engineering, Zhengzhou University of Light Industry, Zhengzhou 450001, Henan Province, China

Corresponding author: Yang Wang, Jianbo Zhao,
Received Date: 15 April 2025
Revised Date: 28 July 2025

The Diels-Alder (D-A) reaction serves as a paradigmatic example of concerted pericyclic reactions, yet its mechanistic abstraction often poses challenges for student comprehension. This study presents an instructional experiment employing computational chemistry methodologies with Gaussian software, enabling students to investigate the concerted mechanism of D-A reactions through transition state structures and energetic analyses. By integrating theoretical computations with visualization techniques, this experimental design overcomes the constraints of conventional teaching approaches, significantly enhancing students’ dynamic understanding of reaction mechanisms and fostering their scientific research competencies.
- Diels-Alder reaction,
- Transition state,
- Reaction mechanism,
- Density functional theory
1. [1]
  O. Diels, K. Alder, Ber. Dtsch. Chem. Ges. 1929, 62, 2081.
2. [2]
  O. Diels, K. Alder, Ber. Dtsch. Chem. Ges. 1929, 62, 2087.
3. [3]
  O. Diels, K. Alder, Justus Liebigs Ann. Chem. 1928, 460, 98.
4. [4]
5. [5]
6. [6]
7. [7]
8. [8]
9. [9]
10. [10]
11. [11]
12. [12]
  M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, G. Scalmani, V. Barone, G.A. Petersson, H. Nakatsuji, et al., Gaussian 09, Revision B. 01, Gaussian, Inc.: Wallingford, CT, USA, 2010.
13. [13]
14. [14]
  T. Lu, Q.X. Chen, Chem. Methods 2021, 1(5), 231.
15. [15]
  L.R. Domingo, M. Ríos-Gutierrez, P. Perez, Molecules 2016, 21(6), 748.
16. [16]
  P.P. Zhou, P.W. Ayers, S.B. Liu, T.L. Li, Phys. Chem. Chem. Phys. 2012, 14(28), 9890.
17. [17]
  J. Ye, Y. Wang, Eur. J. Org. Chem. 2023, 26(32), e202300520.
18. [18]
  J. Ye, G.L. Huang, Y. Wang, New J. Chem. 2023, 47(35), 16636.
19. [19]
  Y.L. Luo, M. Zhao, Y. Wang, J. Phys. Chem. A 2024, 128(30), 6190.
20. [20]
  M.Q. Yang, Y. Wang, Mol. Catal. 2024, 567, 114445.
21. [21]
  Y.N. Wang, Y. Wang, New J. Chem. 2024, 48(25), 11360.
1. [1]
  Yiying Yang , Dongju Zhang . Elucidating the Concepts of Thermodynamic Control and Kinetic Control in Chemical Reactions through Theoretical Chemistry Calculations: A Computational Chemistry Experiment on the Diels-Alder Reaction. University Chemistry, 2024, 39(3): 327-335. doi: 10.3866/PKU.DXHX202309074
2. [2]
  Ling Fan , Meili Pang , Yeyun Zhang , Yanmei Wang , Zhenfeng Shang . Quantum Chemistry Calculation Research on the Diels-Alder Reaction of Anthracene and Maleic Anhydride: Introduction to a Computational Chemistry Experiment. University Chemistry, 2024, 39(4): 133-139. doi: 10.3866/PKU.DXHX202309024
3. [3]
  Jiajie Li , Xiaocong Ma , Jufang Zheng , Qiang Wan , Xiaoshun Zhou , Yahao Wang . Recent Advances in In-Situ Raman Spectroscopy for Investigating Electrocatalytic Organic Reaction Mechanisms. University Chemistry, 2025, 40(4): 261-276. doi: 10.12461/PKU.DXHX202406117
4. [4]
  Ronghao Zhao , Yifan Liang , Mengyao Shi , Rongxiu Zhu , Dongju Zhang . Investigation into the Mechanism and Migratory Aptitude of Typical Pinacol Rearrangement Reactions: A Research-Oriented Computational Chemistry Experiment. University Chemistry, 2024, 39(4): 305-313. doi: 10.3866/PKU.DXHX202309101
5. [5]
  Weina Wang , Lixia Feng , Fengyi Liu , Wenliang Wang . Computational Chemistry Experiments in Facilitating the Study of Organic Reaction Mechanism: A Case Study of Electrophilic Addition of HCl to Asymmetric Alkenes. University Chemistry, 2025, 40(3): 206-214. doi: 10.12461/PKU.DXHX202407022
6. [6]
  Wentao Lin , Wenfeng Wang , Yaofeng Yuan , Chunfa Xu . Concerted Nucleophilic Aromatic Substitution Reactions. University Chemistry, 2024, 39(6): 226-230. doi: 10.3866/PKU.DXHX202310095
7. [7]
  Zhi Chai , Huashan Huang , Xukai Shi , Yujing Lan , Zhentao Yuan , Hong Yan . Wittig反应的立体选择性. University Chemistry, 2025, 40(8): 192-201. doi: 10.12461/PKU.DXHX202410046
8. [8]
  Bolin Sun , Jie Chen , Ling Zhou . 乙烯型卤代烃的亲核取代反应. University Chemistry, 2025, 40(8): 152-157. doi: 10.12461/PKU.DXHX202410032
9. [9]
  Hongting Yan , Aili Feng , Rongxiu Zhu , Lei Liu , Dongju Zhang . Reexamination of the Iodine-Catalyzed Chlorination Reaction of Chlorobenzene Using Computational Chemistry Methods. University Chemistry, 2025, 40(3): 16-22. doi: 10.12461/PKU.DXHX202403010
10. [10]
  Aili Feng , Xin Lu , Peng Liu , Dongju Zhang . Computational Chemistry Study of Acid-Catalyzed Esterification Reactions between Carboxylic Acids and Alcohols. University Chemistry, 2025, 40(3): 92-99. doi: 10.12461/PKU.DXHX202405072
11. [11]
  Guowen Xing , Guangjian Liu , Le Chang . Five Types of Reactions of Carbonyl Oxonium Intermediates in University Organic Chemistry Teaching. University Chemistry, 2025, 40(4): 282-290. doi: 10.12461/PKU.DXHX202407058
12. [12]
  Wanping Chen . Construction of Knowledge Logic and Discovery through Reasoning: Summarizing the Reaction Patterns of Reactive Metals with Oxygen. University Chemistry, 2026, 41(2): 95-102. doi: 10.12461/PKU.DXHX202503108
13. [13]
  Hao Wu , Fengqi Li , Xinwei Shi , Haifeng Bian , Qing Zhou , Shunshun Jia , Yujie Ma , Jian Gu , Jingzi Zhang , Shuijian He , Xiangkang Meng . Machine-learning guides discovery of multi-principal element alloys as electrocatalyst for hydrogen evolution reaction. Acta Physico-Chimica Sinica, 2026, 42(8): 100227-0. doi: 10.1016/j.actphy.2025.100227
14. [14]
  Wei Sun , Yongjing Wang , Kun Xiang , Saishuai Bai , Haitao Wang , Jing Zou , Arramel , Jizhou Jiang . CoP Decorated on Ti₃C₂T_x MXene Nanocomposites as Robust Electrocatalyst for Hydrogen Evolution Reaction. Acta Physico-Chimica Sinica, 2024, 40(8): 2308015-0. doi: 10.3866/PKU.WHXB202308015
15. [15]
  Hao XU , Ruopeng LI , Peixia YANG , Anmin LIU , Jie BAI . Regulation mechanism of halogen axial coordination atoms on the oxygen reduction activity of Fe-N₄ site: A density functional theory study. Chinese Journal of Inorganic Chemistry, 2025, 41(4): 695-701. doi: 10.11862/CJIC.20240302
16. [16]
  Jiabo Huang , Quanxin Li , Zhongyan Cao , Li Dang , Shaofei Ni . Elucidating the Mechanism of Beckmann Rearrangement Reaction Using Quantum Chemical Calculations. University Chemistry, 2025, 40(3): 153-159. doi: 10.12461/PKU.DXHX202405172
17. [17]
  Xinwan Zhao , Yue Cao , Minjun Lei , Zhiliang Jin , Tsubaki Noritatsu . Constructing S-scheme heterojunctions by integrating covalent organic frameworks with transition metal sulfides for efficient noble-metal-free photocatalytic hydrogen evolution. Acta Physico-Chimica Sinica, 2025, 41(12): 100152-0. doi: 10.1016/j.actphy.2025.100152
18. [18]
  Anqi LI , Wenjing YANG , Xueming LI , Yanfong REN . Performance and mechanism of a foam Ti/FeCo-Fe₂O₃-CoFe₂O₄/SnO₂-Sb anode for synergistic activation of peroxymonosulfate toward degradation of organic pollutants. Chinese Journal of Inorganic Chemistry, 2026, 42(5): 944-958. doi: 10.11862/CJIC.20250323
19. [19]
  Kaifu Zhang , Shan Gao , Bin Yang . Application of Theoretical Calculation with Fun Practice in Raman Spectroscopy Experimental Teaching. University Chemistry, 2025, 40(3): 62-67. doi: 10.12461/PKU.DXHX202404045
20. [20]
  Jie ZHAO , Sen LIU , Qikang YIN , Xiaoqing LU , Zhaojie WANG . Theoretical calculation of selective adsorption and separation of CO₂ by alkali metal modified naphthalene/naphthalenediyne. Chinese Journal of Inorganic Chemistry, 2024, 40(3): 515-522. doi: 10.11862/CJIC.20230385

Get Citation

PDF

XML

Metrics

PDF Downloads(1)
Abstract views(90)
HTML views(19)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142