Citation:
Yilun Li, Yaofeng Yuan, Keyin Ye. Cage-Type Stereoelectronic Effects of Perfluorocubane[J]. University Chemistry,
;2023, 38(11): 126-130.
doi:
10.3866/PKU.DXHX202304025
-
As an essential component of fundamental organic chemistry theory, stereoelectronic effects, including the common gauche and anomeric effects, have been intensively investigated and discussed in undergraduate courses. Nevertheless, with the precise prediction and successful synthesis of perfluorocubane, a new cage-type stereoelectronic effect has attracted considerable attention from chemists. Herein, we briefly review the development of stereoelectronic effects, including their wide-ranging applications in organic chemistry. In particular, we highlight recent investigations on perfluorocubane synthesis and discuss the interesting cage-type stereoelectronic effects. The positive interplay between the scientific frontiers and the organic chemistry course will significantly influence the global perspective of students by expanding their knowledge of organic chemistry, and the fundamental concepts and advanced applications of stereoelectronic effects.
-
Keywords:
- Stereoelectronic effects,
- Organic synthesis,
- Perfluorocubane
-
-
-
[1]
Alabugin, I. V. Stereoelectronic Effects:A Bridge Between Structure and Reactivity; John Wiley & Sons, Ltd.:New York, NY, USA, 2016.
-
[2]
-
[3]
-
[4]
-
[5]
Edward, J. T. Chem. Ind. 1955, 3, 1102.
-
[6]
-
[7]
-
[8]
Pophristic, V.; Goodman, L. Nature 2001, 411, 565.
-
[9]
Weinhold, F. Nature 2001, 411, 539.
-
[10]
Alabugin, I. V.; Gilmore, K. M.; Peterson, P. W. Comput. Mol. Sci. 2011, 1, 109.
-
[11]
Irikura, K. K. J. Phys. Chem. A 2008, 112, 983.
-
[12]
Kato, T.; Yamabe, T. J. Chem. Phys. 2004, 120, 1006.
-
[13]
Sugiyama, M.; Akiyama, M.; Yonezawa, M.; Komaguchi, K.; Higashi, K.; Nozaki, K.; Okazoe, T. Science 2022, 377, 756.
-
[14]
Berski, S.; Gordon, A. J.; Latajka, Z.; J. Phys. Chem. A 2014, 118, 4147.
-
[15]
Bent, H. A. Chem. Rev. 1961, 61, 275.
-
[16]
Bauzá, A.; Mooibroek, T. J.; Frontera, A. Phys. Chem. Chem. Phys. 2014, 16, 19192.
-
[17]
Dai, X.- L.; Schulz, D. L.; Braun, C. W.; Ugrinov, A.; Boudjouk, P. Organometallics 2010, 29, 2203.
-
[18]
Dai, X.- L.; Choi, S.-B.; Braun, C. W.; Vaidya, P.; Kilina, S.; Ugrinov, A.; Schulz, D. L.; Boudjouk, P. Inorg. Chem. 2011, 50, 4047.
-
[1]
-
-
-
[1]
Aidang Lu , Yunting Liu , Yanjun Jiang . Comprehensive Organic Chemistry Experiment: Synthesis and Characterization of Triazolopyrimidine Compounds. University Chemistry, 2024, 39(8): 241-246. doi: 10.3866/PKU.DXHX202401029
-
[2]
Shiyan Cheng , Yonghong Ruan , Lei Gong , Yumei Lin . Research Advances in Friedel-Crafts Alkylation Reaction. University Chemistry, 2024, 39(10): 408-415. doi: 10.12461/PKU.DXHX202403024
-
[3]
Tingting Yu , Si Chen , Lianglong Sun , Tongtong Shi , Kai Sun , Xin Wang . Comprehensive Experimental Design for the Photochemical Synthesis, Analysis, and Characterization of Difluoropyrroles. University Chemistry, 2024, 39(11): 196-203. doi: 10.3866/PKU.DXHX202401022
-
[4]
Yaqin Zheng , Lian Zhuo , Meng Li , Chunying Rong . Enhancing Understanding of the Electronic Effect of Substituents on Benzene Rings Using Quantum Chemistry Calculations. University Chemistry, 2025, 40(3): 193-198. doi: 10.12461/PKU.DXHX202406119
-
[5]
Feng Sha , Xinyan Wu , Ping Hu , Wenqing Zhang , Xiaoyang Luan , Yunfei Ma . Design of Course Ideology and Politics for the Comprehensive Organic Synthesis Experiment of Benzocaine. University Chemistry, 2024, 39(2): 110-115. doi: 10.3866/PKU.DXHX202307082
-
[6]
Xinyu Zhu , Meili Pang . Application of Functional Group Addition Strategy in Organic Synthesis. University Chemistry, 2024, 39(3): 218-230. doi: 10.3866/PKU.DXHX202308106
-
[7]
Tianyun Chen , Ruilin Xiao , Xinsheng Gu , Yunyi Shao , Qiujun Lu . Synthesis, Crystal Structure, and Mechanoluminescence Properties of Lanthanide-Based Organometallic Complexes. University Chemistry, 2024, 39(5): 363-370. doi: 10.3866/PKU.DXHX202312017
-
[8]
Jiaojiao Yu , Bo Sun , Na Li , Cong Wen , Wei Li . Improvement of Classical Organic Experiment Based on the “Reverse-Step Optimization Method”: Taking Synthesis of Ethyl Acetate as an Example. University Chemistry, 2025, 40(3): 333-341. doi: 10.12461/PKU.DXHX202405177
-
[9]
Jingjing QING , Fan HE , Zhihui LIU , Shuaipeng HOU , Ya LIU , Yifan JIANG , Mengting TAN , Lifang HE , Fuxing ZHANG , Xiaoming ZHU . Synthesis, structure, and anticancer activity of two complexes of dimethylglyoxime organotin. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1301-1308. doi: 10.11862/CJIC.20240003
-
[10]
Liang TANG , Jingfei NI , Kang XIAO , Xiangmei LIU . Synthesis and X-ray imaging application of lanthanide-organic complex-based scintillators. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1892-1902. doi: 10.11862/CJIC.20240139
-
[11]
Wenjie SHI , Fan LU , Mengwei CHEN , Jin WANG , Yingfeng HAN . Synthesis and host-guest properties of imidazolium-functionalized zirconium metal-organic cage. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 105-113. doi: 10.11862/CJIC.20240360
-
[12]
Yinwu Su , Xuanwen Zheng , Jianghui Du , Boda Li , Tao Wang , Zhiyan Huang . Green Synthesis of 1,3-Dibromoacetone Using Halogen Exchange Method: Recommending a Basic Organic Synthesis Teaching Experiment. University Chemistry, 2024, 39(5): 307-314. doi: 10.3866/PKU.DXHX202311092
-
[13]
Xiaoling LUO , Pintian ZOU , Xiaoyan WANG , Zheng LIU , Xiangfei KONG , Qun TANG , Sheng WANG . Synthesis, crystal structures, and properties of lanthanide metal-organic frameworks based on 2, 5-dibromoterephthalic acid ligand. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1143-1150. doi: 10.11862/CJIC.20230271
-
[14]
Yukun Chang , Haoqin Huang , Baolei Wang . Preparation of Trans-Cinnamic Acid via “One-Pot” Protocol of Aldol Condensation-Hydrolysis Reaction: Recommending an Improved Organic Synthesis Experiment. University Chemistry, 2024, 39(4): 322-328. doi: 10.3866/PKU.DXHX202309095
-
[15]
Hong CAI , Jiewen WU , Jingyun LI , Lixian CHEN , Siqi XIAO , Dan LI . Synthesis of a zinc-cobalt bimetallic adenine metal-organic framework for the recognition of sulfur-containing amino acids. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 114-122. doi: 10.11862/CJIC.20240382
-
[16]
Zelong LIANG , Shijia QIN , Pengfei GUO , Hang XU , Bin ZHAO . Synthesis and electrocatalytic CO2 reduction performance of metal-organic framework catalysts loaded with silver particles. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 165-173. doi: 10.11862/CJIC.20240409
-
[17]
Yuan Zheng , Quan Lan , Zhenggen Zha , Lingling Li , Jun Jiang , Pingping Zhu . Teaching Reform of Organic Synthesis Experiments by Introducing Reverse Thinking and Design Concepts: Taking the Synthesis of Cinnamic Acid Based on Retrosynthetic Analysis as an Example. University Chemistry, 2024, 39(6): 207-213. doi: 10.3866/PKU.DXHX202310065
-
[18]
Wenxiu Yang , Jinfeng Zhang , Quanlong Xu , Yun Yang , Lijie Zhang . Bimetallic AuCu Alloy Decorated Covalent Organic Frameworks for Efficient Photocatalytic Hydrogen Production. Acta Physico-Chimica Sinica, 2024, 40(10): 2312014-. doi: 10.3866/PKU.WHXB202312014
-
[19]
Aiai WANG , Lu ZHAO , Yunfeng BAI , Feng FENG . Research progress of bimetallic organic framework in tumor diagnosis and treatment. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1825-1839. doi: 10.11862/CJIC.20240225
-
[20]
Shicheng Yan . Experimental Teaching Design for the Integration of Scientific Research and Teaching: A Case Study on Organic Electrooxidation. University Chemistry, 2024, 39(11): 350-358. doi: 10.12461/PKU.DXHX202408036
-
[1]
Metrics
- PDF Downloads(3)
- Abstract views(775)
- HTML views(87)