Citation: Lei Shi. Nucleophilicity and Electrophilicity of Radicals[J]. University Chemistry, ;2024, 39(11): 131-135. doi: 10.3866/PKU.DXHX202402018 shu

Nucleophilicity and Electrophilicity of Radicals

  • Received Date: 4 February 2024
    Revised Date: 20 March 2024

  • Radical philicity and polar effects are key concepts underpinning radical reactivity and selectivity. In general, the radical species can be divided into two classes, namely, electrophilic and nucleophilic, on the basis of its reactivity, atom electronegativity, and stability of the resulting species through electron gain or loss. In this article we aim to establish guidelines for understanding radical philicity from different carbon-centered and heteroatom-centered radicals and we accompany our discussion with representative synthetic examples.
  • 加载中
    1. [1]

      Kolbe, H. Justus Liebigs Ann. Chem. 1848, 64, 339.

    2. [2]

      Gomberg, M. J. Am. Chem. Soc. 1900, 22, 757.

    3. [3]

      Walling, C. Tetrahedron 1985, 41, 3887.

    4. [4]

      Ingold, K. U. Pure Appl. Chem. 1997, 69, 241.

    5. [5]

      Yan, M.; Lo, J. C.; Edwards, J. T.; Baran, P. S. J. Am. Chem. Soc. 2016, 138, 12692.

    6. [6]

      Parsaee, F.; Senarathna, M. C.; Kannangara, P. B.; Alexander, S. N.; Arche, P. D. E.; Welin, E. R. Nat. Rev. Chem. 2021, 5, 486.

    7. [7]

      Chattaraj, P. K.; Giri, S.; Duley, S. Chem. Rev. 2011, 111, PR43.

    8. [8]

      Ruffoni, A.; Mykura, R. C.; Bietti, M.; Leonori, D. Nat. Syn. 2022, 1, 682.

    9. [9]

      Roberts, B. P. Chem. Soc. Rev. 1999, 28, 25.

    10. [10]

    11. [11]

      Hu, A.; Guo, J.-J.; Pan, H.; Zuo, Z. Science 2018, 361, 668.

    12. [12]

      Laudadio, G.; Deng, Y.; Van Der Wal, K.; Ravelli, D.; Nuño, M.; Fagnoni, M.; Guthrie, D.; Sun, Y.; Noël, T. Science 2020, 369, 6499.

    13. [13]

      Kariofillis, S. K.; Shields, B. J.; Tekle-Smith, M. A.; Zacuto, M. J.; Doyle, A. G. J. Am. Chem. Soc. 2020, 142, 7683.

    14. [14]

      Allen, L. C. J. Am. Chem. Soc. 1998, 111, 9003.

    15. [15]

      Héberger, K.; Lopata, A. J. Org. Chem. 1998, 63, 8646.

    16. [16]

      De Vleeschouwer, F.; Van Speybroeck, V.; Waroquier, M.; Geerlings, P.; De Proft, F. Org. Lett. 2007, 9, 2721.

    17. [17]

      Paul, V.; Roberts, B. P. J. Chem. Soc. Chem. Commun. 1987, 1322.

    18. [18]

      Liu, J.; Wu, S.; Yu, J.; Lu, C.; Wu, Z.; Wu, X.; Xue, X.-S.; Zhu, C. Angew. Chem. Int. Ed. 2020, 59, 8195.

    19. [19]

      Han, S.; Samony, K. L.; Nabi, R. N.; Bache, C. A.; Kim, D. K. J. Am. Chem. Soc. 2023, 145, 11530.

  • 加载中
    1. [1]

      Baitong Wei Jinxin Guo Xigong Liu Rongxiu Zhu Lei Liu . Theoretical Study on the Structure, Stability of Hydrocarbon Free Radicals and Selectivity of Alkane Chlorination Reaction. University Chemistry, 2025, 40(3): 402-407. doi: 10.12461/PKU.DXHX202406003

    2. [2]

      CCS Chemistry | 超分子活化底物自由基促进高效选择性光催化氧化

      . CCS Chemistry, 2025, 7(10.31635/ccschem.025.202405229): -.

    3. [3]

      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

    4. [4]

      Yuan GAOYiming LIUChunhui WANGZhe HANChaoyue FANJie QIU . A hexanuclear cerium oxo cluster stabilized by furoate: Synthesis, structure, and remarkable ability to scavenge hydroxyl radicals. Chinese Journal of Inorganic Chemistry, 2025, 41(3): 491-498. doi: 10.11862/CJIC.20240271

    5. [5]

      Yue Zhao Yanfei Li Tao Xiong . Copper Hydride-Catalyzed Nucleophilic Additions of Unsaturated Hydrocarbons to Aldehydes and Ketones. University Chemistry, 2024, 39(4): 280-285. doi: 10.3866/PKU.DXHX202309001

    6. [6]

      Min LIUHuapeng RUANZhongtao FENGXue DONGHaiyan CUIXinping WANG . Neutral boron-containing radical dimers. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 123-130. doi: 10.11862/CJIC.20240362

    7. [7]

      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

    8. [8]

      Daojuan Cheng Fang Fang . Exploration and Implementation of Science-Education Integration in Organic Chemistry Teaching for Pharmacy Majors: A Case Study on Nucleophilic Substitution Reactions of Alkyl Halides. University Chemistry, 2024, 39(11): 72-78. doi: 10.12461/PKU.DXHX202403105

    9. [9]

      Jiajia Li Xiangyu Zhang Zhihan Yuan Zhengyang Qian Jian Zhu . 3D Printing Based on Photo-Induced Reversible Addition-Fragmentation Chain Transfer Polymerization. University Chemistry, 2024, 39(5): 11-19. doi: 10.3866/PKU.DXHX202309073

    10. [10]

      Zijian Zhao Yanxin Shi Shicheng Li Wenhong Ruan Fang Zhu Jijun Jiang . A New Exploration of the Preparation of Polyacrylic Acid by Free Radical Polymerization Based on the Concept of Green Chemistry. University Chemistry, 2024, 39(5): 315-324. doi: 10.3866/PKU.DXHX202311094

    11. [11]

      Zhongyan Cao Shengnan Jin Yuxia Wang Yiyi Chen Xianqiang Kong Yuanqing Xu . Advances in Highly Selective Reactions Involving Phenol Derivatives as Aryl Radical Precursors. University Chemistry, 2025, 40(4): 245-252. doi: 10.12461/PKU.DXHX202405186

    12. [12]

      Danqing Wu Jiajun Liu Tianyu Li Dazhen Xu Zhiwei Miao . Research Progress on the Simultaneous Construction of C—O and C—X Bonds via 1,2-Difunctionalization of Olefins through Radical Pathways. University Chemistry, 2024, 39(11): 146-157. doi: 10.12461/PKU.DXHX202403087

    13. [13]

      Jiying Liu Zehua Li Wenjing Zhang Donghui Wei . Molecular Orbital and Nucleus-Independent Chemical Shift Calculations for C6H6 and B12H122-: A Computational Chemistry Experiment. University Chemistry, 2025, 40(3): 186-192. doi: 10.12461/PKU.DXHX202406085

    14. [14]

      Lina Feng Guoyu Jiang Xiaoxia Jian Jianguo Wang . Application of Organic Radical Materials in Biomedicine. University Chemistry, 2025, 40(4): 253-260. doi: 10.12461/PKU.DXHX202405171

    15. [15]

      Yinuo Wang Siran Wang Yilong Zhao Dazhen Xu . Selective Synthesis of Diarylmethyl Anilines and Triarylmethanes via Multicomponent Reactions: Introduce a Comprehensive Experiment of Organic Chemistry. University Chemistry, 2024, 39(8): 324-330. doi: 10.3866/PKU.DXHX202401063

    16. [16]

      Dongheng WANGSi LIShuangquan ZANG . Construction of chiral alkynyl silver chains and modulation of chiral optical properties. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 131-140. doi: 10.11862/CJIC.20240379

    17. [17]

      Jin Tong Shuyan Yu . Crystal Engineering for Supramolecular Chirality. University Chemistry, 2024, 39(3): 86-93. doi: 10.3866/PKU.DXHX202308113

    18. [18]

      Qiuting Zhang Fan Wu Jin Liu Zian Lin . Chromatographic Stationary Phase and Chiral Separation Using Frame Materials. University Chemistry, 2025, 40(4): 291-298. doi: 10.12461/PKU.DXHX202405174

    19. [19]

      Peiran ZHAOYuqian LIUCheng HEChunying DUAN . A functionalized Eu3+ metal-organic framework for selective fluorescent detection of pyrene. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 713-724. doi: 10.11862/CJIC.20230355

    20. [20]

      Xilin Zhao Xingyu Tu Zongxuan Li Rui Dong Bo Jiang Zhiwei Miao . Research Progress in Enantioselective Synthesis of Axial Chiral Compounds. University Chemistry, 2024, 39(11): 158-173. doi: 10.12461/PKU.DXHX202403106

Metrics
  • PDF Downloads(28)
  • Abstract views(1399)
  • HTML views(534)

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

  1. 本站搜索
  2. 百度学术搜索
  3. 万方数据库搜索
  4. CNKI搜索
Address:Zhongguancun North First Street 2,100190 Beijing, PR China Tel: +86-010-82449177-888
Powered By info@rhhz.net

/

DownLoad:  Full-Size Img  PowerPoint
Return