Citation: Li Man, Kang Huiying, Xue Xiao-Song, Cheng Jin-Pei. Computational Study of the Trifluoromethyl Radical Donor Abilities of CF₃ Sources[J]. Acta Chimica Sinica, ;2018, 76(12): 988-996. doi: 10.6023/A18080334 shu

Computational Study of the Trifluoromethyl Radical Donor Abilities of CF₃ Sources

a.
State Key Laboratory of Elemento-Organic Chemistry, College of Chemistry, Collaborative Innovation Center of Chemical Science and Engineering, Nankai University, Tianjin 300071, China
b.
Center of Basic Molecular Science, Department of Chemistry, Tsinghua University, Beijing 100084, China

Corresponding author: Xue Xiao-Song, xuexs@nankai.edu.cn
Received Date: 14 August 2018
Available Online: 8 December 2018
Fund Project: the State Key Laboratory on Elemento-Organic Chemistry the Fundamental Research Funds for the Central Universities the National Natural Science Foundation of China 21390400Collaborative Innovation Center of Chemical Science and Engineering (Tianjin) the National Natural Science Foundation of China 21772098Project supported by the National Natural Science Foundation of China (Nos. 21772098, 21390400), Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), the State Key Laboratory on Elemento-Organic Chemistry, and the Fundamental Research Funds for the Central Universities

Figures(9)

Organic compounds containing trifluoromethyl (CF₃) group(s) are widely prevalent in biochemical and medicinal science. This is mainly due to the fact that the trifluoromethyl group often improves the metabolic stability and lipophilicity of biologically active compounds. The need of efficient methods for the incorporation of this group into target molecules has spurred research to discover new, practical CF₃ sources. Among various CF₃ sources, the radical trifluoromethylating reagents has provided a strong driving force for the discovery of the novel trifluoromethylation reactions, and contributed enormously to the efficient synthesis of various CF₃-containing compounds. Although a wide variety of radical CF₃ sources are now available to organic chemists, little attention has been paid to assess their trifluoromethyl radical donor abilities (TR^·DA). Moreover, the available radical reagents show a very rich and diverse reactivity. The establishment of an extensive scale to quantify their CF₃ radical donating abilities should be of great value for both the rational design of novel reagents and the judicious selection of appropriate reagent to explore new radical reactions. Herein, we present a systematic computational study of the homolytic X―CF₃ bond dissociation enthalpies of 35 radical trifluoromethylating reagents by using the SMD-M06-2X/[6-311++G(2df, 2p)-Def2-QZVPPD]//SMD-M06-2X/[6-31+G(d)-LANL2DZ] method, aiming to provide an energetic guide for estimating their trifluoromethyl radical donor abilities. A comprehensive TR^·DA scale was constructed, which covers a range from -21.5 to 95.2 kcal·mol^-1. The effects of the frequently used activators including single electron transfer reagents and halogen/chalcogen-bond donors on trifluoromethyl radical donor abilities were investigated. The results show that single electron transfer is the most efficient way to promote the CF₃ radical release. We expect that the results of this study could be highly valuable for the mechanistic understanding and the rational design of novel CF₃ sources and new radical trifluoromethylation reactions.
- radical trifluoromethylating reagent,
- homolytic bond dissociation enthalpy,
- structure-reactivity relationship,
- halogen bond,
- DFT calculation
1. [1]
  (a) Leo, A.; Hansch, C.; Elkins, D. Chem. Rev. 1971, 71, 525. (b) Hansch, C.; Leo, A.; Unger, S. H.; Kim, K. H.; Nikaitani, D.; Lien, E. J. J. Med. Chem. 1973, 16, 1207. (c) Hansch, C.; Leo, A.; Taft, R. W. Chem. Rev. 1991, 91, 165.
2. [2]
  (a) Müller, K.; Faeh, C.; Diederich, F. Science 2007, 317, 1881. (b) Purser, S.; Moore, P. R.; Swallow, S.; Gouverneur, V. Chem. Soc. Rev. 2008, 37, 320. (c) Zhou, Y.; Wang, J.; Gu, Z.; Wang, S.; Zhu, W.; Ace a, J. L.; Soloshonok, V. A.; Izawa, K.; Liu, H. Chem. Rev. 2016, 116, 422.
3. [3]
  Kirsch, P. Modern Fluoroorganic Chemistry:Synthesis, Reactivity, Applications, Wiley-VCH, Weinheim, Germany, 2013.
4. [4]
  (a) Zhang, C.-P.; Chen, Q.-Y.; Guo, Y.; Xiao, J.-C.; Gu, Y.-C. Chem. Soc. Rev. 2012, 41, 4536. (b) Chu, L.; Qing, F.-L. Acc. Chem. Res. 2014, 47, 1513. (c) Xu, X. H.; Matsuzaki, K.; Shibata, N. Chem. Rev. 2015, 115, 731. (d) Ni, C.; Hu, M.; Hu, J. Chem. Rev. 2015, 115, 765. (e) Liu, X.; Xu, C.; Wang, M.; Liu, Q. Chem. Rev. 2015, 115, 683.
5. [5]
  (a) Wang, X.; Zhang, Y.; Wang, J.-B. Sci. Sin. Chim. 2012, 42, 1417(in Chinese). (王兮, 张艳, 王剑波, 中国科学: 化学, 2012, 42, 1417.) (b) Pan, F.; Shi, Z. Acta Chim. Sinica 2012, 70, 1679. (潘菲, 施章杰, 化学学报, 2012, 70, 1679.) (c) Qing, F.-L. Chin. J. Org. Chem. 2012, 32, 815(in Chinese). (卿凤翎, 有机化学, 2012, 32, 815.) (d) Zeng, W.; Chen F. Chin. J. Appl. Chem. 2014, 31, 627(in Chinese). (曾薇, 陈甫雪, 应用化学, 2014, 31, 627.) (e) Ma, J.-A.; Cahard, D. J. Fluorine Chem. 2007, 128, 975. (f) Hui, R.; Zhang, S.; Tan, Z.; Wu, X.; Feng, B. Chin. J. Org. Chem. 2017, 37, 3060(in Chinese). (惠人杰, 张士伟, 谭政, 吴小培, 冯柏年, 有机化学, 2017, 37, 3060.) (g) Gou, B.; Yang, C.; Zhang, L.; Xia, W. Acta Chim. Sinica 2017, 75, 66(in Chinese). (苟宝权, 杨超, 张磊, 夏吾炯, 化学学报, 2017, 75, 66.) (h) Song, H.-X.; Han, Q.-Y.; Zhao, C.-L.; Zhang, C.-P. Green Chem. 2018, 20, 1662.
6. [6]
  (a) Dolbier, W. R. Chem. Rev. 1996, 96, 1557. (b) Studer, A. Angew. Chem. Int. Ed. 2012, 51, 8950.
7. [7]
  (a) Haszeldine, R. N. J. Chem. Soc. 1949, 2856. (b) Scherer, K. V.; Ono, T.; Yamanouchi, K.; Fernandez, R.; Henderson, P. J. Am. Chem. Soc. 1985, 107, 718. (c) Umemoto, T.; Ando, A. Bull. Chem. Soc. Jpn. 1986, 59, 447. (d) Sawada, H.; Nakayama, M.; Yoshida, M.; Yoshida, T.; Kamigata, N. J. Fluorine Chem. 1990, 46, 423. (e) Langlois, B. R.; Laurent, E.; Roidot, N. Tetrahedron Lett. 1991, 32, 7525. (f) Bertrand, F.; Pevere, V.; Quiclet-Sire, B.; Zard, S. Z. Org. Lett. 2001, 3, 1069. (g) Fujiwara, Y.; Dixon, J. A.; O'Hara, F.; Funder, E. D.; Dixon, D. D.; Rodriguez, R. A.; Baxter, R. D.; Herle, B.; Sach, N.; Collins, M. R.; Ishihara, Y.; Baran, P. S. Nature 2012, 492, 95. (h) Sato, A.; Han, J.; Ono, T.; Wzorek, A.; Acena, J. L.; Soloshonok, V. A. Chem. Commun. 2015, 51, 5967. (i) Rong, J.; Deng, L.; Tan, P.; Ni, C.; Gu, Y.; Hu, J. Angew. Chem. Int. Ed. 2016, 55, 2743. (j) Liu, P.; Liu, W.; Li, C. J. J. Am. Chem. Soc. 2017, 139, 14315. (k) Rong, J.; Ni, C.; Wang, Y.; Kuang, C.; Gu, Y.; Hu, J. Acta Chim. Sinica 2017, 75, 105(in Chinese). (荣健, 倪传法, 王云泽, 匡翠文, 顾玉诚, 胡金波, 化学学报, 2017, 75, 105.) (l) Daniel, M.; Dagousset, G.; Diter, P.; Klein, P. A.; Tuccio, B.; Goncalves, A. M.; Masson, G.; Magnier, E. Angew. Chem. Int. Ed. 2017, 56, 1. (m) Ouyang, Y.; Xu, X. H.; Qing, F. L. Angew. Chem. Int. Ed. 2018, 57, 6926. (n) Yang, B.; Yu, D.; Xu, X.-H.; Qing, F.-L. ACS Catal. 2018, 2839. (o) Liu, Y.; Shao, X.; Zhang, P.; Lu, L.; Shen, Q. Org. Lett. 2015, 17, 2752.
8. [8]
  (a) Chatterjee, T.; Iqbal, N.; You, Y.; Cho, E. J. Acc. Chem. Res. 2016, 49, 2284. (b) Koike, T.; Akita, M. Acc. Chem. Res. 2016, 49, 1937. (c) Cho, E. J. Chem. Rec. 2016, 16, 47. (d) Zeng, T.; Xuan, J.; Chen, J.; Lu, L.; Xiao, W. Imag. Sci. Photochem. 2014, 32, 415(in Chinese). (曾婷婷, 宣俊, 陈加荣, 陆良秋, 肖文精, 影像科学与光化学, 2014, 32, 415.)
9. [9]
  (a) Xu, J.; Liu, X.; Fu, Y. Tetrahedron Lett. 2014, 55, 585. (b) Koike, T.; Akita, M. J. Fluorine Chem. 2014, 167, 30. (c) Wang, S.-M.; Han, J.-B.; Zhang, C.-P.; Qin, H.-L.; Xiao, J.-C. Tetrahedron 2015, 71, 7949. (d) Prieto, A.; Baudoin, O.; Bouyssi, D.; Monteiro, N. Chem. Commun. 2016, 52, 869. (e) Ling, L.; Liu, K.; Li, X.; Li, Y. ACS Catal. 2015, 5, 2458. (f) He, X.; Shan, C.; Qi, X.; Bai, R.; Lan, Y. Sci. Sin. Chim. 2017, 47, 859(in Chinese). (何晓倩, 单春晖, 戚孝天, 白若鹏, 蓝宇, 中国科学: 化学, 2017, 47, 859.) (g) Ye, J.-H.; Zhu, L.; Yan, S.-S.; Miao, M.; Zhang, X.-C.; Zhou, W.-J.; Li, J.; Lan, Y.; Yu, D.-G. ACS Catal. 2017, 7, 8324.; (h) Zhu, L.; Ye, J.-H.; Duan, M.; Qi, X.; Yu, D.-G.; Bai, R.; Lan, Y. Org. Chem. Front. 2018, 5, 633.
10. [10]
  (a) Beale, T. M.; Chudzinski, M. G.; Sarwar, M. G.; Taylor, M. S. Chem. Soc. Rev. 2013, 42, 1667. (b) Cavallo, G.; Metrangolo, P.; Milani, R.; Pilati, T.; Priimagi, A.; Resnati, G.; Terraneo, G. Chem. Rev. 2016, 116, 2478.
11. [11]
  (a) Mulliken, R. S. J. Am. Chem. Soc. 1950, 72, 600. (b) Rosokha, S. V.; Kochi, J. K. Acc. Chem. Res. 2008, 41, 641. (c) Lima, C. G. S.; Lima, T. d. M.; Duarte, M.; Jurberg, I. D.; Paixã o, M. W. ACS Catal. 2016, 6, 1389. (e) Postigo, A. Eur. J. Org. Chem. 2018, https://doi.org/10.1002/ejoc.201801079.
12. [12]
  Sladojevich, F.; McNeill, E.; Börgel, J.; Zheng, S.-L.; Ritter, T. Angew. Chem. Int. Ed. 2015, 54, 3712. doi: 10.1002/anie.201410954
13. [13]
  (a) Sun, X.; Wang, W.; Li, Y.; Ma, J.; Yu, S. Org. Lett. 2016, 18, 4638. (b) Sun, X.; Wang, W.; Ma, J.; Yu, S. Acta Chim. Sinica 2017, 75, 115(in Chinese). (孙晓阳, 王文敏, 马晶, 俞寿云, 化学学报, 2017, 75, 115.) (c) Sun, X.; He, Y.; Yu, S. J. Photochem. Photobiol., A 2018, 355, 326.
14. [14]
  Wang, Y.; Wang, J.; Li, G.-X.; He, G.; Chen, G. Org. Lett. 2017, 19, 1442. doi: 10.1021/acs.orglett.7b00375
15. [15]
  (a) Cheng, Y.; Yu, S. Org. Lett. 2016, 18, 2962. (b) Jiang, H.; He, Y.; Cheng, Y.; Yu, S. Org. Lett. 2017, 19, 1240.
16. [16]
  Cheng, Y.; Yuan, X.; Ma, J.; Yu, S. Chem. Eur. J. 2015, 21, 8355. doi: 10.1002/chem.v21.23
17. [17]
  (a) Jiang, Y. Y.; Yu, H. Z.; Fu, Y.; Liu, L. Sci. China Chem. 2015, 58, 673. (b) Mizuta, S.; Verhoog, S.; Wang, X.; Shibata, N.; Gouverneur, V.; Meciebielle, M. J. Fluorine Chem. 2013, 155, 124. (c) Li, M.; Wang, Y.; Xue, X. S.; Cheng, J. P. Asian J. Org. Chem. 2017, 6, 235.
18. [18]
  (a) Li, M.; Guo, J.; Xue, X. S.; Cheng, J. P. Org. Lett. 2016, 18, 264. (b) Li, M.; Xue, X. S.; Guo, J.; Wang, Y.; Cheng, J. P. J. Org. Chem. 2016, 81, 3119. (c) Xue, X. S.; Wang, Y.; Li, M.; Cheng, J. P. J. Org. Chem. 2016, 81, 4280. (d) Yan, T.; Zhou, B.; Xue, X. S.; Cheng, J. P. J. Org. Chem. 2016, 81, 9006. (e) Zhang, P.; Li, M.; Xue, X.-S.; Xu, C.; Zhao, Q.; Liu, Y.; Wang, H.; Guo, Y.; Lu, L.; Shen, Q. J. Org. Chem 2016, 81, 7486. (f) Zhou, B.; Yan, T.; Xue, X. S.; Cheng, J. P. Org. Lett. 2016, 18, 6128. (g) Li, M.; Xue, X.-S.; Cheng, J.-P. ACS Catal. 2017, 7, 7977. (h) Li, M.; Zhou, B.; Xue, X.-S.; Cheng, J.-P. J. Org. Chem. 2017, 82, 8697. (i) Yang, J. D.; Wang, Y.; Xue, X. S.; Cheng, J. P. J. Org. Chem. 2017, 82, 4129. (j) Zhou, B.; Xue, X. S.; Cheng, J. P. Tetrahedron Lett. 2017, 58, 1287. (k) Li, M.; Sang, Y.; Xue, X.-S.; Cheng, J.-P. J. Org. Chem. 2018, 83, 3333. (l) Li, M.; Zheng, H.; Xue, X.-S.; Cheng, J.-P. Tetrahedron Lett. 2018, 59, 1278. (m) Zhang, J.; Yang, J.-D.; Zheng, H.; Xue, X.-S.; Mayr, H.; Cheng, J.-P. Angew. Chem. Int. Ed. 2018, 57, 12690.
19. [19]
  (a) Zhao, Y.; Truhlar, D. G. Acc. Chem. Res. 2008, 41, 157. (b) Klippenstein, S. J.; Pande, V. S.; Truhlar, D. G. J. Am. Chem. Soc. 2014, 136, 528.
20. [20]
  Marenich, A. V.; Cramer, C. J.; Truhlar, D. G. J. Phys. Chem. B 2009, 113, 6378. doi: 10.1021/jp810292n
21. [21]
  Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Scalmani, G.; Barone, V.; Mennucci, B.; Petersson, G. A.; Nakatsuji, H.; Caricato, M.; Li, X.; Hratchian, H. P.; Izmaylov, A. F.; Bloino, J.; Zheng, G.; Sonnenberg, J. L.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Vreven, T.; Montgomery, J. A.; Jr., J. E. P.; Ogliaro, F.; Bearpark, M.; Heyd, J. J.; Brothers, E.; Kudin, K. N.; Staroverov, V. N.; Keith, T.; Kobayashi, R.; Normand, J.; Raghavachari, K.; Rendell, A.; Burant, J. C.; Iyengar, S. S.; Tomasi, J.; Cossi, M.; Rega, N.; Millam, J. M.; Klene, M.; Knox, J. E.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Martin, R. L.; Morokuma, K.; Zakrzewski, V. G.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Dapprich, S.; Daniels, A. D.; Farkas, O.; Foresman, J. B.; Ortiz, J. V.; Cioslowski, J.; Fox, D. J. Gaussian 09, Revision D. 01, Gaussian, Inc., Wallingford CT, 2013.
22. [22]
  Naumann, D.; Wilkes, B.; Kischkewitz, J. J. Fluorine Chem. 1985, 30, 73. doi: 10.1016/S0022-1139(00)80523-0
23. [23]
  Naumann, D.; Kischkewitz, J. J. Fluorine Chem. 1990, 46, 265. doi: 10.1016/S0022-1139(00)80995-1
24. [24]
  Haszeldine, R. N. J. Chem. Soc. 1949, 2856. doi: 10.1039/jr9490002856
25. [25]
  Stefani, A. P.; Herk, L.; Szwarc, M. J. Am. Chem. Soc. 1961, 83, 4732. doi: 10.1021/ja01484a010
26. [26]
  Akiyama, T.; Kato, K.; Kajitani, M.; Sakaguchi, Y.; Nakamura, J.; Hayashi, H.; Sugimori, A. Bull. Chem. Soc. Jpn. 1988, 61, 3531. doi: 10.1246/bcsj.61.3531
27. [27]
  Sangster, J. M.; Thynne, J. C. J. J. Phys. Chem. 1969, 73, 2746. doi: 10.1021/j100842a049
28. [28]
  Kamigata, N.; Fukushima, T.; Yoshida, M. J. Chem. Soc., Chem. Commun. 1989, 1559.
29. [29]
  Hu, L.-Q.; Huang, W.-Y. Chin. J. Chem. 1989, 9, 498(in Chinese).
30. [30]
  Billard, T.; Roques, N.; Langlois, B. R. J. Org. Chem. 1999, 64, 3813. doi: 10.1021/jo980649a
31. [31]
  Gong, J.; Fuchs, P. L. J. Am. Chem. Soc. 1996, 118, 4486.
32. [32]
  Lai, C.; Mallouk, T. E. J. Chem. Soc., Chem. Commun. 1993, 1359.
33. [33]
  Shi, G.; Shao, C.; Pan, S.; Yu, J.; Zhang, Y. Org. Lett. 2015, 17, 38. doi: 10.1021/ol503189j
34. [34]
  Beatty, J. W.; Douglas, J. J.; Cole, K. P.; Stephenson, C. R. J. Nat. Commun. 2015, 6, 1. doi: 10.1080/0976691X.2015.11884842
35. [35]
  Kawamura, S.; Sodeoka, M. Angew. Chem. Int. Ed. 2016, 55, 8740. doi: 10.1002/anie.201604127
36. [36]
  Billard, T.; Roques, N.; Langlois, B. R. Tetrahedron Lett. 2000, 41, 3069. doi: 10.1016/S0040-4039(00)00337-3
37. [37]
  Umemoto, T. J. Fluorine Chem. 2014, 167, 3. doi: 10.1016/j.jfluchem.2014.07.029
38. [38]
  (a) Gleiter, R.; Haberhauer, G.; Werz, D. B.; Rominger, F.; Bleiholder, C. Chem. Rev. 2018, 118, 2010. (b) Vogel, L.; Wonner, P.; Huber, S. M. Angew. Chem. Int. Ed. 2018, DOI: 10.1002/anie.201809432.
1. [1]
  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
2. [2]
  Rui Li , Jiayu Zhang , Anyang Li . Two Levels of Understanding of Chemical Bonds: a Case of the Bonding Model of Hypervalent Molecules. University Chemistry, 2024, 39(2): 392-398. doi: 10.3866/PKU.DXHX202308051
3. [3]
  Linhan Tian , Changsheng Lu . Discussion on Sextuple Bonding in Diatomic Motifs of Chromium Family Elements. University Chemistry, 2024, 39(8): 395-402. doi: 10.3866/PKU.DXHX202401056
4. [4]
  Jiaqi AN , Yunle LIU , Jianxuan SHANG , Yan GUO , Ce LIU , Fanlong ZENG , Anyang LI , Wenyuan WANG . Reactivity of extremely bulky silylaminogermylene chloride and bonding analysis of a cubic tetragermylene. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1511-1518. doi: 10.11862/CJIC.20240072
5. [5]
  Changqing MIAO , Fengjiao CHEN , Wenyu LI , Shujie WEI , Yuqing YAO , Keyi WANG , Ni WANG , Xiaoyan XIN , Ming FANG . Crystal structures, DNA action, and antibacterial activities of three tetranuclear lanthanide-based complexes. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2455-2465. doi: 10.11862/CJIC.20240192
6. [6]
  Lei Shi . Nucleophilicity and Electrophilicity of Radicals. University Chemistry, 2024, 39(11): 131-135. doi: 10.3866/PKU.DXHX202402018
7. [7]
  Min LIU , Huapeng RUAN , Zhongtao FENG , Xue DONG , Haiyan CUI , Xinping WANG . Neutral boron-containing radical dimers. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 123-130. doi: 10.11862/CJIC.20240362
8. [8]
  Tianqi Bai , Kun Huang , Fachen Liu , Ruochen Shi , Wencai Ren , Songfeng Pei , Peng Gao , Zhongfan Liu . 石墨烯厚膜热扩散系数与微观结构的关系. Acta Physico-Chimica Sinica, 2025, 41(3): 2404024-. doi: 10.3866/PKU.WHXB202404024
9. [9]
  Yanhui Zhong , Ran Wang , Zian Lin . Analysis of Halogenated Quinone Compounds in Environmental Water by Dispersive Solid-Phase Extraction with Liquid Chromatography-Triple Quadrupole Mass Spectrometry. University Chemistry, 2024, 39(11): 296-303. doi: 10.12461/PKU.DXHX202402017
10. [10]
  Qiqi Li , Su Zhang , Yuting Jiang , Linna Zhu , Nannan Guo , Jing Zhang , Yutong Li , Tong Wei , Zhuangjun Fan . 前驱体机械压实制备高密度活性炭及其致密电容储能性能. Acta Physico-Chimica Sinica, 2025, 41(3): 2406009-. doi: 10.3866/PKU.WHXB202406009
11. [11]
  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
12. [12]
  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
13. [13]
  Haitang WANG , Yanni LING , Xiaqing MA , Yuxin CHEN , Rui ZHANG , Keyi WANG , Ying ZHANG , Wenmin WANG . Construction, crystal structures, and biological activities of two Ln^Ⅲ₃ complexes. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1474-1482. doi: 10.11862/CJIC.20240188
14. [14]
  Zitong Chen , Zipei Su , Jiangfeng Qian . Aromatic Alkali Metal Reagents: Structures, Properties and Applications. University Chemistry, 2024, 39(8): 149-162. doi: 10.3866/PKU.DXHX202311054
15. [15]
  Lu XU , Chengyu ZHANG , Wenjuan JI , Haiying YANG , Yunlong FU . Zinc metal-organic framework with high-density free carboxyl oxygen functionalized pore walls for targeted electrochemical sensing of paracetamol. Chinese Journal of Inorganic Chemistry, 2024, 40(5): 907-918. doi: 10.11862/CJIC.20230431
16. [16]
  Zhaoyang WANG , Chun YANG , Yaoyao Song , Na HAN , Xiaomeng LIU , Qinglun WANG . Lanthanide(Ⅲ) complexes derived from 4′-(2-pyridyl)-2, 2′∶6′, 2″-terpyridine: Crystal structures, fluorescent and magnetic properties. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1442-1451. doi: 10.11862/CJIC.20240114
17. [17]
  Shihui Shi , Haoyu Li , Shaojie Han , Yifan Yao , Siqi Liu . Regioselectively Synthesis of Halogenated Arenes via Self-Assembly and Synergistic Catalysis Strategy. University Chemistry, 2024, 39(5): 336-344. doi: 10.3866/PKU.DXHX202312002
18. [18]
  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
19. [19]
  Jing WU , Puzhen HUI , Huilin ZHENG , Pingchuan YUAN , Chunfei WANG , Hui WANG , Xiaoxia GU . Synthesis, crystal structures, and antitumor activities of transition metal complexes incorporating a naphthol-aldehyde Schiff base ligand. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2422-2428. doi: 10.11862/CJIC.20240278
20. [20]
  Liyang ZHANG , Dongdong YANG , Ning LI , Yuanyu YANG , Qi MA . Crystal structures, luminescent properties and Hirshfeld surface analyses of three cadmium(Ⅱ) complexes based on 2-(3-(pyridin-2-yl)-1H-pyrazol-1-yl)benzoate. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1943-1952. doi: 10.11862/CJIC.20240079

Get Citation

PDF

XML

Metrics

PDF Downloads(75)
Abstract views(2277)
HTML views(465)

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

Computational Study of the Trifluoromethyl Radical Donor Abilities of CF3 Sources

Metrics

通讯作者: 陈斌, bchen63@163.com

Computational Study of the Trifluoromethyl Radical Donor Abilities of CF₃ Sources