Citation: Shen Yi Shi, Ai Guo Kong, Xin Hua Zhao, Han Ming Ding, Fan Yang, Yong Kui Shan. Nucleophilic substitution of hydrogen in naphthalene by chloride (Cl^-) in ionic liquids[J]. Chinese Chemical Letters, ;2011, 22(2): 147-150. doi: 10.1016/j.cclet.2010.09.021 shu

Nucleophilic substitution of hydrogen in naphthalene by chloride (Cl^-) in ionic liquids

Department of Chemistry, East China Normal University, Shanghai 200062, China

Received Date: 22 July 2010

Fund Project: We thank the key project of Shanghai Science and Technology Committee (Nos. 05JC14070, 06DZ05025, 08JC1408600) for financial supports.

Nucleophilic aromatic substitution of hydrogen in non-activated aromatic ring, a very rare phenomenon in organic chemistry, is found in ionic liquids containing Cl^-as anion under mild reaction conditions. The reaction may be carried out by the addition of the halogen-bonding adduct (Br₂Cl^-) as nucleophile to aromatic ring carbon atom, leading to the formation of the nucleophilic substitution product.
- Ionic liquid,
- Aromatic compound,
- Naphthalene,
- Nucleophilic reaction,
- Halogen bonding
1. [1]
  Tong Zhang , Xiaojing Liang , Licheng Wang , Shuai Wang , Xiaoxiao Liu , Yong Guo . An ionic liquid assisted hydrogel functionalized silica stationary phase for mixed-mode liquid chromatography. Chinese Chemical Letters, 2025, 36(1): 109889-. doi: 10.1016/j.cclet.2024.109889
2. [2]
  Kai An , Qinglong Qiao , Lovelesh , Syed Ali Abbas Abedi , Xiaogang Liu , Zhaochao Xu . "Superimposed" spectral characteristics of fluorophores arising from cross-conjugation hybridization. Chinese Chemical Letters, 2025, 36(1): 109786-. doi: 10.1016/j.cclet.2024.109786
3. [3]
  Boyuan Hu , Jian Zhang , Yulin Yang , Yayu Dong , Jiaqi Wang , Wei Wang , Kaifeng Lin , Debin Xia . Dual-functional POM@IL complex modulate hole transport layer properties and interfacial charge dynamics for highly efficient and stable perovskite solar cells. Chinese Chemical Letters, 2024, 35(7): 108933-. doi: 10.1016/j.cclet.2023.108933
4. [4]
  Jiajia Wang , XinXin Ge , Yajing Xiang , Xiaoliang Qi , Ying Li , Hangbin Xu , Erya Cai , Chaofan Zhang , Yulong Lan , Xiaojing Chen , Yizuo Shi , Zhangping Li , Jianliang Shen . An ionic liquid functionalized sericin hydrogel for drug-resistant bacteria-infected diabetic wound healing. Chinese Chemical Letters, 2025, 36(2): 109819-. doi: 10.1016/j.cclet.2024.109819
5. [5]
  Luyu Zhang , Zirong Dong , Shuai Yu , Guangyue Li , Weiwen Kong , Wenjuan Liu , Haisheng He , Yi Lu , Wei Wu , Jianping Qi . Ionic liquid-based in situ dynamically self-assembled cationic lipid nanocomplexes (CLNs) for enhanced intranasal siRNA delivery. Chinese Chemical Letters, 2024, 35(7): 109101-. doi: 10.1016/j.cclet.2023.109101
6. [6]
  Yan XU , Suzhi LI , Yan LI , Lushun FENG , Wentao SUN , Xinxing LI . Structure variation of cadmium naphthalene-diphosphonates with the changing rigidity of N-donor auxiliary ligands. Chinese Journal of Inorganic Chemistry, 2025, 41(2): 395-406. doi: 10.11862/CJIC.20240226
7. [7]
  Cheng-Yan Wu , Yi-Nan Gao , Zi-Han Zhang , Rui Liu , Quan Tang , Zhong-Lin Lu . Enhancing self-assembly efficiency of macrocyclic compound into nanotubes by introducing double peptide linkages. Chinese Chemical Letters, 2024, 35(11): 109649-. doi: 10.1016/j.cclet.2024.109649
8. [8]
  Xiao-Tong Sun , Hao-Fei Ni , Yi Zhang , Da-Wei Fu . Hybrid perovskite shows temperature-dependent photoluminescence and dielectric response triggered by halogen substitution. Chinese Journal of Structural Chemistry, 2024, 43(6): 100212-100212. doi: 10.1016/j.cjsc.2024.100212
9. [9]
  Lihua Gao , Yinglei Han , Chensheng Lin , Huikang Jiang , Guang Peng , Guangsai Yang , Jindong Chen , Ning Ye . Halogen-assisted octet binding electrons construction of pnictogens towards wide-bandgap nonlinear optical pnictides. Chinese Chemical Letters, 2024, 35(12): 109529-. doi: 10.1016/j.cclet.2024.109529
10. [10]
  Zhenyang Lin . A classification scheme for inorganic cluster compounds based on their electronic structures and bonding characteristics. Chinese Journal of Structural Chemistry, 2024, 43(5): 100254-100254. doi: 10.1016/j.cjsc.2024.100254
11. [11]
  Xu-Hui Yue , Xiang-Wen Zhang , Hui-Min He , Lei Qiao , Zhong-Ming Sun . Synthesis, chemical bonding and reactivity of new medium-sized polyarsenides. Chinese Chemical Letters, 2024, 35(7): 108907-. doi: 10.1016/j.cclet.2023.108907
12. [12]
  Yixia Zhang , Caili Xue , Yunpeng Zhang , Qi Zhang , Kai Zhang , Yulin Liu , Zhaohui Shan , Wu Qiu , Gang Chen , Na Li , Hulin Zhang , Jiang Zhao , Da-Peng Yang . Cocktail effect of ionic patch driven by triboelectric nanogenerator for diabetic wound healing. Chinese Chemical Letters, 2024, 35(8): 109196-. doi: 10.1016/j.cclet.2023.109196
13. [13]
  Pei Cao , Yilan Wang , Lejian Yu , Miao Wang , Liming Zhao , Xu Hou . Dynamic asymmetric mechanical responsive carbon nanotube fiber for ionic logic gate. Chinese Chemical Letters, 2024, 35(6): 109421-. doi: 10.1016/j.cclet.2023.109421
14. [14]
  Qiangwei Wang , Huijiao Liu , Mengjie Wang , Haojie Zhang , Jianda Xie , Xuanwei Hu , Shiming Zhou , Weitai Wu . Observation of high ionic conductivity of polyelectrolyte microgels in salt-free solutions. Chinese Chemical Letters, 2024, 35(4): 108743-. doi: 10.1016/j.cclet.2023.108743
15. [15]
  Hao-Cong Li , Ming Zhang , Qiyan Lv , Kai Sun , Xiao-Lan Chen , Lingbo Qu , Bing Yu . Homogeneous catalysis and heterogeneous separation: Ionic liquids as recyclable photocatalysts for hydroacylation of olefins. Chinese Chemical Letters, 2025, 36(2): 110579-. doi: 10.1016/j.cclet.2024.110579
16. [16]
  Yuanjiao Liu , Xiaoyang Zhao , Songyao Zhang , Yi Wang , Yutuo Zheng , Xinrui Miao , Wenli Deng . Site-selection and recognition of aromatic carboxylic acid in response to coronene and pyridine derivative. Chinese Chemical Letters, 2024, 35(8): 109404-. doi: 10.1016/j.cclet.2023.109404
17. [17]
  Hong Zhang , Cui-Ping Li , Li-Li Wang , Zhuo-Da Zhou , Wen-Sen Li , Ling-Yi Kong , Ming-Hua Yang . Asperochones A and B, two antimicrobial aromatic polyketides from the endophytic fungus Aspergillus sp. MMC-2. Chinese Chemical Letters, 2024, 35(9): 109351-. doi: 10.1016/j.cclet.2023.109351
18. [18]
  Dongying Fu , Lin Pan , Yanli Ma , Yue Zhang . Bilayered Dion–Jacobson lead-iodine hybrid perovskite with aromatic spacer for broadband photodetection. Chinese Chemical Letters, 2025, 36(2): 109621-. doi: 10.1016/j.cclet.2024.109621
19. [19]
  Jun-Ming Cao , Kai-Yang Zhang , Jia-Lin Yang , Zhen-Yi Gu , Xing-Long Wu . Differential bonding behaviors of sodium/potassium-ion storage in sawdust waste carbon derivatives. Chinese Chemical Letters, 2024, 35(4): 109304-. doi: 10.1016/j.cclet.2023.109304
20. [20]
  Meng Shan , Yongmei Yu , Mengli Sun , Shuping Yang , Mengqi Wang , Bo Zhu , Junbiao Chang . Bifunctional organocatalyst-catalyzed dynamic kinetic resolution of hemiketals for synthesis of chiral ketals via hydrogen bonding control. Chinese Chemical Letters, 2025, 36(1): 109781-. doi: 10.1016/j.cclet.2024.109781