Citation: Manuel Petroselli, Yong-Qing Chen, Ming-Kai Zhao, Julius Rebek, Yang Yu. C-H···X-C bonds in alkyl halides drive reverse selectivities in confined spaces[J]. Chinese Chemical Letters, ;2023, 34(5): 107834. doi: 10.1016/j.cclet.2022.107834 shu

C-H···X-C bonds in alkyl halides drive reverse selectivities in confined spaces

Manuel Petroselli ^a ,
Yong-Qing Chen ^a ,
Ming-Kai Zhao ^a ,
Julius Rebek ^{a, b} ,
Yang Yu ^{a, *,}

a.
Center for Supramolecular Chemistry and Catalysis and Department of Chemistry, College of Science, Shanghai University, Shanghai 200444, China
b.
Skaggs Institute for Chemical Biology and Department of Chemistry, The Scripps Research Institute, La Jolla, CA 92037, United States

yangyu2017@shu.edu.cn

Received Date: 28 June 2022
Revised Date: 8 September 2022
Accepted Date: 14 September 2022
Available Online: 18 September 2022

Figures(5)

Binding of non-activated alkyl halides (2–20) in water-soluble cavitand (1) through supramolecular forces is here reported, with emphasis on the role of size and polarizability of the halogen atom in the formation of intramolecular C-H hydrogen bonds in confined spaces. Rare reverse affinity in water (RI < RBr < RCl) is surprisingly observed for the more water-soluble short alkyl halides in dynamic open-ended containers. Competitive bindings and theoretical calculations confirm the unusual selectivity and the presence of C-H hydrogen bonds in non-activated systems for the first time, pointing out the importance and effect of subtle forces on molecular recognition in confined spaces.
- Water-soluble cavitand,
- Host-guest complex,
- Molecular recognition,
- C-H hydrogen bond,
- Alkyl halides
1. [1]
  D. Leckband, J. Israelachvili, Q. Rev. Biophys. 34 (2001) 105–267. doi: 10.1017/S0033583501003687
2. [2]
  C.C. Robetson, J.S. Wright, E.J. Carrington, et al., Chem. Sci. 8 (2017) 5392–5398. doi: 10.1039/C7SC01801K
3. [3]
  S. Shoda, H. Uyama, J. Kadokawa, et al., Chem. Rev. 116 (2016) 2307–2413. doi: 10.1021/acs.chemrev.5b00472
4. [4]
  M. Petroselli, V. Angamuthu, F.U. Rahman, et al., J. Am. Chem. Soc. 142 (2020) 2396–2403. doi: 10.1021/jacs.9b11595
5. [5]
  A. Galan, P. Ballester, Chem. Soc. Rev. 45 (2016) 1720–1737. doi: 10.1039/C5CS00861A
6. [6]
  J. Murray, K. Kim, T. Ogoshi, et al., Chem. Soc. Rev. 46 (2017) 2479. doi: 10.1039/C7CS00095B
7. [7]
  D. Ajami, H. Dube, J. Rebek, J. Am. Chem. Soc. 133 (2011) 9689. doi: 10.1021/ja203123k
8. [8]
  V. Ramamurthy, Acc. Chem. Res. 48 (2015) 2904. doi: 10.1021/acs.accounts.5b00360
9. [9]
  P.Y. Lia, Y. Chen, Y. Liu, Chin. Chem. Lett. 30 (2019) 1190–1197. doi: 10.1016/j.cclet.2019.03.035
10. [10]
  S. Niu, L.L. Mao, H.Y. Xiao, et al., Chin. Chem. Lett. 33 (2022) 1970–1974. doi: 10.1016/j.cclet.2021.09.090
11. [11]
  R.J. Hooley, J. Rebek, Chem. Biol. 16 (2009) 255–264. doi: 10.1016/j.chembiol.2008.09.015
12. [12]
  T. Iwasawa, R.J. Hooley, J. Rebek, Science 317 (2007) 493–496. doi: 10.1126/science.1143272
13. [13]
  Q.X. Shi, D. Masseroni, J. Rebek, J. Am. Chem. Soc. 138 (2016) 10846–10848. doi: 10.1021/jacs.6b06950
14. [14]
  N.W. Wu, I.D. Petsalakis, G. Theodorakopoulos, et al., Angew. Chem. Int. Ed. 130 (2018) 15311–15315. doi: 10.1002/ange.201808265
15. [15]
  N.W. Wu, J. Rebek, J. Am. Chem. Soc. 138 (2016) 7512–7515. doi: 10.1021/jacs.6b04278
16. [16]
  S. Mosca, Y. Yu, J.V. Gavette, et al., J. Am. Chem. Soc. 137 (2015) 14582–14585. doi: 10.1021/jacs.5b10028
17. [17]
  V. Angamuthu, F.U. Rahman, M. Petroselli, et al., Org. Chem. Front. 6 (2019) 3220–3223. doi: 10.1039/C9QO00849G
18. [18]
  D. Masseroni, S. Mosca, M.P. Mower, et al., Angew. Chem. Int. Ed. 55 (2016) 8290–8293. doi: 10.1002/anie.201602355
19. [19]
  M. Petroselli, J. Rebek, Y. Yu, Chem. Eur. J. 27 (2021) 3284–3287. doi: 10.1002/chem.202004953
20. [20]
  M. Petroselli, Y.Q. Chen, J. Rebek, G. Synth, Green Synth. Catal. 2 (2021) 123–130. doi: 10.1016/j.gresc.2021.03.004
21. [21]
  M. Rao, W.H. Wu, C. Yang, Green Synth. Catal. 2 (2021) 131–144. doi: 10.1016/j.gresc.2021.03.005
22. [22]
  V. Angamuthu, M. Petroselli, F.U. Rahman, et al., Org. Biomol. Chem. 17 (2019) 5279–5282. doi: 10.1039/C9OB01018A
23. [23]
  H.N. Feng, M. Petroselli, X.H. Zhang, et al., Supramol. Chem. 31 (2019) 108–113. doi: 10.1080/10610278.2018.1564830
24. [24]
  Z.B. Zhang, Y.G. Shao, J.D. Tang, et al., Green Synth. Catal. 2 (2021) 156–164. doi: 10.1016/j.gresc.2021.03.007
25. [25]
  G.P. Sun, M.Z. Zuo, W.R. Qian, et al., Green Synth. Catal. 2 (2021) 32–37. doi: 10.1016/j.gresc.2021.01.003
26. [26]
  Z.R. Laughrey, T.G. Upton, B.C. Gibb, Chem. Commun. (2006) 970–972.
27. [27]
  C.L. Gibb, E.D. Stevens, B.C. Gibb, J. Am. Chem. Soc. 123 (2001) 5849–5850. doi: 10.1021/ja005931p
28. [28]
  K. Kobayashi, K. Ishii, S. Sakamoto, et al., J. Am. Chem. Soc. 125 (2003) 10615–10624. doi: 10.1021/ja035337q
29. [29]
  R.J. Hooley, J.V. Gavette, M. Mettry, et al., Chem. Sci. 5 (2014) 4382–4387. doi: 10.1039/C4SC01316F
30. [30]
  Y. Yu, Y.S. Li, J. Rebek, New J. Chem. 42 (2018) 9945–9948. doi: 10.1039/C8NJ01567H
31. [31]
  F.U. Rahman, Y.S. Li, I.D. Petsalakis, et al., Proc. Natl. Acad. Sci. U. S. A. 116 (2019) 17648–17653. doi: 10.1073/pnas.1909154116
32. [32]
  J.R. Moran, S. Karbach, D.J. Cram, J. Am. Chem. Soc. 104 (1982) 5826–5828. doi: 10.1021/ja00385a064
33. [33]
  Y.Q. Chen, H.W. Guan, K. Kanagaraj, J. Rebeka Jr., Y. Yu, Chin. Chem. Lett. 33 (2022) 4908–4911. doi: 10.1016/j.cclet.2022.03.039
34. [34]
  O. Takahashi, Y. Kohno, M. Nishio, Chem. Rev. 110 (2010) 6049–6076. doi: 10.1021/cr100072x
35. [35]
  C.Z. Liu, S. Koppireddi, H. Wang, Chin. Chem. Lett. 30 (2019) 953–956. doi: 10.1016/j.cclet.2019.02.010
36. [36]
  M. Ikeda, A.K. Sah, M. Iwase, et al., Dalton Trans. 46 (2017) 3800–3804. doi: 10.1039/C6DT03390C
37. [37]
  I. Bandyopadhyay, K. Raghavachari, A.H. Flood, Chem. Phys. Chem. 10 (2009) 2535–2540. doi: 10.1002/cphc.200900476
38. [38]
  B. Nepal, S. Scheiner, Chem. Eur. J. 21 (2015) 1474–1481. doi: 10.1002/chem.201404970
39. [39]
  M. Castro, I. Nicolàs-Vazques, J.I. Zavala, et al., J. Chem. Theory Comput. 3 (2007) 681–688. doi: 10.1021/ct600336r
40. [40]
  O. Takahashi, K. Yamasaki, Y. Kohno, et al., Chem. Phys. Lett. 440 (2007) 64–69. doi: 10.1016/j.cplett.2007.04.013
1. [1]
  Fang-Yuan Chen , Wen-Chao Geng , Kang Cai , Dong-Sheng Guo . Molecular recognition of cyclophanes in water. Chinese Chemical Letters, 2024, 35(5): 109161-. doi: 10.1016/j.cclet.2023.109161
2. [2]
  Qihan Lin , Jiabin Xing , Yue-Yang Liu , Gang Wu , Shi-Jia Liu , Hui Wang , Wei Zhou , Zhan-Ting Li , Dan-Wei Zhang . taBOX: A water-soluble tetraanionic rectangular molecular container for conjugated molecules and taste masking for berberine and palmatine. Chinese Chemical Letters, 2024, 35(5): 109119-. doi: 10.1016/j.cclet.2023.109119
3. [3]
  Cheng-Da Zhao , Huan Yao , Shi-Yao Li , Fangfang Du , Li-Li Wang , Liu-Pan Yang . Amide naphthotubes: Biomimetic macrocycles for selective molecular recognition. Chinese Chemical Letters, 2024, 35(4): 108879-. doi: 10.1016/j.cclet.2023.108879
4. [4]
  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
5. [5]
  Dan Luo , Jinya Tian , Jianqiao Zhou , Xiaodong Chi . Anthracene-bridged "Texas-sized" box for the simultaneous detection and uptake of tryptophan. Chinese Chemical Letters, 2024, 35(9): 109444-. doi: 10.1016/j.cclet.2023.109444
6. [6]
  Jianmei Guo , Yupeng Zhao , Lei Ma , Yongtao Wang . Ultra-long room temperature phosphorescence, intrinsic mechanisms and application based on host-guest doping systems. Chinese Journal of Structural Chemistry, 2024, 43(9): 100335-100335. doi: 10.1016/j.cjsc.2023.100335
7. [7]
  Caihong Mao , Yanfeng He , Xiaohan Wang , Yan Cai , Xiaobo Hu . Synthesis and molecular recognition characteristics of a tetrapodal benzene cage. Chinese Chemical Letters, 2024, 35(8): 109362-. doi: 10.1016/j.cclet.2023.109362
8. [8]
  Zhimin Sun , Xin-Hui Guo , Yue Zhao , Qing-Yu Meng , Li-Juan Xing , He-Lue Sun . Dynamically switchable porphyrin-based molecular tweezer for on−off fullerene recognition. Chinese Chemical Letters, 2024, 35(6): 109162-. doi: 10.1016/j.cclet.2023.109162
9. [9]
  Chuan-Zhi Ni , Ruo-Ming Li , Fang-Qi Zhang , Qu-Ao-Wei Li , Yuan-Yuan Zhu , Jie Zeng , Shuang-Xi Gu . A chiral fluorescent probe for molecular recognition of basic amino acids in solutions and cells. Chinese Chemical Letters, 2024, 35(10): 109862-. doi: 10.1016/j.cclet.2024.109862
10. [10]
  Lixian Fu , Yiyun Tan , Yue Ding , Weixia Qing , Yong Wang . Water–soluble and polarity–sensitive near–infrared fluorescent probe for long–time specific cancer cell membranes imaging and C. Elegans label. Chinese Chemical Letters, 2024, 35(4): 108886-. doi: 10.1016/j.cclet.2023.108886
11. [11]
  Zhen Dai , Linzhi Tan , Yeyu Su , Kerui Zhao , Yushun Tian , Yu Liu , Tao Liu . Site-specific incorporation of reduction-controlled guest amino acids into proteins for cucurbituril recognition. Chinese Chemical Letters, 2024, 35(5): 109121-. doi: 10.1016/j.cclet.2023.109121
12. [12]
  Shulei Hu , Yu Zhang , Xiong Xie , Luhan Li , Kaixian Chen , Hong Liu , Jiang Wang . Rh(Ⅲ)-catalyzed late-stage C-H alkenylation and macrolactamization for the synthesis of cyclic peptides with unique Trp(C7)-alkene crosslinks. Chinese Chemical Letters, 2024, 35(8): 109408-. doi: 10.1016/j.cclet.2023.109408
13. [13]
  Yi Luo , Lin Dong . Multicomponent remote C(sp²)-H bond addition by Ru catalysis: An efficient access to the alkylarylation of 2H-imidazoles. Chinese Chemical Letters, 2024, 35(10): 109648-. doi: 10.1016/j.cclet.2024.109648
14. [14]
  Bingbing Shi , Yuchun Wang , Yi Zhou , Xing-Xing Zhao , Yizhou Li , Nuoqian Yan , Wen-Juan Qu , Qi Lin , Tai-Bao Wei . A supramolecular oligo[2]rotaxane constructed by orthogonal platinum(Ⅱ) metallacycle and pillar[5]arene-based host–guest interactions. Chinese Chemical Letters, 2024, 35(10): 109540-. doi: 10.1016/j.cclet.2024.109540
15. [15]
  Lu LIU , Huijie WANG , Haitong WANG , Ying LI . Crystal structure of a two-dimensional Cd(Ⅱ) complex and its fluorescence recognition of p-nitrophenol, tetracycline, 2, 6-dichloro-4-nitroaniline. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1180-1188. doi: 10.11862/CJIC.20230489
16. [16]
  Haiyang Gu , Xiang Xu . Multicolor hybrid metal halides and anti-counterfeiting. Chinese Journal of Structural Chemistry, 2024, 43(9): 100352-100352. doi: 10.1016/j.cjsc.2024.100352
17. [17]
  Zhenchun Yang , Bixiao Guo , Zhenyu Hu , Kun Wang , Jiahao Cui , Lina Li , Chun Hu , Yubao Zhao . Molecular engineering towards dual surface local polarization sites on poly(heptazine imide) framework for boosting H₂O₂ photo-production. Chinese Chemical Letters, 2024, 35(8): 109251-. doi: 10.1016/j.cclet.2023.109251
18. [18]
  Yongjing Deng , Feiyang Li , Zijian Zhou , Mengzhu Wang , Yongkang Zhu , Jianwei Zhao , Shujuan Liu , Qiang Zhao . Chiral induction and Sb³⁺ doping in indium halides to trigger second harmonic generation and circularly polarized luminescence. Chinese Chemical Letters, 2024, 35(8): 109085-. doi: 10.1016/j.cclet.2023.109085
19. [19]
  Jun-Ting Mo , Zheng Wang . Achieving tunable long persistent luminescence in metal organic halides based on pyridine solvent. Chinese Chemical Letters, 2024, 35(9): 109360-. doi: 10.1016/j.cclet.2023.109360
20. [20]
  Qiongqiong Wan , Yanan Xiao , Guifang Feng , Xin Dong , Wenjing Nie , Ming Gao , Qingtao Meng , Suming Chen . Visible-light-activated aziridination reaction enables simultaneous resolving of C=C bond location and the sn-position isomers in lipids. Chinese Chemical Letters, 2024, 35(4): 108775-. doi: 10.1016/j.cclet.2023.108775

Get Citation

PDF

XML

Metrics

PDF Downloads(3)
Abstract views(426)
HTML views(25)

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