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]
  Long Qin , Peng-Fei Duan , Ming-Hua Liu . Interfacial assembly and host-guest interaction of anthracene-conjugated L-glutamate dendron with cyclodextrin at the air/water interface. Chinese Chemical Letters, 2014, 25(4): 487-490. doi: 10.1016/j.cclet.2013.12.019
2. [2]
  Bai Lin-Ming , Yao Huan , Yang Liu-Pan , Zhang Wen , Jiang Wei . Molecular recognition and fluorescent sensing of urethane in water. Chinese Chemical Letters, 2019, 30(4): 881-884. doi: 10.1016/j.cclet.2018.11.033
3. [3]
  Huang Guo-Bao , Liu Wei-Er , Valkonen Arto , Yao Huan , Rissanen Kari , Jiang Wei . Selective recognition of aromatic hydrocarbons by endo-functionalized molecular tubes via C/N-H… π interactions. Chinese Chemical Letters, 2018, 29(1): 91-94. doi: 10.1016/j.cclet.2017.07.005
4. [4]
  Zhi Gang Zhao , Xing Li Liu , Yi Zhong . Design and synthesis of novel chiral molecular tweezers based on deoxycholic acid. Chinese Chemical Letters, 2008, 19(9): 1051-1054. doi: 10.1016/j.cclet.2008.06.015
5. [5]
  Xiao Xiang Zhao , Zhi Gang Zhao , Xing Li Liu , Xiu Ming Wu . Rapid and efficient synthesis of new chiral aromatic amide molecular tweezers under solvent-free conditions using microwave. Chinese Chemical Letters, 2009, 20(4): 397-400. doi: 10.1016/j.cclet.2008.11.023
6. [6]
  Yuchao Li , Xuezhao Li , Lili Li , Bing Xiao , Jinguo Wu , Hechuan Li , Danyang Li , Cheng He . Phenoxazine-based supramolecular tetrahedron as biomimetic lectin for glucosamine recognition. Chinese Chemical Letters, 2021, 32(2): 735-739. doi: 10.1016/j.cclet.2020.07.028
7. [7]
  Liu Zhuo , Long Jin , Xiao Xuan , Lin Jin-Hong , Zheng Xing , Xiao Ji-Chang , Cao Yu-Cai . Ph₃P⁺CF₂CO₂^- as an F^- and: CF₂ source for trifluoromethylthiolation of alkyl halides. Chinese Chemical Letters, 2019, 30(3): 714-716. doi: 10.1016/j.cclet.2018.11.013
8. [8]
  Xiao-Shi Hu , Hong-Mei Deng , Jian Li , Xue-Shun Jia , Chun-Ju Li . Selective binding of unsaturated aliphatic hydrocarbons by a pillar[5]arene. Chinese Chemical Letters, 2013, 24(8): 707-709.
9. [9]
  Yong-Qing Chen , Hua-Wei Guan , Kuppusamy Kanagaraj , Julius Rebek , Yang Yu . Metal coordination to a deep cavitand promotes binding selectivities in water. Chinese Chemical Letters, 2022, 33(11): 4908-4911. doi: 10.1016/j.cclet.2022.03.039
10. [10]
  Sha-Sha Zhai , Yong Chen , Yu Liu . Selective binding of bile salts by β-cyclodextrin derivatives with appended quinolyl arms. Chinese Chemical Letters, 2013, 24(6): 442-446.
11. [11]
  Xue Zhang , Xiaoyang Wang , Bin Wang , Zhi-Jun Ding , Chunju Li . Carbon-carbon double bond in pillar[5]arene cavity: Selective binding of cis/trans-olefin isomers. Chinese Chemical Letters, 2020, 31(12): 3230-3232. doi: 10.1016/j.cclet.2020.02.037
12. [12]
  Pan Yu-Chen , Tian Han-Wen , Peng Shu , Hu Xin-Yue , Guo Dong-Sheng . Molecular recognition of sulfonatocalixarene with organic cations at the self-assembled interface: a thermodynamic investigation. Chinese Chemical Letters, 2017, 28(4): 787-792. doi: 10.1016/j.cclet.2016.12.027
13. [13]
  Lin Wei , Cen Tian-Yong , Wang Shu-Ping , Zhang Zibin , Wu Jing , Huang Jianying , Li Shijun . Anion recognition with porphyrin-bottomed tetraurea receptors. Chinese Chemical Letters, 2018, 29(9): 1372-1374. doi: 10.1016/j.cclet.2017.10.029
14. [14]
  Li Xuedong , Chen Bo , Lan Ling , Wang Ruili , Luo Duqiang , Liu Li , Cheng Liang . Selective recognition of HIV RNA by dinuclear metallic ligands. Chinese Chemical Letters, 2018, 29(11): 1637-1640. doi: 10.1016/j.cclet.2018.06.003
15. [15]
  Weier Liu , Linghui Kong , Mao Quan , Huan Yao , Liupan Yang , Ho Yu Au-Yeung , Wei Jiang . Selective recognition of methyl viologen by an endo-functionalized naphthobox. Chinese Chemical Letters, 2022, 33(11): 4896-4899. doi: 10.1016/j.cclet.2022.02.076
16. [16]
  Zhang Zibin , Sun Kechang , Li Shijun , Yu Guocan . A pillar[5]arene-based molecular grapple of hexafluorophosphate. Chinese Chemical Letters, 2019, 30(5): 957-960. doi: 10.1016/j.cclet.2019.01.018
17. [17]
  Jing Zhou , Shengzhen Hou , Jin Zhang , Yanru Chen , Hao Chen , Yebang Tan . Fluorescence enhancement and cytotoxicity reduction of bis-viologen biphenyl by complexation of cucurbit[7]uril. Chinese Chemical Letters, 2021, 32(2): 725-728. doi: 10.1016/j.cclet.2020.07.039
18. [18]
  Yang Xiran , Liu Fengbo , Zhao Zhiyong , Liang Feng , Zhang Haijun , Liu Simin . Cucurbit[10]uril-based chemistry. Chinese Chemical Letters, 2018, 29(11): 1560-1566. doi: 10.1016/j.cclet.2018.01.032
19. [19]
  Zhao Hong , Yang Xiao-Hua , Pan Yu-Chen , Tian Han-Wen , Hu Xin-Yue , Guo Dong-Sheng . Inhibition of insulin fibrillation by amphiphilic sulfonatocalixarene. Chinese Chemical Letters, 2020, 31(7): 1873-1876. doi: 10.1016/j.cclet.2020.01.042
20. [20]
  Chen Yanmei , Sun Siyu , Lu Dou , Shi Yujun , Yao Yong . Water-soluble supramolecular polymers constructed by macrocycle-based host-guest interactions. Chinese Chemical Letters, 2019, 30(1): 37-43. doi: 10.1016/j.cclet.2018.10.022

Get Citation

PDF

XML

Metrics

PDF Downloads(2)
Abstract views(119)
HTML views(13)

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