Citation: Zhiwei Wu, Weilu Ding, Yaqin Zhang, Yanlei Wang, Hongyan He. Interaction and Mechanism between Imidazolium Ionic Liquids and the Zwitterionic Amino Acid Tyr: a DFT Study[J]. Acta Physico-Chimica Sinica, ;2021, 37(10): 200202. doi: 10.3866/PKU.WHXB202002021 shu

Interaction and Mechanism between Imidazolium Ionic Liquids and the Zwitterionic Amino Acid Tyr: a DFT Study

Zhiwei Wu ^{1, 2} ,
Weilu Ding ¹ ,
Yaqin Zhang ¹ ,
Yanlei Wang ¹ ,
Hongyan He ^{1, 3,,}

1.
Beijing Key Laboratory of Ionic Liquids Clean Process, Institute of Process Engineering, Chinese Academy of Sciences, Beijing 100190, China
2.
Sino-Danish College, University of Chinese Academy of Sciences, Beijing 100049, China
3.
Zhengzhou Institute of Emerging Industrial Technology, Zhengzhou 450000, China

Corresponding author: Hongyan He, hyhe@ipe.ac.cn
Received Date: 19 February 2020
Revised Date: 21 March 2020
Accepted Date: 6 April 2020
Available Online: 10 April 2020
Fund Project: the National Science Fund for Excellent Young Scholars, China 21922813Key Program of National Natural Science Foundation of China 21834006General program of National Natural Science Foundation of China 21978027Key Research Program of Frontier Sciences of CAS QYZDB-SSW-SLH022Youth Innovation Promotion Association of CAS 2017066

Ionic liquids (ILs) are thermally and chemically stable and have adjustable structures, which gives them the potential to be used as green, efficient biomolecular solvents. Given the critical role of ILs in dissolving biomolecules, the mechanism of interaction between them deserves further study. Herein, density functional theory (DFT) calculations, using the SMD implicit water solvent model, were employed to study the interaction and mechanism between a hydrophobic zwitterionic amino acid (Tyr) and a series of imidazolium ILs with different alkyl chain lengths and methylation sites. The contributions of hydrogen bonding (H-bonding), electrostatic effects, induction, and dispersion to the intermolecular interactions were determined by combining the symmetry-adapted perturbation theory (SAPT), the atoms in molecules (AIM) theory, and reduced density gradient (RDG) analysis. The results indicate that the H-bonding between the IL cation and Tyr is stronger than that between the IL anion and Tyr; however, the binding between either ion and Tyr is dominated by electrostatic effects. By contrast, the difference between the induction and dispersion forces is small when methylation occurs on the C2 site of the imidazolium cation; whereas, it is significantly large when methylation takes place on the N3 site. This is rationalized by the interaction patterns that vary based on the methylation site. H-bonding and π⁺-π stacking interactions between the imidazole and benzene rings are dominant during C2-methylation, while H-bonding and C_Alkyl-H…π interactions between the alkyl chain and benzene ring are dominant during N3-methylation. Increasing the side alkyl chain length has different effects on the interaction energy to cations with different methylation sites. During N3-methylation, when the side alkyl chain length increases from 4 to 12, there are significant van der Waals interactions between the Tyr benzene and the side alkyl chain. However, these van der Waals interactions are inapparent when methylation takes place on the C2 site. Finally, the synergetic effect of the H-bonding and the interaction between the benzene and the side alkyl chain for C2-methylation is greater than the H-bonding and the interaction between the imidazole and benzene rings for N3-methylation, when the side alkyl chain length n > 9. Therefore, the interaction strength and mechanism in these imidazolium-Tyr complexes can be regulated by changing the methylation site and the side alkyl chain length of the cation. Further study of ion-pair and Tyr reveals that the change tendency of the interaction energy of IL-Tyr systems is consistent with that of cation-Tyr cases, and the ion pair further stabilizes the binding with Tyr. These results illustrate the interaction mechanism of IL-Tyr systems and provide a novel strategy for the design and screening of functional ILs for amino acid extraction and separation in the future.
- Ionic liquids,
- Zwitterionic amino acid,
- Interaction and mechanism,
- Hydrogen bond effect,
- Van der Waals effect
1. [1]
  Dong, K.; Liu, X. M.; Dong, H. F.; Zhang, X. P.; Zhang, S. J. Chem. Rev. 2017, 117, 6636. doi: 10.1021/acs.chemrev.6b00776 doi: 10.1021/acs.chemrev.6b00776
2. [2]
  Berthod, A.; Ruiz-Ángel, M. J.; Carda-Broch, S. J. Chromatogr. A 2018, 1559, 2. doi: 10.1016/j.chroma.2017.09.044 doi: 10.1016/j.chroma.2017.09.044
3. [3]
  Rogers, R. D.; Seddon, K. R. Science 2003, 302, 792. doi: 10.1126/science.1090313 doi: 10.1126/science.1090313
4. [4]
  Wei, J.; Dong, H. X.; Chen, X.; Yang, Y. X.; Fang, D. W.; Guan, W.; Yang, J. Z. Acta Phys. -Chim. Sin. 2018, 34, 927. doi: 10.3866/PKU.WHXB201801112
5. [5]
  Caminiti, R.; Gontrani, L. The Structure of Ionic Liquids; Springer: Cham, Switzerland; 2013, pp. 127-148.
6. [6]
  Zhang, S. J.; Wang, J. J.; Lu, X. M.; Zhou, Q. Structures and Interactions of Ionic Liquids; Springer: Berlin, Germany; 2013, pp. 1-38.
7. [7]
  Wang, B. S.; Qin, L.; Mu, T. C.; Xue, Z. M.; Gao, G. H. Chem. Rev. 2017, 117, 7113. doi: 10.1021/acs.chemrev.6b00594 doi: 10.1021/acs.chemrev.6b00594
8. [8]
  Chen, Y.; Mu, T. C. Green Energy Environ. 2019, 4, 95. doi: 10.1016/j.gee.2019.01.012 doi: 10.1016/j.gee.2019.01.012
9. [9]
  Zhao, Q.; Chu, H. W.; Zhao, B. F.; Liang, Z.; Zhang, L. H.; Zhang, Y. K. Trac-Trend. Anal. Chem. 2018, 108, 239. doi: 10.1016/j.trac.2018.09.008 doi: 10.1016/j.trac.2018.09.008
10. [10]
  Kumar, A.; Venkatesu, P. Biophys. Rev. 2018, 10, 841. doi: 10.1007/s12551-018-0411-x doi: 10.1007/s12551-018-0411-x
11. [11]
  Tome, L. I.; Jorge, M.; Gomes, J. R.; Coutinho, J. A. J. Phys. Chem. B 2012, 116, 1831. doi: 10.1021/jp209625e doi: 10.1021/jp209625e
12. [12]
  Yang, H. P.; Chen, L.; Zhou, C. S.; Yu, X. J.; Yagoub, A. E. A.; Ma, H. L. Food Chem. 2018, 245, 346. doi: 10.1016/j.foodchem.2017.10.110 doi: 10.1016/j.foodchem.2017.10.110
13. [13]
  Pei, Y. C.; Li, L.; Li, Z. Y.; Wu, C. Z.; Wang, J. J. Sep. Sci. Technol. 2012, 47, 277. doi: 10.1080/01496395.2011.609241 doi: 10.1080/01496395.2011.609241
14. [14]
  Fang, F.; Zhao, Q.; Li, X.; Liang, Z.; Zhang, L. H.; Zhang, Y. Q. Anal. Chim. Acta 2016, 945, 39. doi: 10.1016/j.aca.2016.09.032 doi: 10.1016/j.aca.2016.09.032
15. [15]
  Schröder, C. Top. Curr. Chem. 2017, 375, 25. doi: 10.1007/s41061-017-0110-2 doi: 10.1007/s41061-017-0110-2
16. [16]
  Kumar, A.; Bisht, M.; Venkatesu, P. Int. J. Biol. Macromol. 2017, 96, 611. doi: 10.1016/j.ijbiomac.2016.12.005 doi: 10.1016/j.ijbiomac.2016.12.005
17. [17]
  Hunt, P. A. Top. Curr. Chem. 2017, 375, 59. doi: 10.1007/s41061-017-0142-7 doi: 10.1007/s41061-017-0142-7
18. [18]
  Scheiner, S.; Kar, T.; Gu, Y. J. Biol. Chem. 2001, 276, 9832. doi: 10.1074/jbc.M010770200 doi: 10.1074/jbc.M010770200
19. [19]
  Dong, K.; Zhang, S. J. Chem. -Eur. J. 2012, 18, 2748. doi: 10.1002/chem.201101645 doi: 10.1002/chem.201101645
20. [20]
  Kim, H. S.; Ha, S. H.; Sethaphong, L.; Koo, Y. M.; Yingling, Y. G. Phys. Chem. Chem. Phys. 2014, 16, 2944. doi: 10.1039/C3CP52516C doi: 10.1039/C3CP52516C
21. [21]
  Yan, H.; Wu, J. Y.; Dai, G. L.; Zhong, A. G.; Chen, H.; Yang, J. G.; Han, D. M. J. Lumin. 2012, 132, 622. doi: 10.1016/j.jlumin.2011.10.026 doi: 10.1016/j.jlumin.2011.10.026
22. [22]
  Nandi, S.; Parui, S.; Halder, R.; Jana, B.; Bhattacharyya, K. Biophys. Rev. 2018, 10, 757. doi: 10.1007/s12551-017-0331-1 doi: 10.1007/s12551-017-0331-1
23. [23]
  Bai, S.; Chang, Y.; Liu, X. J.; Liu, F. F. Acta Phys. -Chim. Sin. 2014, 30, 1239. doi: 10.3866/PKU.WHXB201405151
24. [24]
  Kumar, A.; Bisht, M.; Venkatesu, P. RSC Adv. 2016, 6, 18763. doi: 10.1039/c5ra26690d doi: 10.1039/c5ra26690d
25. [25]
  Klähn, M.; Lim, G. S.; Seduraman, A.; Wu, P. Phys. Chem. Chem. Phys. 2011, 13, 1649. doi: 10.1039/c0cp01509a doi: 10.1039/c0cp01509a
26. [26]
  Mendonca, C. M. N.; Balogh, D. T.; Barbosa, S. C.; Sintra, T. E.; Ventura, S. P. M.; Martins, L. F. G.; Morgado, P.; Filipe, E. J. M.; Coutinho, J. A. P.; Oliveira, O. N.; et al. Phys. Chem. Chem. Phys. 2018, 20, 29764. doi: 10.1039/c8cp05035j doi: 10.1039/c8cp05035j
27. [27]
  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.; et al. Gaussian 09, Revision D. 01; Gaussian Inc.; Wallingford, CT, USA, 2013.
28. [28]
  Gill, P. M. W.; Johnson, B. G.; Pople, J. A.; Frisch, M. Chem. Phys. Lett. 1992, 197, 499. doi: 10.1016/0009-2614(92)85807-M doi: 10.1016/0009-2614(92)85807-M
29. [29]
  Zhao, Y.; Truhlar, D. G. Theor. Chem. Acc. 2008, 120, 215. doi: 10.1007/s00214-007-0310-x doi: 10.1007/s00214-007-0310-x
30. [30]
  Grimme, S.; Antony, J.; Ehrlich, S.; Krieg, H. J. Chem. Phys. 2010, 132, 154104. doi: 10.1063/1.3382344 doi: 10.1063/1.3382344
31. [31]
  Marenich, A. V.; Cramer, C. J.; Truhlar, D. G. J. Phys. Chem. B 2009, 113, 6378. doi: 10.1021/jp810292n doi: 10.1021/jp810292n
32. [32]
  Kessler, J.; Jakubek, M.; Dolenský, B.; Bouř, P. J. Comput. Chem. 2012, 33, 2310. doi: 10.1002/jcc.23063 doi: 10.1002/jcc.23063
33. [33]
  Jeziorski, B.; Moszynski, R.; Szalewicz, K. Chem. Rev. 1994, 94, 1887. doi: 10.1021/cr00031a008 doi: 10.1021/cr00031a008
34. [34]
  Parrish, R. M.; Burns, L. A.; Smith, D. G. A.; Simmonett, A. C.; DePrince, A. E.; Hohenstein, E. G.; Bozkaya, U.; Sokolov, A. Y.; Di Remigio, R.; Richard, R. M.; et al. J. Chem. Theory Comput. 2017, 13, 3185. doi: 10.1021/acs.jctc.7b00174 doi: 10.1021/acs.jctc.7b00174
35. [35]
  Saleh, G.; Gatti, C.; Presti, L. Comput. Theor. Chem. 2012, 998, 148. doi: 10.1016/j.comptc.2012.07.014 doi: 10.1016/j.comptc.2012.07.014
36. [36]
  Johnson, E. R.; Keinan, S.; Mori-Sánchez, P; Contreras-García, J.; Cohen, A. J.; Yang, W. T. J. Am. Chem. Soc. 2010, 132, 6498. doi: 10.1021/ja100936w doi: 10.1021/ja100936w
37. [37]
  Lu, T.; Chen, F. W. J. Comput. Chem. 2012, 33, 580. doi: 10.1002/jcc.22885 doi: 10.1002/jcc.22885
38. [38]
  Heßelmann, A.; Jansen, G. Phys. Chem. Chem. Phys. 2003, 5, 5010. doi: 10.1039/B310529F doi: 10.1039/B310529F
39. [39]
  Hohenstein, E. G.; Sherrill, C. D. Wiley Interdiscip. Rev.: Comput. Mol. Sci. 2012, 2, 304. doi: 10.1002/wcms.84 doi: 10.1002/wcms.84
40. [40]
  Emamian, S.; Lu, T.; Kruse, H.; Emamian, H. J. Comput. Chem. 2019, 40, 2868. doi: 10.1002/jcc.26068 doi: 10.1002/jcc.26068
41. [41]
  Cremer, D.; Kraka, E. Angew. Chem., Int. Ed. Engl. 1984, 23, 627. doi: 10.1002/anie.198406271 doi: 10.1002/anie.198406271
42. [42]
  Bader, R. F. W.; Beddall, P. M. J. Chem. Phys. 1972, 56, 3320. doi: 10.1063/1.1677699 doi: 10.1063/1.1677699
43. [43]
  Zhang, Y. Q.; He, H. Y.; Dong, K.; Fan, M. H.; Zhang, S. J. RSC Adv. 2017, 7, 12670. doi: 10.1039/c6ra27059j doi: 10.1039/c6ra27059j
44. [44]
  He, H. Y.; Zhang, S. J.; Liu, X. M.; Wang, J. Q.; Yao, X. Q.; Zhang, X. P. Fluid Phase Equilib. 2013, 360, 169. doi: 10.1016/j.fluid.2013.09.007 doi: 10.1016/j.fluid.2013.09.007
45. [45]
  Rao, S. S.; Gejji, S. P. J. Phys. Chem. A 2016, 120, 5665. doi: 10.1021/acs.jpca.6b03985 doi: 10.1021/acs.jpca.6b03985
46. [46]
  Matthews, R. P.; Welton, T.; Hunt, P. A. Phys. Chem. Chem. Phys. 2014, 16, 3238. doi: 10.1039/c3cp54672a doi: 10.1039/c3cp54672a
47. [47]
  Ju, Z. Y.; Yao, X. Q.; Luo, Z. F.; Cao, M. J.; Xiao, W. H. Carbohydr. Res. 2020, 487, 107882. doi: 10.1016/j.carres.2019.107882 doi: 10.1016/j.carres.2019.107882
1. [1]
  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
2. [2]
  Xiuyan Li , Chongjiang Wang , Xiwu Zhang , Chengcheng Zhao , Zhihui Yang , Yi Lu , Yifan Cai , Huiping Lu , Hailong Yuan , Wei Wu , Yikang Dai . Enhanced permeation of berberine by ionic liquids for the treatment of posterior age-related macular degeneration following topical delivery. Chinese Chemical Letters, 2026, 37(7): 111714-. doi: 10.1016/j.cclet.2025.111714
3. [3]
  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
4. [4]
  Mengyu Chen , Qinglin Zhou , Tianyun Qin , Ningyao Sun , Yuxi Chen , Yuwei Gong , Xingyi Li , Jinsong Liu . An ionic liquid-reinforced gelatin hydrogel with strong adhesion, antibacterial and anti-inflammatory properties for treating oral ulcers. Chinese Chemical Letters, 2025, 36(7): 110441-. doi: 10.1016/j.cclet.2024.110441
5. [5]
  Mu-Xuan Wu , Li-Ling Su , Shu-Yu Sun , Chen-Xi Bi , Zhao Zheng , Wen-Jun Feng , Bo-Quan Li , Xue-Qiang Zhang , Jia-Qi Huang . Improving the uniformity of lithium deposition via ionic liquid additives for long-cycling lithium–sulfur batteries. Chinese Chemical Letters, 2026, 37(7): 111330-. doi: 10.1016/j.cclet.2025.111330
6. [6]
  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
7. [7]
  Yidan Mao , Bingyu Li , Shuailing Ma , Siwen Cui , Zihan Zhang , Pinwen Zhu , Kongsheng Qi , Xiaodong Li , Weiwei Dong , Wei Luo , Rajeev Ahuja , Dexin Yang , Tian Cui . Metal diborides as robust and highly stable electrodes for efficient electrocatalytic reduction of CO₂ to CO in ionic liquid-based electrolytes. Chinese Chemical Letters, 2026, 37(4): 111675-. doi: 10.1016/j.cclet.2025.111675
8. [8]
  Yun Wang , Huage Lin , Jiaxiang Zong , Mengjiao Yu , Guangyu Wu , Weinan Xing . Interface design of S-scheme Co9S8/flower-like g-C3N4 van der Waals heterojunction with enhanced photocatalytic hydrogen production and tetracycline hydrochloride degradation. Chinese Journal of Structural Chemistry, 2026, 45(2): 100798-100798. doi: 10.1016/j.cjsc.2025.100798
9. [9]
  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
10. [10]
  Qiang Luo , Jinfeng Sun , Zhibo Li , Bin Liu , Jianxun Ding . Thermo-sensitive poly(amino acid) hydrogel mediates cytoprotection through an antioxidant mechanism. Chinese Chemical Letters, 2025, 36(7): 110433-. doi: 10.1016/j.cclet.2024.110433
11. [11]
  Yuan Dong , Mutian Ma , Zhenyang Jiao , Sheng Han , Likun Xiong , Zhao Deng , Yang Peng . Effect of electrolyte cation-mediated mechanism on electrocatalytic carbon dioxide reduction. Chinese Chemical Letters, 2024, 35(7): 109049-. doi: 10.1016/j.cclet.2023.109049
12. [12]
  Qiang Zhang , Yuanbiao Huang , Rong Cao . Imidazolium-Based Materials for CO₂ Electroreduction. Acta Physico-Chimica Sinica, 2024, 40(4): 2306040-0. doi: 10.3866/PKU.WHXB202306040
13. [13]
  Ping Zhang , Hongyuan Ren , Zhaofeng Sun , Hou-Ji Cao , Deshuang Tu , Chang-Sheng Lu , Jordi Poater , Miquel Solà , Hong Yan . Facile and regioselective B–H bond functionalization of carboranes via cage···Ⅰ(Ⅲ) interaction. Chinese Chemical Letters, 2026, 37(5): 111617-. doi: 10.1016/j.cclet.2025.111617
14. [14]
  Yuxin LIAO , Xianheng SHEN , Li CHEN , Yujia TIAN , Zhihong LUO , Xiaoli CHEN , Jiaojing SHAO . Amino-modified F-containing silica slag for the construction of multi-functional interlayer and the inhibitory effect on the polysulfide shuttle effect in lithium-sulfur batteries. Chinese Journal of Inorganic Chemistry, 2026, 42(2): 375-386. doi: 10.11862/CJIC.20250213
15. [15]
  Zhen Liu , Xinyi Xu , Jinkai He , Fei Xu , Qian Li . Revealing the synergistic effect of materials composition and pollutants structure on catalytic degradation mechanism in heterogeneous iron-based Fenton-like reactions. Chinese Chemical Letters, 2026, 37(4): 111644-. doi: 10.1016/j.cclet.2025.111644
16. [16]
  Haiyang Liao , Tiemin Xiao , Tengfei Zhang , Chiam Wen Liew , Xiaofei Duan , Jiayi Su , Hongjin Kuang , Xiaolong Feng , Ting Li , Yongqi Zhang . Zwitterionic poly(ionic liquid)-induced fast structural diffusion electrolytes for lithium metal batteries. Chinese Chemical Letters, 2026, 37(9): 111344-. doi: 10.1016/j.cclet.2025.111344
17. [17]
  Bingke Zhang , Dongbo Wang , Jiamu Cao , Wen He , Gang Liu , Donghao Liu , Chenchen Zhao , Jingwen Pan , Sihang Liu , Weifeng Zhang , Xuan Fang , Liancheng Zhao , Jinzhong Wang . Tuning Stark effect by defect engineering on black titanium dioxide mesoporous spheres for enhanced hydrogen evolution. Chinese Chemical Letters, 2024, 35(11): 110254-. doi: 10.1016/j.cclet.2024.110254
18. [18]
  Xuyun Lu , Yanan Chang , Shasha Wang , Xiaoxuan Li , Jianchun Bao , Ying Liu . Hydrogen peroxide electrosynthesis via two-electron oxygen reduction: From pH effect to device engineering. Chinese Chemical Letters, 2025, 36(5): 110277-. doi: 10.1016/j.cclet.2024.110277
19. [19]
  Yuting Fu , Haoran Wang , Nan Li , Lujiao Mao , Xusheng Wang , Qipeng Li , Jinjie Qian . Pt inclusion effect on Ni-ABDC-derived PtNi-carbon nanomaterials for hydrogen evolution. Chinese Chemical Letters, 2025, 36(10): 110890-. doi: 10.1016/j.cclet.2025.110890
20. [20]
  Zhouze Chen , Yujie Yan , Jun Luo , Pengnian Shan , Changyu Lu , Feng Guo , Weilong Shi . Piezoelectric effect synergistically boosted NIR-driven photothermal-assisted photocatalytic hydrogen evolution. Chinese Chemical Letters, 2025, 36(10): 111302-. doi: 10.1016/j.cclet.2025.111302

Get Citation

PDF

XML

Metrics

PDF Downloads(7)
Abstract views(1085)
HTML views(88)

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