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
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