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
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