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Interaction and Mechanism between Imidazolium Ionic Liquids and the Zwitterionic Amino Acid Tyr: a DFT Study
Wu, Zhiwei1,2; Ding, Weilu1; Zhang, Yaqin1; Wang, Yanlei1; He, Hongyan1,3
2021-10-15
Source PublicationACTA PHYSICO-CHIMICA SINICA
ISSN1000-6818
Volume37Issue:10Pages:10
AbstractIonic 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 pi(+)-pi stacking interactions between the imidazole and benzene rings are dominant during C2-methylation, while H-bonding and C-Alkyl-H center dot center dot center dot pi 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.
KeywordIonic liquids Zwitterionic amino acid Interaction and mechanism Hydrogen bond effect Van der Weals effect
DOI10.3866/PKU.WHXB202002021
Language英语
WOS KeywordPERTURBATION-THEORY APPROACH ; DENSITY-FUNCTIONAL THEORY ; NONCOVALENT INTERACTIONS ; ELECTRONIC-STRUCTURE ; HYDROGEN-BONDS ; DYNAMICS ; EXTRACTION ; STABILITY ; SOLVENTS
Funding ProjectNational Science Fund for Excellent Young Scholars, China[21922813] ; Key Program of National Natural Science Foundation of China[21834006] ; General program of National Natural Science Foundation of China[21978027] ; Key Research Program of Frontier Sciences of CAS[QYZDB-SSW-SLH022] ; Youth Innovation Promotion Association of CAS[2017066]
WOS Research AreaChemistry
WOS SubjectChemistry, Physical
Funding OrganizationNational Science Fund for Excellent Young Scholars, China ; Key Program of National Natural Science Foundation of China ; General program of National Natural Science Foundation of China ; Key Research Program of Frontier Sciences of CAS ; Youth Innovation Promotion Association of CAS
WOS IDWOS:000668419400009
PublisherPEKING UNIV PRESS
Citation statistics
Document Type期刊论文
Identifierhttp://ir.ipe.ac.cn/handle/122111/49307
Collection中国科学院过程工程研究所
Corresponding AuthorHe, Hongyan
Affiliation1.Chinese Acad Sci, Inst Proc Engn, Beijing Key Lab Ion Liquids Clean Proc, Beijing 100190, Peoples R China
2.Univ Chinese Acad Sci, Sino Danish Coll, Beijing 100049, Peoples R China
3.Zhengzhou Inst Emerging Ind Technol, Zhengzhou 450000, Peoples R China
Recommended Citation
GB/T 7714
Wu, Zhiwei,Ding, Weilu,Zhang, Yaqin,et al. Interaction and Mechanism between Imidazolium Ionic Liquids and the Zwitterionic Amino Acid Tyr: a DFT Study[J]. ACTA PHYSICO-CHIMICA SINICA,2021,37(10):10.
APA Wu, Zhiwei,Ding, Weilu,Zhang, Yaqin,Wang, Yanlei,&He, Hongyan.(2021).Interaction and Mechanism between Imidazolium Ionic Liquids and the Zwitterionic Amino Acid Tyr: a DFT Study.ACTA PHYSICO-CHIMICA SINICA,37(10),10.
MLA Wu, Zhiwei,et al."Interaction and Mechanism between Imidazolium Ionic Liquids and the Zwitterionic Amino Acid Tyr: a DFT Study".ACTA PHYSICO-CHIMICA SINICA 37.10(2021):10.
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