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Ionic-Liquid-Based Aqueous Two-Phase Systems Induced by Intra- and Intermolecular Hydrogen Bonds.

ABSTRACT: In recent years, aqueous two-phase systems (ATPSs) have been widely used in different fields and have become an increasingly attractive subject due to their application in the separation and purification of biomolecules. In this work, the aqueous phase behavior of ionic liquids (ILs) was modulated by changing the cis-trans structure of the anion in ILs. With the same tetra-butyl-phosphine as the cation, the cis-anion exhibited upper critical solution temperature (UCST) phenomena. In contrast, the trans-anion exhibited lower critical solution temperature (LCST) phenomena. The proposed mechanism shows that the main factors responsible for these phenomena include variations in the dissociation degree with temperature and the steric hindrance of the ILs. This phase behavior combines the chemical equilibrium in a solution with the microstructure of the molecule and is useful for constructing new chemical dynamic equilibria in ATPS. As an example of its application, aqueous solutions of both ILs can be used for the efficient separation and extraction of specific amino acids. The two ATPS systems reported in this work highlight a simple, effective, and environmentally friendly method for separating small biological molecules.

SUBMITTER: Xu W

PROVIDER: S-EPMC9414173 | biostudies-literature | 2022 Aug

REPOSITORIES: biostudies-literature

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Ionic-Liquid-Based Aqueous Two-Phase Systems Induced by Intra- and Intermolecular Hydrogen Bonds.

Xu Wenzhuo W Gao Xinpei X Zheng Liqiang L Lu Fei F

Molecules (Basel, Switzerland) 20220819 16

In recent years, aqueous two-phase systems (ATPSs) have been widely used in different fields and have become an increasingly attractive subject due to their application in the separation and purification of biomolecules. In this work, the aqueous phase behavior of ionic liquids (ILs) was modulated by changing the <i>cis</i>-<i>trans</i> structure of the anion in ILs. With the same tetra-butyl-phosphine as the cation, the cis-anion exhibited upper critical solution temperature (UCST) phenomena. I ...[more]

PMID: 36014543

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Project description:Intra- and intermolecular interactions have been explored in selected N-oxide derivatives: 2-(N,N-dimethylamino-N-oxymethyl)-4,6-dimethylphenyl (1) and 5,5'-dibromo-3-diethylaminomethyl-2,2'-biphenol N-oxide (2). Both compounds possess intramolecular hydrogen bonding, which is classified as moderate in 1 and strong in 2, and resonance-assisted in both cases. Density Functional Theory (DFT) in its classical formulation as well as Time-Dependent extension (TD-DFT) were employed to study proton transfer phenomena. The simulations were performed in the gas phase and with implicit and explicit solvation models. The obtained structures of the studied N-oxides were compared with experimental data available. The proton reaction path was investigated using scan with an optimization method, and water molecule reorientation in the monohydrate of 1 was found upon the proton scan progress. It was found that spontaneous proton transfer phenomenon cannot occur in the electronic ground state of the compound 1. An opposite situation was noticed for the compound 2. The changes of nucleophilicity and electrophilicity upon the bridged proton migration were analyzed on the basis of Fukui functions in the case of 1. The interaction energy decomposition of dimers and microsolvation models was investigated using Symmetry-Adapted Perturbation Theory (SAPT). The simulations were performed in both phases to introduce polar environment influence on the interaction energies. The SAPT study showed rather minor role of induction in the formation of homodimers. However, it is worth noticing that the same induction term is responsible for the preference of water molecules' interaction with N-oxide hydrogen bond acceptor atoms in the microsolvation study. The Natural Bond Orbital (NBO) analysis was performed for the complexes with water to investigate the charge flow upon the polar environment introduction. Finally, the TD-DFT was applied for isolated molecules as well as for microsolvation models showing that the presence of solvent affects excited states, especially when the N-oxide acceptor atom is microsolvated.

Dataset Information

Ionic-Liquid-Based Aqueous Two-Phase Systems Induced by Intra- and Intermolecular Hydrogen Bonds.

Publications

Ionic-Liquid-Based Aqueous Two-Phase Systems Induced by Intra- and Intermolecular Hydrogen Bonds.

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