Ethyl Substituents Research Articles

Controlling the position of the nucleophilic ring-opening of 2-EWG-substituted azetidinium salts with fluoride by the N-1-(1-naphthyl)ethyl substituent and BINAM-derived bis-urea organocatalyst

BINAM (1,1′-binaphthyl-2,2′-diamine)-derived bis-urea-catalyzed nucleophilic ring-opening of optically active and diastereomerically pure 2-EWG (electron-withdrawing group)-substituted N-(1-(1-naphthyl)ethyl)azetidinium salts with cesium fluoride in dichloromethane at room temperature proceeds at the less sterically hindered 4-position over the electronically deficient 2-position. Selective ring-opening at the 4-position is achieved by the combination of chiral stereocenters, as in N-(1-(1-naphthyl)ethyl)azetidinium salt, and steric bulk of the chiral bis-urea catalysts. The reaction affords the corresponding γ-fluoro-α-aminobutyric acid derivatives in diastereomerically pure. This protocol is applicable to the synthesis of enantiomerically enriched (98 % ee) γ-fluoro-α-amino acid derivatives starting from the commercially available chiral 1-(1-naphthyl)ethylamine.

Exploring the Potential of Isoindole‐1,3‐Dione Derivatives as Novel Inhibitors of Aldose Reductase: An In Silico and In Vitro Insight into Therapeutic Strategies for Diabetic Complications

AbstractThis study explores the potential of isoindole‐1,3‐dione derivatives as novel inhibitors of aldose reductase (AR), focusing on their in silico and in vitro effects for therapeutic strategies against diabetic complications. Aldose reductase, a critical enzyme in the polyol pathway, plays a significant role in glucose metabolism and has been linked to diabetic complications. In this comprehensive study, isoindole‐1,3‐dione derivatives were synthesized and evaluated for their inhibitory effects on the recombinant human AR enzyme. The compounds’ inhibitory activities were measured both in vitro and through in silico techniques, employing molecular docking and free binding energy calculations and ADME studies. The newly synthesized compounds demonstrated varied inhibitory effects, with ethyl and phenyl substituents at specific positions enhancing inhibitory activity. Notably, compounds with carboxylic acid derivatives exhibited potent inhibitory effects, especially compound 6 with an IC50 value of 1.649 μM. In conclusion, this study provides valuable insights into the inhibitory potential of isoindole‐1,3‐dione derivatives against AR, suggesting their potential therapeutic application in mitigating diabetic complications. The combination of experimental and computational approaches offers a comprehensive understanding of the compounds’ interaction mechanisms and pharmacokinetic profiles, supporting their further exploration as antidiabetic agents.

Soft confinement of water in aliphatic alcohols: MIR/NIR spectroscopic and DFT studies

Here, we present the first examination of the state of water under a soft confinement in eight aliphatic alcohols including cyclopentanol, 1-pentanol, 1-hexanol, 1-heptanol, 1-octanol, 1-decanol, 2-octanol and 3-octanol. Due to relatively large size of the aliphatic part, water has limited solubility in all studied alcohols. Water content in saturated solutions was determined by Karl Fischer titration and correlated with the spectroscopic data. This way, we determined the molar absorptivity of the ν2+ν3 combination mode. The effect of addition of water and temperature variation was monitored by ATR-IR and NIR spectroscopy. Analysis of the experimental results was guided by DFT calculations, which provided the structures, harmonic MIR spectra and binding energies of selected alcohol-water complexes.Our studies demonstrated that the state of water in alcohols is related to its solubility, which depends on structure of solvent molecules. The solubility of water in 1-alcohols decreases on increasing of the chain length, but for long chain alcohols this effect is less evident. More apparent solubility reduction appears in going from the primary to secondary alcohols. The effective shielding of the OH group in the linear alcohols is achieved when on both sides of the OH group are ethyl or longer substituents, while the shielding by methyl groups is less efficient. Water is much better soluble in the cyclic alcohols as compared with the linear ones due to better accessibility of the OH group.The soft confinement of water in aliphatic alcohols allows for flexible structural arrangements and interactions. Even at low water content, we did not observe free molecules of water. At these conditions, the molecules of water are singly or doubly bonded to the OH groups from the alcohol. Increasing solubility of water reduces the number of the free OH groups and leads to formation of water clusters. Obtained results allow concluding that in alcohols with sizable aliphatic part the molecules of water are confined in the vicinity of the OH groups.

Isomer‐Dependent Melting Behavior of Low Molar Mass Azobenzene Derivatives: Observation of a Higher Melting Z‐Isomer

AbstractAzobenzene compounds are putative solar thermal fuels (STF) due to the excellent photostability and structural control of isomerization rates. Azobenzenes, in which both Z‐ and E‐isomers are liquid at room temperature, are promising candidates for STF flow technology. A literature survey of melting points led to the synthesis and isomer separation of ortho‐ and meta‐monosubstituted azobenzenes with fluoro, methyl, ethyl, trifluoromethyl and methoxy substituents and several dimethyl substituted azobenzenes. Four of the compounds are liquid azobenzenes with higher specific energy than literature work with higher molar mass, liquid compounds. Eight of the compounds unexpectedly displayed a higher melting point for the Z‐isomer which is rarely observed. Intermolecular close contacts in the crystal lattice of the Z‐isomer are the main factor responsible for the higher melting temperatures.

Quantum Chemical-Based Investigations and Lipophilicity Evaluations on Some Structurally Related Quinazoline Derivatives

This work was chiefly conceived to explore the substituent effects on thermodynamic, electronic and lipophilic characteristics of some quinazoline derivatives (Q1-Q4) from theoretical aspects. The variations caused by methyl, ethyl, chlorine and bromine substituents on the same carbon of the aromatic ring were evaluated with a computational approach. In accordance with this purpose, simultaneously, DFT-based calculations were performed for vacuum and two different surroundings (DMSO and water) on methaqualone (Q1), etaqualone (Q2), mecloqualone (Q3), and mebroqualone (Q4) compounds by using the B3LYP functional and 6-311++G(d, p) split-valence triple zeta basis set. The computed thermodynamic quantities revealed that the halogen substitution was more preferable. The effect of substituent modification on electrostatic surface features was evaluated visually by molecular electrostatic potential (MEP) mapping technique. To shed light on the chemical reactivity behaviors of the Q1-Q4, DFT-based reactivity identifiers were computed. Also, the intramolecular interactions affected by substitution were evaluated on the basis of the Natural Bond Orbital (NBO) theory. The NBO results revealed that π-π* interactions predominate for each compound. The lipophilic character analyzes of the mentioned compounds were evaluated both numerically and visually. The data of both methods support each other.

Neutral Block Copolymer Assisted Gene Delivery using Hydrodynamic Limb Vein Injection.

Three different amphiphilic block copolymer families are synthesized to investigate new opportunities to enhance gene delivery via Hydrodynamic Limb Vein (HLV) injections. First a polyoxazoline-based family containing mostly one poly(2-methyl-2-oxazoline) (PMeOx) block and a second block POx with an ethyl (EtOx), isopropyl (iPrOx) or phenyl substituent (PhOx) is synthesized. Then an ABC poly(2-ethyl-2-oxazoline)-b-poly(2-n-propyl-2-oxazoline)-b-poly(2-methyl-2-oxazoline) triblock copolymer is synthesized, with a thermosensitive middle block. Finally, polyglycidol-b-polybutylenoxide-b-polyglycidol copolymers with various molar masses and amphiphilic balance are produced. The simple architecture of neutral amphiphilic triblock copolymer is not sufficient to obtain enhanced in vivo gene transfection. Double or triple amphiphilic neutral block copolymers are improving the in vivo transfection performances through HLV administration as far as a block having an lower critical solution temperature is incorporated in the vector. The molar mass of the copolymer does not seem to affect the vector performances in a significant manner.

Manipulation of the Self‐Assembly Morphology by Side‐Chain Engineering of Quinoxaline‐Substituted Organic Photothermal Molecules for Highly Efficient Solar‐Thermal Conversion and Applications

AbstractOrganic photothermal materials have attracted increasing attention because of their structural diversity, flexibility, and compatibility. However, their energy conversion efficiency is limited owing to the narrow absorption spectrum, strong reflection/transmittance, and insufficient nonradiative decay. In this study, two quinoxaline‐based D–A‐D–A‐D‐type molecules with ethyl (BQE) or carboxylate (BQC) substituents were synthesized. Strong intramolecular charge transfer provided both molecules with a broad absorption range of 350–1000 nm. In addition, the high reorganization energy and weak molecular packing of BQE resulted in efficient nonradiative decay. More importantly, the self‐assembly of BQE leads to a textured surface and enhances the light‐trapping efficiency with significantly reduced light reflection/transmittance. Consequently, BQE achieved an impressive solar‐thermal conversion efficiency of 18.16 % under 1.0 kW m−2 irradiation with good photobleaching resistance. Based on this knowledge, the water evaporation rate of 1.2 kg m−2 h−1 was attained for the BQE‐based interfacial evaporation device with an efficiency of 83 % under 1.0 kW m−2 simulated sunlight. Finally, the synergetic integration of solar‐steam and thermoelectric co‐generation devices based on BQE was realized without significantly sacrificing solar‐steam efficiency. This underscores the practical applications of BQE‐based technology in effectively harnessing photothermal energy. This study provides new insights into the molecular design for enhancing light‐trapping management by molecular self‐assembly, paving the way for photothermal‐driven applications of organic photothermal materials.

Manipulation of the Self-Assembly Morphology by Side-Chain Engineering of Quinoxaline-Substituted Organic Photothermal Molecules for Highly Efficient Solar-Thermal Conversion and Applications.

Organic photothermal materials have attracted increasing attention because of their structural diversity, flexibility, and compatibility. However, their energy conversion efficiency is limited owing to the narrow absorption spectrum, strong reflection/transmittance, and insufficient nonradiative decay. In this study, two quinoxaline-based D-A-D-A-D-type molecules with ethyl (BQE) or carboxylate (BQC) substituents were synthesized. Strong intramolecular charge transfer provided both molecules with a broad absorption range of 350-1000 nm. In addition, the high reorganization energy and weak molecular packing of BQE resulted in efficient nonradiative decay. More importantly, the self-assembly of BQE leads to a textured surface and enhances the light-trapping efficiency with significantly reduced light reflection/transmittance. Consequently, BQE achieved an impressive solar-thermal conversion efficiency of 18.16 % under 1.0 kW m-2 irradiation with good photobleaching resistance. Based on this knowledge, the water evaporation rate of 1.2 kg m-2 h-1 was attained for the BQE-based interfacial evaporation device with an efficiency of 83 % under 1.0 kW m-2 simulated sunlight. Finally, the synergetic integration of solar-steam and thermoelectric co-generation devices based on BQE was realized without significantly sacrificing solar-steam efficiency. This underscores the practical applications of BQE-based technology in effectively harnessing photothermal energy. This study provides new insights into the molecular design for enhancing light-trapping management by molecular self-assembly, paving the way for photothermal-driven applications of organic photothermal materials.

Cobalt(III) complexes with (±)-1,3-pentanediamine-N,N,N’,N’-tetraacetate. The influence of nature of alkali and alkaline earth metal counter cations on the supramolecular association of the complex

The coordination of hexadentate (±)-1,3-pentanediamine-N,N,N’,N’-tetraacetate (1,3-pndta) ligand with Co(III) has been investigated. Four octahedral [Co(1,3-pndta)]− complexes containing different counter cations, Li[Co(1,3-pndta)]⋅4H2O (1a), Li[Co(1,3-pndta)]⋅2H2O (1b), K[Co(1,3-pndta)]⋅H2O (1c) and Ca[Co(1,3-pndta)]2⋅5H2O (1d), were synthesized and structurally characterized. Single-crystal X-ray diffraction analysis, IR, NMR (1H and 13C) and electronic absorption spectroscopy were used for characterization of 1a − d. The influence of the ethyl substituent of 1,3-propanediamine chain in 1,3-pndta and the nature of metal counter cation on the structural modalities of carboxylate bridging groups in 1a − d were established by comparing with the analogous [M(1,3-pdta)] n − (1,3-pdta = 1,3-propanediamine-N,N,N’,N’-tetraacetate) and [M(1,3-pndta)] n − complexes (M = Co(III), Cr(III) and Ni(II)). Our studies have shown that the supramolecular association of the complexes is primarily governed by the size of the alkali or alkaline earth metal counter cation and its templating ability, while ethyl substituents, in most cases, prevent the formation of 3D polymeric frameworks.

Benzimidazolium bromide derivative inclusion complexes with native and modified beta-cyclodextrins

The interactions between four native and modified beta-cyclodextrins and a benzimidazolium bromide salt were analyzed through UV-Vis and NMR Spectroscopy. The new benzimidazolium salt was obtained by simple and efficient conversion of N-1 substituted 5,6-dimethylbenzimidazole with phenacyl bromide in acetone. In all cases, the complexes stoichiometry was 1:1, as determined from UV-Vis titrations. Based on the values for association constants, the strength of the interactions with benzimidazolium bromide was weakest with the methyl substituted beta-cyclodextrin and strongest with the sulfobutylether substituted beta-cyclodextrin. Through-space NOE experiments were used to investigate the structural aspects of inclusion process. The obtained NOE correlations indicate coexistence of two inclusion modes: one with the phenacyl group inside the cyclodextrin cavity and the second one with dimethyl-substituted benzene ring inside the cavity. The imidazole ring and the ethyl substituent have been proven to remain outside the cyclodextrin cavity in both inclusion modes.

Introducing Propionate and 2-Dimethylammonium Chloride Ethyl Substituents onto Cornstarch for Acquiring Good Film Properties and Easy Desizing from Sized Warps

Introducing Propionate and 2-Dimethylammonium Chloride Ethyl Substituents onto Cornstarch for Acquiring Good Film Properties and Easy Desizing from Sized Warps

Solvent and alkyl substitution effects on charge-transfer mediated triplet state generation in BODIPY dyads: a combined computational and experimental study

Donor–acceptor dyads based on BODIPYs have been recently employed to enhance the formation of triplet excited states with the process of spin–orbit charge transfer intersystem crossing (SOCT-ISC) which does not require introduction of transition metals or other heavy atoms into the molecule. In this work we compare two donor–acceptor dyads based on meso-naphthalenyl BODIPY by combining experimental and computational investigations. The photophysical and electrochemical characterization reveals a significant effect of alkylation of the BODIPY core, disfavoring the SOCT-ISC mechanism for the ethylated BODIPY dyad. This is complemented with a computational investigation carried out to rationalize the influence of ethyl substituents and solvent effects on the electronic structure and efficiency of triplet state population via charge recombination (CR) from the photoinduced electron transfer (PeT) generated charge-transfer (CT) state. Time dependent-density functional theory (TD-DFT) calculations including solvent effects and spin–orbit coupling (SOC) calculations uncover the combined role played by solvent and alkyl substitution on the lateral positions of BODIPY.Graphical abstract

Origin of Long-Range Hyperfine Couplings in the EPR Spectra of 2,2,5,5-Tetraethylpyrrolidine-1-oxyls.

Cyclic nitroxides with several bulky alkyl substituents adjacent to the nitroxide group are known to demonstrate a much higher stability to bioreduction than their tetramethyl analogues. Among these so-called "sterically shielded" nitroxides, the pyrrolidine derivatives are the most stable. The EPR spectra of some sterically shielded pyrrolidine-1-oxyls were reported to show one or two large additional doublet splittings with a hyperfine coupling (hfc) constant (ca. 0.2-0.4 mT). To determine the origin of these hfc, a series of 2-R-2,5,5-triethyl-3,4-bis(hydroxymethyl)-pyrrolidine-1-oxyls with methylene groups stereospecifically enriched with deuterium were prepared, and their CW EPR spectra were studied. In addition, these nitroxides were investigated using quantum chemical calculations on the UB3LYP/def2-TZVP level and NBO analysis. The apparent constants were assigned to hfc with γ-hydrogen in the side chain, with the contribution of the NBO orbital βπ*(N-O) to the natural localized molecular orbital βσ(C-H) playing the major role. This interaction is efficient if the ethyl substituent is in the pseudoaxial position of the ring and the CH2-CH3 bond is codirected with (parallel to) N-O. The apparent constant aH increases with the Boltzmann population of this conformation.

Novel Sulfone 2-Aminobenzimidazole Derivatives and Their Coordination Compounds: Contribution of the Ethyl and Phenyl Substituents on Non-Covalent Molecular Interactions; Biological Antiproliferative Activity

New sulfone 2-aminobenzimidazole derivatives were designed and synthesized. Their nickel(II), copper(II), zinc(II), cadmium(II) and mercury(II) compounds were obtained and fully characterized by spectroscopic and analytical techniques. Single crystal X-ray structural analysis was performed in order to study the relevant intra and inter non-covalent interactions, mainly H···π, lone pair···π, and π···π, highlighting the difference between the terminal ethyl and phenyl groups in such interactions. Dimeric and trimeric supramolecular syntons were found for some of these compounds. Additionally, their antiproliferative activity was investigated, finding that the copper(II) compounds with the sulfone phenyl derivative were the most active.

Vinyl Phosphonates as Photopharmacological Agents: Laser‐Induced Cis‐Trans Isomerization and Butyrylcholinesterase Activity

AbstractPhotoswitchable molecules are highly requested compounds in various fields and, in particular, biomedicine. The urgent modern task of photopharmacology (an emerging approach in medicine) is the design of molecules that have both photoswitchable and bioactive properties. In this study, we present vinyl phosphonates – diene compounds with ethyl and isopropyl substituents on the phosphonate group. Both compounds demonstrated laser‐induced cis‐trans isomerization via a C=C bond after irradiation at 266 nm. The photoisomerization quantum yield was 17 % and 20 % for compounds with ethyl and isopropyl groups, respectively. The main advantage of the presented vinyl phosphonates is their bioactivity, unlike other photoswitchable molecules. Rather efficient butyrylcholinesterase inhibition by both presented compounds was demonstrated by IPC‐Micro analysis. The notable butyrylcholinesterase inhibition increase by 5 and 9 times was found for the vinyl phosphonates after laser irradiation. Such a sizeable difference in inhibition values for different isomeric states is a critical factor, which opens the way toward promising applications of vinyl phosphonates as photopharmacological agents.

Protolytic and Complexing Properties of Isomeric N-(Pyridylethyl)taurines

New N-derivatives of taurine, N-[2-(2-pyridyl)ethyl]taurine (HL1) and N-[2-(4-pyridyl)ethyl]taurine (HL2) have been synthesized. Using the method of alkalimetric titration of aqueous solutions with pH potentiometric indication at I = 0.1 mol/L (KCl/KNO3) and T = 25 ± 1°C, the acid dissociation constants of functional groups in the composition of reagents have been determined (HL1: pKa0 = 3.80 ± 0.03, pKa1 = 8.67 ± 0.02, HL2: pKa0 = 4.80 ± 0.05, pKa1 = 8.18 ± 0.04). It has been found that reagent HL1 is more resistant to the degradation process. The complexation of transition and alkaline earth metal ions with НL1 has been studied. It has been shown that the introduction of a 2-(2-pyridyl)ethyl substituent into the structure of taurine leads to a significant increase in the stability (Δ log β ≥ 1) of copper(II), cobalt(II), nickel(II), zinc(II), cadmium(II) and silver(I) complexes with НL1. Calcium(II), magnesium(II), strontium(II), and barium(II) complexes with HL1 are characterized by a slight increase in stability (Δ lg β 1) compared to taurine. Based on the data obtained, the structure of the studied complexes have been assumed.

Aqueous Polyelectrolyte Electrodeposition: The Effects of Alkyl Substitution and Varying Supporting Electrolyte Concentrations on the Deposition Efficiency

AbstractThe controlled growth of surface‐modifying polymer films by electrodeposition often fails because of the lack of redox activity of these compounds. Here, electroactive complexants help to electrodeposit non‐electroactive polymers. Hence, we investigate the counterion‐induced electrodeposition of polyelectrolytes: three quaternized poly(N,N‐dialkylaminoethyl methacrylate)s (qPDAAEMA), in particular their methyl, ethyl, and isopropyl derivatives (i. e. qPDMAEMA, qPDEAEMA, and qPDPAEMA), provide transparent solutions in the presence of hexacyanoferrate(II) (ferrocyanide) at specific concentration windows of the KCl supporting electrolyte. Below a certain KCl concentration, insolubility dominates irrespective of the hexacyanoferrate valency, whilst above an upper threshold, full solubility is observed. Between these limits, oxidation reversibly electrodeposits polymer/hexacyanoferrate(III) (ferricyanide) complexes. Hydrodynamic voltammetry (and data analysis using in‐house software) provides access to the deposition efficiency (DE). qPDEAEMA with ethyl substituents shows highest DEs; larger or smaller substituents fall short because of a balance between “hydrophobicity” and charge separation, shifting the window toward smaller salt concentrations with increasing alkyl size. We always observe a DE maximum close to the minimum salt concentration, whilst electrochemical quartz crystal microbalance (EQCM) measurements indicate a change in film water content close to the maximum. These effects, being also discussed in terms of polymer conformation, can direct the future engineering of electroassisted coatings.

Aqueous biphasic systems comprising analogues of glycine-betaine ionic liquids: Toward greener separation platforms

The use of biobased and bioactive compounds has boosted the development of sustainable extraction and purification processes, in which ionic liquids have been playing a major role. Ionic-liquid-based aqueous biphasic systems (IL-based ABS) have been raising significant interest as advantageous extraction and purification platforms; however, imidazolium-based ILs have been the primary option as phase-forming agents. Aiming the development of more sustainable IL-based ABS, in this work, six novel analogues of glycine-betaine ILs (AGB-ILs) were investigated. These ILs were synthesized and characterized in terms of purity, physico-chemical properties, ecotoxicity and ability to form ABS with tri-potassium citrate. The investigated AGB-ILs are composed of tri(n-alkyl[2-ethoxy-2-oxoethyl]ammonium/phosphonium and tri(n-alkyl[4-ethoxy-4-oxobutyl]ammonium/phosphonium cations with ethyl, n-propyl and n-butyl substituents, and the tosylate ([Tos]-) anion. The synthesized ILs present degradation temperatures in the range from 220 to 265 °C, and are classified as relatively harmless regarding their ecotoxicity. The studied AGB-ILs display slightly lower thermal stability, but yet a lower ecotoxicity compared to the commercial IL 1-butyl-3-methylimidazolium tosylate. Their ability to form ABS was assessed, allowing to conclude that an expansion in the alkyl side chain length and spacer, as well as the presence of phosphonium instead of ammonium as central atom, increase the ability for phase separation in presence of tri-potassium phosphate aqueous solutions. The extraction performance of the studied AGB-ILs-based ABS was finally assessed with furfural, a platform chemical. In the majority of the studied systems, furfural preferentially migrates to the AGB-IL-rich phase, obtaining extraction efficiencies in a single step to the IL-rich phase up to 98%. These results reveal that novel ABS comprising AGB-ILs can be potentially used as separation platforms of bioactive compounds.

Approaching enzymatic catalysis with zeolites or how to select one reaction mechanism competing with others

Approaching the level of molecular recognition of enzymes with solid catalysts is a challenging goal, achieved in this work for the competing transalkylation and disproportionation of diethylbenzene catalyzed by acid zeolites. The key diaryl intermediates for the two competing reactions only differ in the number of ethyl substituents in the aromatic rings, and therefore finding a selective zeolite able to recognize this subtle difference requires an accurate balance of the stabilization of reaction intermediates and transition states inside the zeolite microporous voids. In this work we present a computational methodology that, by combining a fast high-throughput screeening of all zeolite structures able to stabilize the key intermediates with a more computationally demanding mechanistic study only on the most promising candidates, guides the selection of the zeolite structures to be synthesized. The methodology presented is validated experimentally and allows to go beyond the conventional criteria of zeolite shape-selectivity.

The way for improving the efficiency of ammonia and carbon dioxide absorption of choline chloride: Urea mixtures by modifying a choline cation

In the current work, two novel systems formed by chlorides of choline family (ChCl), namely ammonium salts with 2-hydroxyethyl and 2-(2-hydroxyethoxy)ethyl substituents, and urea (U) in a molar ratio 1 : 1 were obtained. Their densities (ρ), viscosities (η), refractive indices (nD) and properties related to the carbon dioxide and ammonia absorption were carefully investigated in a wide temperature range. The solubilities of NH3 and CO2 in the prepared mixtures at T = (303.2–333.2) K and p = (100–639) kPa were measured and linear correlation were used for fitting the experimental data. Based on this, the Henry's law constants both in a molality (Hm) and in a molar fraction scales (Hx), and the changes of enthalpy (ΔsolH∘), Gibbs free energy (ΔsolG∘) and entropy (ΔsolS∘) during the absorption process were calculated. The absorption capacity at 313.2 K and 101 kPa of the mixtures comprising new OH-grafted hydrogen bond acceptors (HBA) were found to be higher by 60 % for NH3 and 17% for CO2 when one methyl in choline cation is exchanged by a 2-hydroxyethyl group, by 103% for NH3 and 27% for CO2 when two methyls are exchanged by two 2-hydroxyethyl groups, by 9% for NH3 and 51% for CO2 when one methyl is exchanged by a 2-(2-hydroxyethoxy)ethyl group, and by 30% for NH3 and 73% for CO2 when two methyls are exchanged by one 2-hydroxyethyl and one 2-(2-hydroxyethoxy)ethyl groups compared to the referent deep eutectic solvent (ChCl : 1.5U). This assumes occurring the ammonia capture via most likely H-bonding interactions between the NH3 molecule(s) and the hydroxyalkyl fragments, while the ether's groups in HBA structure depress the positive effect of latter and hence decrease the general ammonia's solubility in the considered mixtures. In case of carbon dioxide, the absorption capacity of the studied mixtures correlates well with the free volume of the fluid.