Effect of 2-propanol content on solute retention mechanisms determined using amylose tris(3,5-dimethylphenylcarbamate) chiral stationary phase under normal- and reversed-phase conditions

Tsui, Hung‐Wei; Zhang, Honglin; Hsieh, Ching‐Hung

doi:10.1016/j.chroma.2021.462226

Cited by 7 publications

(19 citation statements)

References 36 publications

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“…1365 A similar approach was reported for the enantioseparation of 1indanol using inverse method in order to derive adsorption isotherms 1366 as well as to study the effect of the column dimension. 1367,1368 Recently, a series of interesting studies on the application of adsorption methods for mechanistic studies on enantioselective selector−selectand interactions in chromatography were published by Asnin's, 1369 Tsui's, 1370,1371 Felinger's, 1224 Cavazzini's, 1372,1373 and a few other groups. 1374 Just a very few of these studies are briefly summarized below, whereas earlier studies on this topic were summarized by Asnin.…”

Section: Nuclear Magnetic Resonancementioning

confidence: 99%

“…1371 An immobilized ADMPC-based sorbent was also used by the same research group with the aim of investigating the effect of electrostatic and solvophobic interactions, with complementary effects on solute retention with changing propan-2-ol concentration. 1370 The idea was to use the curvature of the logarithm of the retention factor versus the logarithm of the propan-2-ol concentration for obtaining information on the retention mechanisms in both NP and RP modes. In addition, the slope values of the curves were related to the number of displaced propan-2-ol molecules upon solute adsorption.…”

Section: Nuclear Magnetic Resonancementioning

confidence: 99%

“…At propan-2-ol concentrations beyond 40 vol %, the presence of pantolactone−sorbent electrostatic interactions enhanced the enantioselective recognition. 1370 In several studies, it has been observed that polysaccharidebased CSPs, under aqueous-organic MP conditions, do not follow a typical RP mechanism, but rather an HILIC separation mechanism. 51,677,1222,1223,1225,1226 The generally accepted understanding is that HILIC-type separations are associated with some partition mechanism of analytes between the MP and a layer of water-enriched MP present at the surface of the CSP.…”

Section: Nuclear Magnetic Resonancementioning

confidence: 99%

“…Recently, a series of interesting studies on the application of adsorption methods for mechanistic studies on enantioselective selector–selectand interactions in chromatography were published by Asnin’s, Tsui’s, , Felinger’s, Cavazzini’s, , and a few other groups . Just a very few of these studies are briefly summarized below, whereas earlier studies on this topic were summarized by Asnin .…”

Section: Trends In Enantioselective Recognition In Separation Science...mentioning

confidence: 99%

“…Tsui and co-workers studied the effect of acetone, propan-2-ol, and tert -butanol as polar MP modifiers on the enantioselectivities of four structurally related chiral compounds on the column based on cellulose tris (3,5-dimethylphenylcarabamate) immobilized onto silica . The enantioselectivities, α, of benzoin and methyl mandelate decreased with an increasing polar modifier content in the MP, whereas the selectivity of separation of pantolactone enantiomers increased with increasing acetone content in the MP.…”

Section: Trends In Enantioselective Recognition In Separation Science...mentioning

confidence: 99%

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Recognition in the Domain of Molecular Chirality: From Noncovalent Interactions to Separation of Enantiomers

2022

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It is not a coincidence that both chirality and noncovalent interactions are ubiquitous in nature and synthetic molecular systems. Noncovalent interactivity between chiral molecules underlies enantioselective recognition as a fundamental phenomenon regulating life and human activities. Thus, noncovalent interactions represent the narrative thread of a fascinating story which goes across several disciplines of medical, chemical, physical, biological, and other natural sciences. This review has been conceived with the awareness that a modern attitude toward molecular chirality and its consequences needs to be founded on multidisciplinary approaches to disclose the molecular basis of essential enantioselective phenomena in the domain of chemical, physical, and life sciences. With the primary aim of discussing this topic in an integrated way, a comprehensive pool of rational and systematic multidisciplinary information is provided, which concerns the fundamentals of chirality, a description of noncovalent interactions, and their implications in enantioselective processes occurring in different contexts. A specific focus is devoted to enantioselection in chromatography and electromigration techniques because of their unique feature as “multistep” processes. A second motivation for writing this review is to make a clear statement about the state of the art, the tools we have at our disposal, and what is still missing to fully understand the mechanisms underlying enantioselective recognition.

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Section: Nuclear Magnetic Resonancementioning

confidence: 99%

Section: Nuclear Magnetic Resonancementioning

confidence: 99%

Section: Nuclear Magnetic Resonancementioning

confidence: 99%

Section: Trends In Enantioselective Recognition In Separation Science...mentioning

confidence: 99%

Section: Trends In Enantioselective Recognition In Separation Science...mentioning

confidence: 99%

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Recognition in the Domain of Molecular Chirality: From Noncovalent Interactions to Separation of Enantiomers

2022

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Effect of mobile‐phase modifiers on the enantioselective retention behavior of methyl mandelate with an amylose 3,5‐dimethylphenylcarbamate chiral stationary phase under reversed‐phase conditions

Tsui

Hsieh

Zhan

2022

J of Separation Science

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In this study, methanol, ethanol, n‐propyl alcohol, isopropyl alcohol, acetone, and tert‐butanol were used as organic modifiers in reversed‐phase mode chiral liquid‐chromatography to systematically investigate the effects of mobile phase components on the enantioselective retention behavior of methyl mandelate with immobilized amylose 3,5‐dimethylphenylcarbamate‐based sorbent called Chiralpak IA. A two‐site enantioselective model was used to obtain information on the recognition mechanisms by observing the dependence of the enantioselectivity and retention factor difference on the modifier content. Similar enantioselective retention behaviors were observed for all modifiers, and characteristic modifier concentration points (PL, PM, and PH) were identified. At modifier concentrations up to PM, the weakened hydrophobic environment resulted in polymer structural relaxation, which changed the recognition mechanisms. By contrast, at concentrations beyond PH, considerably different enantioselectivity behaviors were observed, indicating that the existence of dipole‐dipole interaction, which was stronger at higher modifier concentrations, contributed to the retention mechanisms. The concentrations at which these characteristic points occurred were dependent on the carbon number of the modifier molecule. Modifiers with more carbon numbers facilitated the transition in the enantioselective behaviors. These results demonstrated that the proposed method can provide a physically consistent quantitative description of enantioselective retention behavior in reversed‐phase mode.

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Fundamentals of enantioselective liquid chromatography

Peluso

Chankvetadze

2023

Liquid Chromatography

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Effect of 2-propanol content on solute retention mechanisms determined using amylose tris(3,5-dimethylphenylcarbamate) chiral stationary phase under normal- and reversed-phase conditions

Cited by 7 publications

References 36 publications

Recognition in the Domain of Molecular Chirality: From Noncovalent Interactions to Separation of Enantiomers

Recognition in the Domain of Molecular Chirality: From Noncovalent Interactions to Separation of Enantiomers

Effect of mobile‐phase modifiers on the enantioselective retention behavior of methyl mandelate with an amylose 3,5‐dimethylphenylcarbamate chiral stationary phase under reversed‐phase conditions

Fundamentals of enantioselective liquid chromatography

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