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Chiroptical Detectors for the Study of Unusual Phenomena in Chiral Chromatography

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Book cover Differentiation of Enantiomers I

Part of the book series: Topics in Current Chemistry ((TOPCURRCHEM,volume 340))

Abstract

Differentiation of enantiomers in chromatography requires specific detectors, based on polarimetry or circular dichroism. Their use is limited to chiral HPLC and SFC. We explain the operating principles of the different chiroptical detectors available and stress the influence of working wavelength and mobile phase on the output signal. Current and relevant applications of chiroptical detectors are absolute configuration assignment, measurement of enantiomeric excesses in complex mixtures and determination of elution order. We focus on the reversals of enantiomeric elution order, an important subject for the understanding of the chiral recognition mechanisms. We review the main parameters which can induce a reversal, show the usefulness of chiroptical detectors to easily identify reversals and emphasize the significance of the isoenantioselective temperature. The aim of this chapter is to highlight the valuable information provided by chiroptical detectors to study unusual behaviour in chiral HPLC and SFC, reversals of enantiomeric elution order and exchange phenomena as dynamic chromatography and self-disproportionation on achiral columns.

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Abbreviations

1-PrOH:

Propan-1-ol

2-PrOH:

Propan-2-ol

AcOH:

Acetic acid

CD:

Electronic circular dichroism

CIP:

Cahn–Ingold–Prelog priority rule

CSP:

Chiral stationary phase

DEA:

Diethylamine

ee:

Enantiomeric excess

FA:

Formic acid

HPLC:

High performance liquid chromatography

k:

Retention factor

L:

Liter(s)

LED:

Light-emitting diode

min:

Minute(s)

MPLC:

Medium pressure liquid chromatography

nd:

Not determined

nm:

Nanometer(s)

ORD:

Optical rotatory dispersion

RI:

Refractive index

SFC:

Supercritical or subcritical fluid chromatography

SMB:

Simulated moving bed

TFA:

Trifluoroacetic acid

THF:

Tetrahydrofuran

T iso :

Isoenantioselective temperature

UV:

Ultraviolet

α:

Enantioselectivity, ratio of retention factors for two enantiomers

β:

Phase ratio, ratio of the volume of the mobile phase and stationary phase in the column

μg:

Microgram

μL:

Microliter

Chiral-AGP:

α1-Acid glycoprotein

Chiralcel OB:

Cellulose tris benzoate (Daicel)

Chiralcel OD:

Cellulose tris(3,5-dimethylphenyl-carbamate) coated (Daicel)

Chiralcel OJ:

Cellulose tris(4-methylbenzoate) (Daicel)

Chiralpak AD:

Amylose tris(3,5-dimethylphenyl-carbamate) coated (Daicel)

Chiralpak AS:

Amylose tris([(S)alpha-phenethyl]-carbamate) coated (Daicel)

Chiralpak IA:

Amylose tris(3,5-dimethylphenyl-carbamate) immobilised (Daicel)

Chiralpak IB:

Cellulose tris(3,5-dimethylphenyl-carbamate) immobilised (Daicel)

Chiralpak IC:

Cellulose tris(3,5-dichlorophenyl-carbamate) immobilised (Daicel)

Chiralpak ID:

Amylose tris(3-chlorophenyl-carbamate) immobilised (Daicel)

Lux-Cellulose-1:

Cellulose tris(3,5-dimethylphenyl-carbamate) coated (Phenomenex)

Lux-Cellulose-2:

Cellulose tris(3-chloro-4-methylphenyl-carbamate) coated (Phenomenex)

Lux-Cellulose-4:

Cellulose tris(4-chloro-3-methylphenyl-carbamate) coated (Phenomenex)

Regispack:

Amylose tris(3,5-dimethylphenyl-carbamate) coated (Regis Technologies)

Ultron ES-OVM:

Ovomucoid protein bonded

(S,S)-Whelk-O1:

(3R,4S)-4-(3,5-Dinitrobenzamido)-3-[3-(dimethylsilyloxy)propyl]-1,2,3,4-tetrahydrophenanthrene (Regis Technologies)

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    Nicolas Vanthuyne & Christian Roussel

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    Volker Schurig

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Vanthuyne, N., Roussel, C. (2013). Chiroptical Detectors for the Study of Unusual Phenomena in Chiral Chromatography. In: Schurig, V. (eds) Differentiation of Enantiomers I. Topics in Current Chemistry, vol 340. Springer, Cham. https://doi.org/10.1007/128_2013_441

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