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Valine derived poly (acetylenes) as versatile chiral lyotropic liquid crystalline alignment media for RDC‐based structure elucidations

Krupp, Alexis ; Noll, Markus ; Reggelin, Michael (2021)
Valine derived poly (acetylenes) as versatile chiral lyotropic liquid crystalline alignment media for RDC‐based structure elucidations.
In: Magnetic Resonance in Chemistry, 59 (5)
doi: 10.1002/mrc.5003
Artikel, Bibliographie

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Kurzbeschreibung (Abstract)

Anisotropic samples of lyotropic liquid crystalline (LLC) phases of valine derived polyaryl acetylenes were employed as chiral alignment media for the measurement of residual dipolar couplings (RDCs) of 12 small, chiral, organic molecules. The quadrupolar splitting of the deuterium signal of CDCl₃ can be adjusted by temperature and concentration changes from 0 to 350 Hz. The LLC phases showed excellent orienting properties for all analytes bearing various functional groups. The precise extraction of RDCs in the range of up to ±30 Hz from F2‐coupled HSQC spectra was possible. Additionally, the chiral environment led to diastereomorphous interactions with the enantiomers of chiral analytes leading to two different sets of RDCs. This differential order effect was particularly pronounced with H‐bond donors like alcohols and 2° amines.

Typ des Eintrags: Artikel
Erschienen: 2021
Autor(en): Krupp, Alexis ; Noll, Markus ; Reggelin, Michael
Art des Eintrags: Bibliographie
Titel: Valine derived poly (acetylenes) as versatile chiral lyotropic liquid crystalline alignment media for RDC‐based structure elucidations
Sprache: Englisch
Publikationsjahr: 2021
Ort: Chichester
Verlag: John Wiley & Sons
Titel der Zeitschrift, Zeitung oder Schriftenreihe: Magnetic Resonance in Chemistry
Jahrgang/Volume einer Zeitschrift: 59
(Heft-)Nummer: 5
DOI: 10.1002/mrc.5003
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Kurzbeschreibung (Abstract):

Anisotropic samples of lyotropic liquid crystalline (LLC) phases of valine derived polyaryl acetylenes were employed as chiral alignment media for the measurement of residual dipolar couplings (RDCs) of 12 small, chiral, organic molecules. The quadrupolar splitting of the deuterium signal of CDCl₃ can be adjusted by temperature and concentration changes from 0 to 350 Hz. The LLC phases showed excellent orienting properties for all analytes bearing various functional groups. The precise extraction of RDCs in the range of up to ±30 Hz from F2‐coupled HSQC spectra was possible. Additionally, the chiral environment led to diastereomorphous interactions with the enantiomers of chiral analytes leading to two different sets of RDCs. This differential order effect was particularly pronounced with H‐bond donors like alcohols and 2° amines.

Freie Schlagworte: computational chemistry, enantiodifferentiation, lyotropic liquid crystalline phases, NMR spectroscopy, polyacetylenes, residual dipolar couplings
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Special Issue: NMR of natural products

Sachgruppe der Dewey Dezimalklassifikatin (DDC): 500 Naturwissenschaften und Mathematik > 540 Chemie
Fachbereich(e)/-gebiet(e): 07 Fachbereich Chemie
07 Fachbereich Chemie > Clemens-Schöpf-Institut
07 Fachbereich Chemie > Clemens-Schöpf-Institut > Fachgebiet Organische Chemie
Hinterlegungsdatum: 31 Jan 2024 07:39
Letzte Änderung: 31 Jan 2024 07:39
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