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Valine derived poly (acetylenes) as versatile chiral lyotropic liquid crystalline alignment media for RDC‐based structure elucidations
Author(s) -
Krupp Alexis,
Noll Markus,
Reggelin Michael
Publication year - 2021
Publication title -
magnetic resonance in chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.483
H-Index - 72
eISSN - 1097-458X
pISSN - 0749-1581
DOI - 10.1002/mrc.5003
Subject(s) - chemistry , lyotropic , deuterium , enantiomer , liquid crystal , molecule , chirality (physics) , anisotropy , dipole , residual dipolar coupling , analytical chemistry (journal) , organic chemistry , liquid crystalline , phase (matter) , chiral symmetry breaking , optics , physics , quantum mechanics , quark , nambu–jona lasinio model
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 CDCl 3 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.