Hydrogen bond formation may enhance RDC-based discrimination of enantiomers

Bibliographische Detailangaben
Veröffentlicht in:	Magnetic resonance in chemistry : MRC. - 1985. - 62(2024), 9 vom: 01. Aug., Seite 639-647
1. Verfasser:	Sager, Emine (VerfasserIn)
Weitere Verfasser:	Tzvetkova, Pavleta, Lingel, Andreas, Gossert, Alvar D, Luy, Burkhard
Format:	Online-Aufsatz
Sprache:	English
Veröffentlicht:	2024
Zugriff auf das übergeordnete Werk:	Magnetic resonance in chemistry : MRC
Schlagworte:	Journal Article PBLG hydrogen bonding partial alignment residual dipolar couplings solute medium interaction

Beschreibung
Zusammenfassung:	© 2024 The Authors. Magnetic Resonance in Chemistry published by John Wiley & Sons Ltd. The distinction of enantiomers based on residual anisotropic parameters obtained by alignment in chiral poly-γ-benzyl-L-glutamate (PBLG) is among the strongest in high-resolution NMR spectroscopy. However, large variations in enantiodifferentiation among different solutes are frequently observed. One hypothesis is that the formation of hydrogen bonds between solute and PBLG is important for the distinction of enantiomers. With a small set of three almost spherical enantiomeric pairs, for which 1DCH residual dipolar couplings are measured, we address this issue in a systematic way: borneol contains a single functional group that can act as a hydrogen bond donor, camphor has a single group that may act as a hydrogen bond acceptor, and quinuclidinol can act as both hydrogen bond donor and acceptor. The results are unambiguous: although camphor shows low enantiodifferentiation with PBLG and alignment that can be predicted well by the purely steric TRAMITE approach, the distinction of enantiomers for the other enantiomeric pairs is significantly higher with alignment properties that must involve a specific interaction in addition to steric alignment
Beschreibung:	Date Revised 02.08.2024 published: Print-Electronic Citation Status PubMed-not-MEDLINE
ISSN:	1097-458X
DOI:	10.1002/mrc.5448