Premium
A Chiral “Frozen” Hydrogen Bonding in C 4 ‐Symmetric Inherently Chiral Resorcin[4]arenes: NMR, X‐ray, Circular Dichroism, and Theoretical Study (Eur. J. Org. Chem. 18/2008)
Author(s) -
Kuberski Bogumił,
Pecul Magdalena,
Szumna Agnieszka
Publication year - 2008
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200890045
Subject(s) - chemistry , hydrogen bond , intramolecular force , diastereomer , crystallography , molecule , resorcinarene , circular dichroism , chirality (physics) , stereochemistry , symmetry breaking , organic chemistry , chiral symmetry breaking , nambu–jona lasinio model , physics , quantum mechanics
Abstract The cover picture shows the X‐ray structure of C C 4 ‐symmetric, chiral resorcinarene substituted with L ‐leucine at the upper rim. The molecule is held in the inherently chiral conformation (resembling a chiral C C 4 ‐symmetric propeller) by means of twelve intramolecular hydrogen bonds. The seams of hydrogen bonds can be directed in one particular direction because of diastereomeric preferences. The determination of the direction of the hydrogen‐bonding seam and the correlation with CD spectra is discussed in the article by A. Szumna et al. on p. 3069 ff.