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FEATURED COVER
Cover Image, Volume 36, Issue 6
- First Published: 30 July 2024

The cover image is based on the Research Article Self-Assembled Chiral Film Based on Melanin Polymers by Massimiliano Gaeta et al., https://doi.org/10.1002/chir.23695.
ISSUE INFORMATION
RESEARCH ARTICLES
Graph-theoretical chirality measure and chirality–property relations for chemical structures with multiscale mirror asymmetries
- First Published: 10 June 2024

Chirality measures can be exceptionally difficult to calculate and reveal weak, if any, correlations with physical, chemical, and biological properties of chemical structures. Applying the concept of torsion in the framework of discrete mathematics to graph representations of molecular and nanoscale helicoids, we show that graph-theoretical chirality measure (GTC) addresses long-standing fundamental problems and practical limitations of prior quantifiers of mirror asymmetry. GTC calculated for molecular, nanoscale, mesoscale, and microscale structures produce chirality vectors comprehensively characterizing hierarchical levels of chemical asymmetry. The chiroptical activity of helicoids reveals consistent polarity-discerning relations to scale specific components of GTC chirality vectors.
Determination of N-centered stereochemistry in N22-methylated chlorophyll-a derivatives and their epimer-dependent optical spectra
- First Published: 05 June 2024

An N-centered epimeric mixture of chlorophyll-a derivatives methylated at the inner nitrogen atom was separated by RP-HPLC. CD spectroscopic analyses of the epimerically pure N22-methyl-chlorins revealed that the minor first-eluted and major second-eluted stereoisomers were (22S)- and (22R)-configurations, respectively. Their visible absorption and CD spectra in solution were dependent on the N22-stereochemistry, but the epimer-dependent spectral changes were independent of the peripheral C3-substituents (R3).
Enantioselective liquid–liquid extraction of 2-cyclohexylmandelic acid enantiomers using chiral ionic liquids
- First Published: 28 May 2024

A multistage stereoselective liquid–liquid extraction system coupled with imidazolium cations and amino acid-derived anions was established for racemic separation of 2-cyclohexylmandelic acid. The enantiomeric excess (e.e.) of 40.6% was obtained for 2-cyclohexylmandelic acid in three-stage operational liquid–liquid extraction system.
TUTORIALS
Counting the truxillines—11 or more, the question is now
- First Published: 21 May 2024

Truxillines are a group of tropane alkaloids present in coca leaves. Contrary to the statements repeatedly presented in the literature, here we show that, in fact, a total of 15 truxillines exist, which can be divided in two structurally isomeric groups—five mutually diastereomeric truxillates and 10 mutually diastereomeric truxinates.