+ Site Statistics
+ Search Articles
+ PDF Full Text Service
How our service works
Request PDF Full Text
+ Follow Us
Follow on Facebook
Follow on Twitter
Follow on LinkedIn
+ Subscribe to Site Feeds
Most Shared
PDF Full Text
+ Translate
+ Recently Requested

A new chiral selector based on trans-acenaphthen-1,2-dicarboxylic acid

A new chiral selector based on trans-acenaphthen-1,2-dicarboxylic acid

Enantiomer 5(5): 451-455

The chiral selectors (R,R)- and (S,S)-trans-acenaphthen-1,2-dicarboxylic acid bis-allylamide have been synthesized and characterized. The route to the selectors involved synthesis of the trans-dicarboxylic acid via sodiation and carbonation of acenaphthylene, followed by reaction of the bis-acid chloride with allylamine. The racemic bis-allylamide derivative was resolved into its enantiomers by preparative liquid chromatography. The chiral discrimination effect from the (R,R)-selector in the 1H-NMR spectra of a mixture of the enantiomers of O,O'-dibenzoyltartaric acid was studied as a function of temperature. Due to certain ambiguities in the literature concerning the absolute configuration of the (+)-rotating trans-acenaphthen-1,2-dicarboxylic acid, its brucine salt was subjected to X-ray crystallography. This showed the (+)-form to be of (R,R)-configuration.

Please choose payment method:

(PDF emailed within 1 workday: $29.90)

Accession: 045079361

Download citation: RISBibTeXText

PMID: 11143809

Related references

Preparation and evaluation of a new synthetic polymeric chiral stationary phase for HPLC based on the trans-9,10-dihydro-9,10-ethanoanthracene-(11S,12S)-11,12-dicarboxylic acid bis-4-vinylphenylamide monomer. Analytical and Bioanalytical Chemistry 387(8): 2681-2697, 2007

Preparation of a New Chiral Stationary Phase Based on Macrocyclic Amide Chiral Selector for the Liquid Chromatographic Chiral Separations. Chirality 28(3): 253-258, 2016

Trans-selective asymmetric aziridination of diazoacetamides and N-Boc imines catalyzed by axially chiral dicarboxylic acid. Journal of the American Chemical Society 130(44): 14380-1, 2008

Three-dimensional hydrogen-bonded structures in the guanidinium salts of the monocyclic dicarboxylic acids rac-trans-cyclohexane-1,2-dicarboxylic acid (2:1, anhydrous), isophthalic acid (1:1, monohydrate) and terephthalic acid (2:1, trihydrate). Acta Crystallographica. Section C, Crystal Structure Communications 66(Pt 12): O575-O580, 2011

Direct chiral resolution of tartaric acid in food products by ligand exchange capillary electrophoresis using copper(II)-D-quinic acid as a chiral selector. Journal of Chromatography, A 932(1/2): 139-143, 2001

Direct chiral resolution of malic acid in apple juice by ligand-exchange capillary electrophoresis using copper(II)-L-tartaric acid as a chiral selector. Electrophoresis 22(15): 3286-3290, 2001

Evaluation of dalbavancin as chiral selector for HPLC and comparison with teicoplanin-based chiral stationary phases. Chirality 22(5): 495-513, 2010

Novel chiral selector based on mefloquine--a comparative NMR study to elucidate intermolecular interactions with acidic chiral selectands. Chirality 24(11): 936-943, 2012

Enantioseparation of amlodipine maleate by capillary electrophoresis using colominic acid as a chiral selector and the mechanism of chiral recognition. Yao Xue Xue Bao 39(9): 734-737, 2004

Chiral separation of the clinically important compounds fucose and pipecolic acid using CE: determination of the most effective chiral selector. Chirality 25(9): 556-560, 2014

Direct chiral resolution of tiaprofenic acid in pharmaceutical formulations by capillary zone electrophoresis using cyclodextrins as chiral selector. Journal of Capillary Electrophoresis 2(5): 213-217, 1995

Chiral counter-current chromatography of gemifloxacin guided by capillary electrophoresis using (+)-(18-crown-6)-tetracarboxylic acid as a chiral selector. Journal of Chromatography. A 1045(1-2): 119-124, 2004

Chiral discrimination of quinine and quinidine based on notable room temperature phosphorescence lifetime differences with gamma-cyclodextrin as chiral selector. Talanta 73(5): 938-942, 2007

Evaluation of silica gel-based brush type chiral cation exchangers with -N- tyrosine as chiral selector Attempt to interpret the discouraging results. Journal of Chromatography A 694(1): 151-161, 1995