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Synthesis and evaluation of chiral stationary phases containing N-(1-arilpropil)-3, 5-dinitrobenzamide selector

Knežević, Anamarija (2013) Synthesis and evaluation of chiral stationary phases containing N-(1-arilpropil)-3, 5-dinitrobenzamide selector. Doctoral thesis, Sveučilište u Zagrebu, Prirodoslovno-matematički fakultet.

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A set of nine new brush-type chiral stationary phases (CSPs) which possess fewer achiral adsorption sites was synthesized. Prepared CSPs differ in aromatic units directly linked to the chiral center. Chiral selector, the N-(1-arylpropyl)-3,5-dinitrobenzamide unit, has all the properties of a good selector – it is rigid and contains a strong π-accepting 3,5-dinitrobenzoyl and a strong π-donating aromatic group. The key intermediates in the synthesis are enantiomericaly pure allyl aryl amines prepared by enzymatic resolution. Racemic amines were obtained by Overman rearrangement of acyclic imidates. Imidates were prepared from the corresponding alcohols which were synthesized from available aldehydes in a Knoevenagel reaction followed by ester reduction. The method for binding the chiral selector to silica gel was selected in such a manner that additional polar groups were not introduced. Thirty various racemic analytes were used to evaluate the prepared CSPs. The results were compared and the influence of the aromatic unit on enantioseparation of the analytes was demonstrated. Chromatographic evaluation showed that the new CSPs separate enantiomers of a wide range of compounds and the best results demonstrate CSPs that contain a selector with the naphthyl substituent.

Item Type: Thesis (Doctoral thesis)
Uncontrolled Keywords: aromatic interactions ; brush-type chiral stationary phases ; enzymatic resolution of amines ; Knoevenagel reaction ; Overman rearrangement
Subjects: NATURAL SCIENCES > Chemistry
NATURAL SCIENCES > Chemistry > Organic Chemistry
Divisions: Division of Organic Chemistry and Biochemistry
Project titleProject leaderProject codeProject type
Kiralni organski materijali – sintetska, strukturna i funkcionalna istraživanja-Vladimir Vinković098-0982904-2910MZOS
Depositing User: Anamarija Knežević
Date Deposited: 25 Oct 2017 11:28

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