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Pregled bibliografske jedinice broj: 949641

Determination of the Absolute Configuration of (S )-N -(1-Aryl-allyl)-3, 5-dinitrobenzamides and Their Elution Order on Brush-Type Chiral Stationary Phases


Knežević, Anamarija; Novak, Jurica; Pescitelli, Gennaro; Vinković, Vladimir
Determination of the Absolute Configuration of (S )-N -(1-Aryl-allyl)-3, 5-dinitrobenzamides and Their Elution Order on Brush-Type Chiral Stationary Phases // European journal of organic chemistry, 2018 (2018), 19; 3982-3991 doi:10.1002/ejoc.201800346 (međunarodna recenzija, članak, znanstveni)


CROSBI ID: 949641 Za ispravke kontaktirajte CROSBI podršku putem web obrasca

Naslov
Determination of the Absolute Configuration of (S )-N -(1-Aryl-allyl)-3, 5-dinitrobenzamides and Their Elution Order on Brush-Type Chiral Stationary Phases

Autori
Knežević, Anamarija ; Novak, Jurica ; Pescitelli, Gennaro ; Vinković, Vladimir

Izvornik
European journal of organic chemistry (1434-193X) 2018 (2018), 19; 3982-3991

Vrsta, podvrsta i kategorija rada
Radovi u časopisima, članak, znanstveni

Ključne riječi
Ab initio calculations ; Chiral resolution ; Circular dichroism ; Configuration determination ; Liquid chromatography

Sažetak
A series of ten enantiomerically pure (S)‐N‐(1‐ aryl‐allyl)‐3, 5‐dinitrobenzamides (S‐DNBs) was prepared using enzymatic resolution and chiral chromatography. Enzymatic resolution of corresponding 1‐aryl‐allylamines using Candida antarctica lipase B (CaLB) was efficient for amines with no steric hindrance near the stereogenic center and S‐DNB amides were prepared by acylation of the obtained S‐amine. When steric effects interrupted enzymatic resolution, racemic DNB amides were resolved using a brush‐type chiral column (CSP‐A) developed in our laboratory. Previously reported behavior of CaLB in kinetic resolution of amines was considered a starting point for the determination of absolute configuration (AC). The AC of prepared S‐DNB amides was anticipated using the elution order of prepared DNB amides on CSP‐A and commercial Whelk‐O1 columns and comparison with DNB amides obtained after acylation of (S)‐amines. The comparison between experimental electronic circular dichroism (ECD) spectra with those obtained by conformational analysis and ECD calculations of representative compounds allowed us to verify the AC of prepared DNB amides.

Izvorni jezik
Engleski

Znanstvena područja
Kemija



POVEZANOST RADA


Projekti:
HRZZ-IP-2016-06-1142 - Svjetlo na molekulama: istraživanje spregnute elektronske i nuklearne dinamike (LightMol) (Došlić, Nađa, HRZZ - 2016-06) ( POIROT)

Ustanove:
Institut "Ruđer Bošković", Zagreb

Poveznice na cjeloviti tekst rada:

doi onlinelibrary.wiley.com

Citiraj ovu publikaciju:

Knežević, Anamarija; Novak, Jurica; Pescitelli, Gennaro; Vinković, Vladimir
Determination of the Absolute Configuration of (S )-N -(1-Aryl-allyl)-3, 5-dinitrobenzamides and Their Elution Order on Brush-Type Chiral Stationary Phases // European journal of organic chemistry, 2018 (2018), 19; 3982-3991 doi:10.1002/ejoc.201800346 (međunarodna recenzija, članak, znanstveni)
Knežević, A., Novak, J., Pescitelli, G. & Vinković, V. (2018) Determination of the Absolute Configuration of (S )-N -(1-Aryl-allyl)-3, 5-dinitrobenzamides and Their Elution Order on Brush-Type Chiral Stationary Phases. European journal of organic chemistry, 2018 (19), 3982-3991 doi:10.1002/ejoc.201800346.
@article{article, author = {Kne\v{z}evi\'{c}, Anamarija and Novak, Jurica and Pescitelli, Gennaro and Vinkovi\'{c}, Vladimir}, year = {2018}, pages = {3982-3991}, DOI = {10.1002/ejoc.201800346}, keywords = {Ab initio calculations, Chiral resolution, Circular dichroism, Configuration determination, Liquid chromatography}, journal = {European journal of organic chemistry}, doi = {10.1002/ejoc.201800346}, volume = {2018}, number = {19}, issn = {1434-193X}, title = {Determination of the Absolute Configuration of (S )-N -(1-Aryl-allyl)-3, 5-dinitrobenzamides and Their Elution Order on Brush-Type Chiral Stationary Phases}, keyword = {Ab initio calculations, Chiral resolution, Circular dichroism, Configuration determination, Liquid chromatography} }
@article{article, author = {Kne\v{z}evi\'{c}, Anamarija and Novak, Jurica and Pescitelli, Gennaro and Vinkovi\'{c}, Vladimir}, year = {2018}, pages = {3982-3991}, DOI = {10.1002/ejoc.201800346}, keywords = {Ab initio calculations, Chiral resolution, Circular dichroism, Configuration determination, Liquid chromatography}, journal = {European journal of organic chemistry}, doi = {10.1002/ejoc.201800346}, volume = {2018}, number = {19}, issn = {1434-193X}, title = {Determination of the Absolute Configuration of (S )-N -(1-Aryl-allyl)-3, 5-dinitrobenzamides and Their Elution Order on Brush-Type Chiral Stationary Phases}, keyword = {Ab initio calculations, Chiral resolution, Circular dichroism, Configuration determination, Liquid chromatography} }

Časopis indeksira:


  • Current Contents Connect (CCC)
  • Web of Science Core Collection (WoSCC)
    • Science Citation Index Expanded (SCI-EXP)
    • Arts & Humanities Citation Index (A&HCI)
    • SCI-EXP, SSCI i/ili A&HCI
  • Scopus


Citati:





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