Chiral anion recognition by a ureido-thiacalix[4]arene ligand immobilized in the 1,3-alternate conformation

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F60461373%3A22310%2F15%3A43900021" target="_blank" >RIV/60461373:22310/15:43900021 - isvavai.cz</a>

Nalezeny alternativní kódy

RIV/67985858:_____/15:00440911

Výsledek na webu

<a href="http://dx.doi.org/10.1039/c4nj01956c" target="_blank" >http://dx.doi.org/10.1039/c4nj01956c</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1039/c4nj01956c" target="_blank" >10.1039/c4nj01956c</a>

Jazyk výsledku

angličtina

Název v původním jazyce

Chiral anion recognition by a ureido-thiacalix[4]arene ligand immobilized in the 1,3-alternate conformation

Popis výsledku v původním jazyce

While all the alkylation methods commonly used in the chemistry of classical calixarenes failed, tetranitrothiacalix[4] arene was easily alkylated using various alcohols under Mitsunobu reaction conditions. The products thus obtained were immobilized inthe 1,3-alternate conformation as suggested by H-1 NMR and proven unequivocally by X-ray analysis. The introduction of chiral alkyl substituents into the lower rim of thiacalixarene gave us an opportunity to form well-preorganized ureido cavities on bothsites of the system. As revealed by H-1 NMR titration experiments, such compounds were capable of chiral anion recognition even in DMSO-d(6) which is a highly competitive solvent towards hydrogen bonding interactions. The highest chiral discrimination was achieved for free serine with a selectivity factor of 3.13 for the D-isomer

Název v anglickém jazyce

Chiral anion recognition by a ureido-thiacalix[4]arene ligand immobilized in the 1,3-alternate conformation

Popis výsledku anglicky

While all the alkylation methods commonly used in the chemistry of classical calixarenes failed, tetranitrothiacalix[4] arene was easily alkylated using various alcohols under Mitsunobu reaction conditions. The products thus obtained were immobilized inthe 1,3-alternate conformation as suggested by H-1 NMR and proven unequivocally by X-ray analysis. The introduction of chiral alkyl substituents into the lower rim of thiacalixarene gave us an opportunity to form well-preorganized ureido cavities on bothsites of the system. As revealed by H-1 NMR titration experiments, such compounds were capable of chiral anion recognition even in DMSO-d(6) which is a highly competitive solvent towards hydrogen bonding interactions. The highest chiral discrimination was achieved for free serine with a selectivity factor of 3.13 for the D-isomer

Druh

J_x - Nezařazeno - Článek v odborném periodiku (Jimp, Jsc a Jost)

CEP obor

CC - Organická chemie

OECD FORD obor

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Projekt

<a href="/cs/project/GAP207%2F12%2F2027" target="_blank" >GAP207/12/2027: Syntéza a využití inherentně chirálních calixarenů</a><br>

Návaznosti

P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)

Rok uplatnění

2015

Kód důvěrnosti údajů

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Název periodika

New Journal of Chemistry

ISSN

1144-0546

e-ISSN

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Svazek periodika

39

Číslo periodika v rámci svazku

2

Stát vydavatele periodika

GB - Spojené království Velké Británie a Severního Irska

Počet stran výsledku

8

Strana od-do

1382-1389

Kód UT WoS článku

000349222800076

EID výsledku v databázi Scopus

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