Generation of Cryptophanes in Water by Disulfide Bridge Formation
Identifikátory výsledku
Kód výsledku v IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F60461373%3A22310%2F17%3A43914899" target="_blank" >RIV/60461373:22310/17:43914899 - isvavai.cz</a>
Výsledek na webu
<a href="https://chemistry-europe.onlinelibrary.wiley.com/doi/full/10.1002/ejoc.201700537" target="_blank" >https://chemistry-europe.onlinelibrary.wiley.com/doi/full/10.1002/ejoc.201700537</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1002/ejoc.201700537" target="_blank" >10.1002/ejoc.201700537</a>
Alternativní jazyky
Jazyk výsledku
angličtina
Název v původním jazyce
Generation of Cryptophanes in Water by Disulfide Bridge Formation
Popis výsledku v původním jazyce
Cryptophanes are receptors consisting of two bridging concave cyclotribenzylene (CTB) subunits. The formation of cryptophanes in basic aqueous solutions (0.1 M MOD; M = Li, Na, K, and Cs) by disulfide bridge formation has been investigated. Two original CTBs, 1H(6) and 2H(6), derived from cyclotriphenolene through the introduction of mercaptomethyl and mercapto substituents, respectively, were synthesized. Cryptophane formation by slow oxygenation of 1(6-) was observed only in the presence of Me4N+ as template, which yielded the diastereomeric forms in a ratio of around 82:18. By contrast, the rigid CTB 2H(6) yielded a cryptophane stereoselectively without a template. Interestingly, air oxidation of a 1:1 mixture of 1(6-) and 2(6-) in the presence of Me4N+ (0.5-1 equiv./1(6-)) in 0.1 m LiOD led to the exclusive formation of the cryptophane complex [(1.1)(6-)superset of+NMe4], (2.2)(6-) being formed only in very minor amounts. No mixed species were detected in the reaction mixtures. The stabilities of the diastereomers of the protonated cryptophanes were calculated in the gas phase by DFT at the omega B97XD 6-311G(d,p) level of theory
Název v anglickém jazyce
Generation of Cryptophanes in Water by Disulfide Bridge Formation
Popis výsledku anglicky
Cryptophanes are receptors consisting of two bridging concave cyclotribenzylene (CTB) subunits. The formation of cryptophanes in basic aqueous solutions (0.1 M MOD; M = Li, Na, K, and Cs) by disulfide bridge formation has been investigated. Two original CTBs, 1H(6) and 2H(6), derived from cyclotriphenolene through the introduction of mercaptomethyl and mercapto substituents, respectively, were synthesized. Cryptophane formation by slow oxygenation of 1(6-) was observed only in the presence of Me4N+ as template, which yielded the diastereomeric forms in a ratio of around 82:18. By contrast, the rigid CTB 2H(6) yielded a cryptophane stereoselectively without a template. Interestingly, air oxidation of a 1:1 mixture of 1(6-) and 2(6-) in the presence of Me4N+ (0.5-1 equiv./1(6-)) in 0.1 m LiOD led to the exclusive formation of the cryptophane complex [(1.1)(6-)superset of+NMe4], (2.2)(6-) being formed only in very minor amounts. No mixed species were detected in the reaction mixtures. The stabilities of the diastereomers of the protonated cryptophanes were calculated in the gas phase by DFT at the omega B97XD 6-311G(d,p) level of theory
Klasifikace
Druh
J<sub>imp</sub> - Článek v periodiku v databázi Web of Science
CEP obor
—
OECD FORD obor
10401 - Organic chemistry
Návaznosti výsledku
Projekt
<a href="/cs/project/7AMB14FR074" target="_blank" >7AMB14FR074: Design nových aniontových receptorů založených na využití dynamické kombinatorní chemie</a><br>
Návaznosti
P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)
Ostatní
Rok uplatnění
2017
Kód důvěrnosti údajů
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů
Údaje specifické pro druh výsledku
Název periodika
European Journal of Organic Chemistry
ISSN
1434-193X
e-ISSN
—
Svazek periodika
2017
Číslo periodika v rámci svazku
26
Stát vydavatele periodika
DE - Spolková republika Německo
Počet stran výsledku
17
Strana od-do
3795-3811
Kód UT WoS článku
000405130200008
EID výsledku v databázi Scopus
2-s2.0-85024109767