Generation of Cryptophanes in Water by Disulfide Bridge Formation

Result code in 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>
Result on the web
<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>

Result language
angličtina
Original language name
Generation of Cryptophanes in Water by Disulfide Bridge Formation
Original language description
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
Czech name
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Czech description
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Type
J<sub>imp</sub> - Article in a specialist periodical, which is included in the Web of Science database
CEP classification
—
OECD FORD branch
10401 - Organic chemistry

Project
<a href="/en/project/7AMB14FR074" target="_blank" >7AMB14FR074: Design of novel anion receptors based on the dynamic combinatorial chemistry approach</a><br>
Continuities
P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)

Publication year
2017
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

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