Reasons Why Aldehydes Do Not Generally Participate in Cucurbit[n]uril Forming Reactions

Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216224%3A14310%2F10%3A00048650" target="_blank" >RIV/00216224:14310/10:00048650 - isvavai.cz</a>
Result on the web
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DOI - Digital Object Identifier
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Result language
angličtina
Original language name
Reasons Why Aldehydes Do Not Generally Participate in Cucurbit[n]uril Forming Reactions
Original language description
The reaction of substituted glycolurils or a glycoluril dimer with a dialdehyde (o_phthalaldehyde) delivers S_shaped dimers and an S-shaped tetramer selectively. A combination of X_ray crystallography, PM3 calculations, and product resubmission experiments establish that the S_shaped isomers are thermodynamically more stable than the C_shaped diastereomers which we attribute to the conformational preferences of the newly formed benzo bicyclo[3.3.2]decane ring system. The preferential formation of S_shaped subunits is one reason why o_phthalaldehyde and possibly other aldehydes do not usually participate in CB[n] forming reactions. We also present evidence that points toward an equilibrium between glycoluril monomer + phthalaldehyde and S_shaped dimer +water that responds to concentration over the 1_50 mM range. This result suggests a second reason, insufficient reactivity (e.g., low equilibrium constant), why o-phthalaldehyde and possibly other aldehydes do not participate in CB[n] fo
Czech name
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Czech description
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Type
J<sub>x</sub> - Unclassified - Peer-reviewed scientific article (Jimp, Jsc and Jost)
CEP classification
CC - Organic chemistry
OECD FORD branch
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Project
<a href="/en/project/GP203%2F07%2FP382" target="_blank" >GP203/07/P382: New cucurbit[n]uril derivatives</a><br>
Continuities
P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)

Publication year
2010
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

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