| MA, Da, Zuzana GARGULÁKOVÁ, Peter Y. ZAVALIJT, Vladimír ŠINDELÁŘ a Lyle ISAACS. Reasons Why Aldehydes Do Not Generally Participate in Cucurbit[n]uril Forming Reactions. Journal of Organic Chemistry. 2010, roč. 75, č. 9, s. 2934-2941, 13 s. ISSN 0022-3263. |
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@article{883648,
author = {Ma, Da and Garguláková, Zuzana and Zavalijt, Peter Y. and Šindelář, Vladimír and Isaacs, Lyle},
article_number = {9},
keywords = {cucurbiturils; macrocycles},
language = {eng},
issn = {0022-3263},
journal = {Journal of Organic Chemistry},
title = {Reasons Why Aldehydes Do Not Generally Participate in Cucurbit[n]uril Forming Reactions},
url = {http://pubs.acs.org/doi/abs/10.1021/jo100186q},
volume = {75},
year = {2010}
}
TY - JOUR
ID - 883648
AU - Ma, Da - Garguláková, Zuzana - Zavalijt, Peter Y. - Šindelář, Vladimír - Isaacs, Lyle
PY - 2010
TI - Reasons Why Aldehydes Do Not Generally Participate in Cucurbit[n]uril Forming Reactions
JF - Journal of Organic Chemistry
VL - 75
IS - 9
SP - 2934-2941
EP - 2934-2941
SN - 00223263
KW - cucurbiturils
KW - macrocycles
UR - http://pubs.acs.org/doi/abs/10.1021/jo100186q
N2 - 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] forming reactions. Delineation of the reasons why some aldehydes fail in these reactions is the first step toward devising methods to overcome these limitations.
ER -
MA, Da, Zuzana GARGULÁKOVÁ, Peter Y. ZAVALIJT, Vladimír ŠINDELÁŘ a Lyle ISAACS. Reasons Why Aldehydes Do Not Generally Participate in Cucurbit[n]uril Forming Reactions. \textit{Journal of Organic Chemistry}. 2010, roč.~75, č.~9, s.~2934-2941, 13 s. ISSN~0022-3263.
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