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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