Supramolecularly assisted synthesis of chiral tripodal imidazolium compounds
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Other documents of the author: Valls Ten, Adriana; Altava, Belen; Burguete, M. Isabel; Escorihuela, Jorge; Martí-Centelles, Vicente; Luis, Santiago V.
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comunitat-uji-handle2:10234/7053
comunitat-uji-handle3:10234/8639
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Title
Supramolecularly assisted synthesis of chiral tripodal imidazolium compoundsAuthor (s)
Date
2019Publisher
Royal Society of ChemistryISSN
2052-4110; 2052-4129Bibliographic citation
Org. Chem. Front., 2019, 6, 1214.Type
info:eu-repo/semantics/articleVersion
info:eu-repo/semantics/acceptedVersionAbstract
A strong preference for the formation of tripodal systems over the related monotopic and ditopic compounds is observed for the reaction between tris(halomethyl)benzenes and imidazoles derived from
amino acids and ... [+]
A strong preference for the formation of tripodal systems over the related monotopic and ditopic compounds is observed for the reaction between tris(halomethyl)benzenes and imidazoles derived from
amino acids and containing an amide fragment. This preference allows the formation of the tripodal
derivative as the major product even when an equimolar mixture of the tris(halomethyl)benzene and the
imidazole is reacted (1 : 1 ratio instead of the stoichiometric 1 : 3 ratio). The reactions were monitored
using 1
H NMR spectroscopy and ESI mass spectrometry and kinetically characterized. Computational
studies were also performed in order to rationalize the observed preference of the tri-substituted
product. The results reveal the existence of well-defined supramolecular interactions between the imidazolium groups and the reacting imidazoles that facilitate the formation of the multitopic systems once the
first imidazolium group is formed. Analysis of the different structural components shows that the presence
of the amide group from the amino acid moiety is the key structural requirement for such supramolecular
assistance to take place. The preorganization of the supramolecular intermediates formed through hydrogen bonding interactions involving amide-NH fragments in imidazoles and bromide anions in imidazolium
groups seems to be also present at the corresponding TSs, decreasing the associated energy barriers. [-]
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Organic Chemistry Frontiers, 2019, 6.Investigation project
CTQ2015-68429-R ; PROMETEO/2016/071Rights
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