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Synthesis and preferred all-syn conformation of C3-symmetrical N-(hetero)arylmethyl triindoles

AuthorsGarcía-Frutos, Eva M. ; Gómez-Lor, Berta ; Monge Bravo, M.ª Ángeles; Gutiérrez-Puebla, Enrique ; Alkorta, Ibon ; Elguero, José
Issue Date2008
PublisherJohn Wiley & Sons
CitationChemistry - A European Journal 14: 8555- 8561 (2008)
AbstractA new series of C3-symmetrical N-(hetero)arylmethyl triindoles has been synthesized in a straightforward procedure. The structure and conformation in the solid state have been determined for three derivatives (3, 4, and 6) by X-ray crystallographic analysis. In all three cases, the molecules adopt a tripodal conformation with all of the flexible arms directed towards the same side, thereby delimiting an inner cavity. Compound 6 crystallizes and forms C3-symmetric dimeric cage-like complexes. Guest molecules of chloroform and water are confined within the resulting cavities with stabilization by different intermolecular interactions; this highlights the potential of these compounds in the construction of supramolecular systems. A computational analysis has been performed to predict the most stable conformers. As a general trend, a preference for a conformation with all branches directed to the same side has been predicted. Comparison between theoretical and experimental results indicates that the computational level selected for the present study, B3LYP/6-31G*, is able to reproduce both the minimum energy conformations and the rotation barriers about the N-CH2 bond. © 2008 Wiley-VCH Verlag GmbH & Co. KGaA.
Identifiersdoi: 10.1002/chem.200800911
issn: 0947-6539
e-issn: 1521-3765
Appears in Collections:(IQM) Artículos
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