Synthesis and Preferred All-syn Conformation of C3-Symmetrical N-(Hetero)arylmethyl Triindoles
✍ Scribed by Eva M. García-Frutos; Berta Gómez-Lor; Ángeles Monge; Enrique Gutiérrez-Puebla; Ibon Alkorta; José Elguero
- Book ID
- 102795043
- Publisher
- John Wiley and Sons
- Year
- 2008
- Tongue
- English
- Weight
- 510 KB
- Volume
- 14
- Category
- Article
- ISSN
- 0947-6539
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✦ Synopsis
Abstract
A new series of C~3~‐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 C~3~‐symmetric dimeric cagelike 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 NCH~2~ bond.