Issue 23, 2021, Issue in Progress

Rationalization of chirality transfer and fast conformational changes in a tris(2-pyridylmethyl)amine-based cage

Abstract

The key features that govern the chirality transfer in a structurally contracted covalent cage, consisting of a northern chiral cyclotriveratrylene (CTV) connected to a southern tris(2-pyridyl-methyl)amine (TPA) unit by three methyl bridges, are described. The preferential orientation of the propeller arrangement of TPA is dictated by its compact structure, with an arm of the TPA unit pointing inside the cage, together with the relative positioning of the three pyridines regarding the chiral CTV cap. The diastereomers with P/P (or M/M) configurations for the CTV and TPA units adopt eclipsed structures and were found to be more stable by 40 kJ mol−1 than the P/M (or M/P) diastereomer which displays a staggered arrangement. The existence of isomerization pathways between isomers of the cage with low energy barriers (38 kJ mol−1) accounts for the 1H-NMR signal, which is consistent with an averaged C3 structure.

Graphical abstract: Rationalization of chirality transfer and fast conformational changes in a tris(2-pyridylmethyl)amine-based cage

Supplementary files

Article information

Article type
Paper
Submitted
05 Mar 2021
Accepted
01 Apr 2021
First published
13 Apr 2021
This article is Open Access
Creative Commons BY-NC license

RSC Adv., 2021,11, 13763-13768

Rationalization of chirality transfer and fast conformational changes in a tris(2-pyridylmethyl)amine-based cage

G. Qiu, D. E. Khatmi, A. Martinez and P. Nava, RSC Adv., 2021, 11, 13763 DOI: 10.1039/D1RA01761F

This article is licensed under a Creative Commons Attribution-NonCommercial 3.0 Unported Licence. You can use material from this article in other publications, without requesting further permission from the RSC, provided that the correct acknowledgement is given and it is not used for commercial purposes.

To request permission to reproduce material from this article in a commercial publication, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party commercial publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements