Open AccessExamination of the Dynamic Covalent Chemistry of [2 + 3]-Imine Cages
Author(s) -
Tobias H. G. Schick,
Frank Röminger,
Michael Mastalerz
Publication year - 2020
Publication title -
journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.2
H-Index - 228
eISSN - 1520-6904
pISSN - 0022-3263
DOI - 10.1021/acs.joc.0c01887
Subject(s) - imine , dynamic covalent chemistry , covalent bond , chemistry , cage , deuterium , block (permutation group theory) , computational chemistry , molecule , organic chemistry , supramolecular chemistry , catalysis , atomic physics , mathematics , geometry , physics , combinatorics
The synthesis of shape-persistent organic cage compounds by the formation of imine bonds opens the possibility to realize cages of different sizes, geometries, topologies, and functions. It is generally assumed that the imine bond is rather chemically labile allowing a self-correction mechanism until thermodynamic equilibrium is reached, which is often the case if a cage is formed. However, there are some contradictory experimental data to this assumption. To get a deeper insight into the imine bond dynamics of covalent organic cages, we studied the formation and exchange of both dialdehydes and triamines of two different [2 + 3] imine cages with the aid of a deuterated dialdehyde molecular building block.