N → π* interactions as a versatile tool for controlling dynamic imine chemistry in both organic and aqueous media.

ABSTRACT: The imine bond holds a prominent place in supramolecular chemistry and materials science, and one issue is the stability of imines due to their electrophilic nature. Here we introduced ortho-carboxylate groups into a series of aromatic aldehydes/imines for dictating imine dynamic covalent chemistry (DCC) through n → π* interactions, one class of widespread and yet underused non-covalent interactions. The thermodynamically stabilizing role of carboxylate-aldehyde/imine n → π* interactions in acetonitrile was elucidated by the movement of the imine exchange equilibrium and further supported by crystal analysis. Computational studies provided mechanistic insights for n → π* interactions, the strength of which can surpass that of CH hydrogen bonding and is dependent on the orientation o

SUBMITTER: Chen H 

PROVIDER: S-EPMC8157614 | biostudies-literature | 2020 Jan

REPOSITORIES: biostudies-literature