A Cationic Catechol Derivative Binds Anions in Competitive Aqueous Media.
Chem Asian J
; 19(6): e202301121, 2024 Mar 15.
Article
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| MEDLINE
| ID: mdl-38269957
ABSTRACT
A simple dihydroxy isoquinolinium molecule (3+) was prepared by a modification of a literature procedure. Interestingly, during optimisation of the synthesis a small amount of the natural product pseudopalmatine was isolated, and characterised for the first time by X-ray crystallography. Compound 3+ contains a catechol motif and positive charge on the same scaffold and was found to be a potent anion receptor, binding sulfate strongly in 8 2 d6-acetoneD2O and 7 3 d6-acetoneD2O (Ka>104 and 2,100â
M-1, respectively). Unsurprisingly, chloride binding was much weaker, even in the less polar solvent mixture 9 1 d6-acetoneD2O. The sulfate binding is remarkably strong for such a simple molecule, however anion binding studies were complicated by the tendency of the molecule to react with BPh4 - or BF4 - species during anion metathesis reactions. This gave two unusual zwitterions containing tetrahedral boronate centres, which were both characterised by X-ray crystallography.
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1
Colección:
01-internacional
Base de datos:
MEDLINE
Idioma:
En
Revista:
Chem Asian J
Año:
2024
Tipo del documento:
Article
País de afiliación:
Australia
Pais de publicación:
Alemania