Sulphonamidic Groups as Electron‐Withdrawing Units in Ureido‐Based Anion Receptors: Enhanced Anion Complexation versus Deprotonation

0525426 - ÚFCH JH 2021 RIV DE eng J - Journal Article
Salvadori, Karolína - Šimková, Ludmila - Císařová, I. - Sýkora, J. - Ludvík, Jiří - Cuřínová, P.
Sulphonamidic Groups as Electron‐Withdrawing Units in Ureido‐Based Anion Receptors: Enhanced Anion Complexation versus Deprotonation.
ChemPlusChem. Roč. 85, č. 7 (2020), s. 1401-1411. ISSN 2192-6506. E-ISSN 2192-6506
Institutional support: RVO:61388955
Keywords : anion recognition * electron-withdrawing groups * host-guest systems
OECD category: Electrochemistry (dry cells, batteries, fuel cells, corrosion metals, electrolysis)
Impact factor: 2.863, year: 2020
Method of publishing: Limited access

A sulphonamidic moiety was utilized as an electron‐withdrawing group for enhancement of anion complexation features of urea‐based receptors. A series of receptors varying in acidity of sulphonamidic and urea NH groups was synthesized and thoroughly tested. The individual complexation properties reflect deprotonation/complexation equilibrium in a given molecule as a function of the substitution. The receptors containing electron‐donating groups in conjugation to the sulphonamidic moiety showed higher association constants towards H2PO4− and carboxylate anions, while those containing electron‐withdrawing groups inclined to deprotonation of sulphonamidic NH. The deprotonation issue can be avoided by alkylation at the early step of receptor synthesis or it can be utilized for insertion of suitable groups that enable its anchoring on various substrates to form more elaborated receptor structures.

Permanent Link: http://hdl.handle.net/11104/0309573