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

0525211 - ÚCHP 2021 RIV DE eng J - Journal Article
Salvadori, Karolína - Šimková, L. - Císařová, I. - Sýkora, Jan - Ludvík, J. - Cuřínová, Petra
Sulphonamidic Groups as Electron‐Withdrawing Units in Ureido‐Based Anion Receptors: Enhanced Anion Complexation versus Deprotonationl.
ChemPlusChem. Roč. 85, č. 7 (2020), s. 1401-1411. ISSN 2192-6506. E-ISSN 2192-6506
R&D Projects: GA ČR(CZ) GA20-07833S
Institutional support: RVO:67985858
Keywords : anion recognition * host-guest systems * sulphonamides * electron-withdrawing groups * urea-based receptors
OECD category: Organic chemistry
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 N H 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 H 2 PO 4 ‐ and carboxylate anions, while those containing electron‐withdrawing groups inclined to deprotonation of sulphonamidic N H . 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/11104/0309765