Binaphthalene-based cyclic homochiral ureas and their structure-related properties

0570922 - ÚCHP 2024 RIV GB eng J - Článek v odborném periodiku
Holakovský, R. - Just, D. - Eigner, V. - Jakubec, Martin - Cuřínová, Petra
Binaphthalene-based cyclic homochiral ureas and their structure-related properties.
New Journal of Chemistry. Roč. 47, č. 18 (2023), s. 8515-8523. ISSN 1144-0546. E-ISSN 1369-9261
Grant CEP: GA ČR(CZ) GA20-07833S
Institucionální podpora: RVO:67985858
Klíčová slova: urea * conformational study * chiral recognition
Obor OECD: Organic chemistry
Impakt faktor: 3.3, rok: 2022
Způsob publikování: Open access
https://pubs.rsc.org/en/content/articlepdf/2023/nj/d2nj06147c

Enantiomeric purity control is a must when working with chiral drugs. In this context, homochiral cycles consisting solely of 1 to 3 binaphthalene units interconnected with urea moieties were tested as chiral solvating agents for enantiomers of naproxen. Among the tested compounds, only the dimeric structure formed stable diastereomeric complexes with naproxen with KR = 43±3 M-1/ Ks = 34±2 M-1. When the conformational mobility of the dimer was decelerated by cooling to -30 °C, the complexes became stronger (KR-30 = 100±6 M-1/ KS-30 = 102±7 M-1). Using DFT calculation, probable structures of the diastereomeric complex were proposed.
Trvalý link: https://hdl.handle.net/11104/0342263