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

0570922 - ÚCHP 2024 RIV GB eng J - Journal Article
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
R&D Projects: GA ČR(CZ) GA20-07833S
Institutional support: RVO:67985858
Keywords : urea * conformational study * chiral recognition
OECD category: Organic chemistry
Impact factor: 3.3, year: 2022
Method of publishing: 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.
Permanent Link: https://hdl.handle.net/11104/0342263