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- Title
2,4,5,7‐Tetranitrofluorenone Oximate for the Naked‐Eye Detection of H‐Bond Donors and the Chiroptical Sensing of Enantiopure Reagents.
- Authors
Pál, Dávid; Besnard, Céline; de Aguirre, Adiran; Poblador‐Bahamonde, Amalia I.; Pescitelli, Gennaro; Lacour, Jérôme
- Abstract
Hydrogen bonding greatly influences rates and equilibrium positions of chemical reactions, conformations, and sometimes even stereochemistry. This study reports on tetranitrofluorenone oximate, a novel dye capable of naked‐eye detection of hydrogen‐bond donating species (HBDs) and of rapid determination of H‐bond donation strength by hypsochromic shift monitoring. In addition, the molecule possesses atropisomeric conformations, of M and P configuration, as evidenced in solid and solution state studies by X‐ray diffraction and electronic circular dichroism (ECD), respectively. In the latter case, enantiopure bis‐thioureas were the most effective HBDs to promote a chiral induction (diastereoselective recognition, Pfeiffer effect); the ECD results being rationalized by time‐dependent density functional theory (TDDFT) calculations. Based on these experiments, bis‐thioureas were used as chiral reagents in asymmetric 1,3‐dipolar cycloadditions of structurally‐related nitrones; the ECD sensing of the stereoinduction between bis‐thioureas and the oximate serving as an indirect method of selection of the most effective HBD for asymmetric synthesis.
- Subjects
ISOXAZOLIDINES; RING formation (Chemistry); CHEMICAL equilibrium; TIME-dependent density functional theory; CHEMICAL reactions; ASYMMETRIC synthesis; STEREOCHEMISTRY
- Publication
Chemistry - A European Journal, 2023, Vol 29, Issue 60, p1
- ISSN
0947-6539
- Publication type
Article
- DOI
10.1002/chem.202302169