Dataset for 2,4,5,7-Tetranitrofluorenone Oximate for the Naked-Eye Detection of H-Bond Donors and the Chiroptical Sensing of Enantiopure Reagents

Hydrogen bonding greatly influences rates and equilibrium positions of chemical reactions, conformations, and sometimes even stereochemistry. Herein, we report 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). Based on these results, 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.

Organizational unit

Laboratory of Professor Jérôme Lacour

Type

Dataset

DOI

10.26037/yareta:zadguods7jdvbfqee6keewwbuq

License

Creative Commons Attribution 4.0 International

Keywords

hydrogen bonds, solvatochromism, Asymmetric amplification, Circular dichroism, Pfeiffer effect