The dynamic scenario of di-aryls-pyrano-chromenes was investigated using DFT calculations. The symmetry of the chromene scaffold and the presence of two ortho-substituted aryls substituents can generate two syn/anti diastereoisomers and conformational enantiomers with different rotational barriers. The relative conformations and configurations were derived using NOESY-1D experiments. Depending on the energies related to the conformational exchange, the experimental energy barriers were determined through Dynamic NMR, Dynamic HPLC or kinetic studies. The atropisomeric pairs were resolved in the latter scenario, and their absolute configuration was assigned using the ECD/TD-DFT method.

Diaryl-Pyrano-Chromenes Atropisomers: Stereodynamics and Conformational Studies / Ciogli A.; Fochetti A.; Sorato A.; Fabrizi G.; Matera N.; Mazzanti A.; Mancinelli M.. - In: MOLECULES. - ISSN 1420-3049. - ELETTRONICO. - 28:13(2023), pp. 4915.1-4915.17. [10.3390/molecules28134915]

Diaryl-Pyrano-Chromenes Atropisomers: Stereodynamics and Conformational Studies

Matera N.;Mazzanti A.;Mancinelli M.
2023

Abstract

The dynamic scenario of di-aryls-pyrano-chromenes was investigated using DFT calculations. The symmetry of the chromene scaffold and the presence of two ortho-substituted aryls substituents can generate two syn/anti diastereoisomers and conformational enantiomers with different rotational barriers. The relative conformations and configurations were derived using NOESY-1D experiments. Depending on the energies related to the conformational exchange, the experimental energy barriers were determined through Dynamic NMR, Dynamic HPLC or kinetic studies. The atropisomeric pairs were resolved in the latter scenario, and their absolute configuration was assigned using the ECD/TD-DFT method.
2023
Diaryl-Pyrano-Chromenes Atropisomers: Stereodynamics and Conformational Studies / Ciogli A.; Fochetti A.; Sorato A.; Fabrizi G.; Matera N.; Mazzanti A.; Mancinelli M.. - In: MOLECULES. - ISSN 1420-3049. - ELETTRONICO. - 28:13(2023), pp. 4915.1-4915.17. [10.3390/molecules28134915]
Ciogli A.; Fochetti A.; Sorato A.; Fabrizi G.; Matera N.; Mazzanti A.; Mancinelli M.
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11585/956015
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