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Diaryl-Pyrano-Chromenes Atropisomers: Stereodynamics and Conformational Studies.
Ciogli, Alessia; Fochetti, Andrea; Sorato, Andrea; Fabrizi, Giancarlo; Matera, Nunzio; Mazzanti, Andrea; Mancinelli, Michele.
Afiliação
  • Ciogli A; Department of Chemistry and Drug Technologies, Sapienza University of Rome, Piazzale Aldo Moro 5, 00185 Roma, Italy.
  • Fochetti A; Department of Chemistry and Drug Technologies, Sapienza University of Rome, Piazzale Aldo Moro 5, 00185 Roma, Italy.
  • Sorato A; Department of Chemistry and Drug Technologies, Sapienza University of Rome, Piazzale Aldo Moro 5, 00185 Roma, Italy.
  • Fabrizi G; Department of Chemistry and Drug Technologies, Sapienza University of Rome, Piazzale Aldo Moro 5, 00185 Roma, Italy.
  • Matera N; Department of Industrial Chemistry "Toso Montanari", University of Bologna, Viale del Risorgimento 4, 40136 Bologna, Italy.
  • Mazzanti A; Department of Industrial Chemistry "Toso Montanari", University of Bologna, Viale del Risorgimento 4, 40136 Bologna, Italy.
  • Mancinelli M; Department of Industrial Chemistry "Toso Montanari", University of Bologna, Viale del Risorgimento 4, 40136 Bologna, Italy.
Molecules ; 28(13)2023 Jun 22.
Article em En | MEDLINE | ID: mdl-37446580
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.
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Texto completo: 1 Coleções: 01-internacional Base de dados: MEDLINE Assunto principal: Benzopiranos Idioma: En Ano de publicação: 2023 Tipo de documento: Article

Texto completo: 1 Coleções: 01-internacional Base de dados: MEDLINE Assunto principal: Benzopiranos Idioma: En Ano de publicação: 2023 Tipo de documento: Article