On the Nature of the Rotational Energy Barrier of Atropisomeric Hydrazides

N-N atropisomers represent a useful class of compounds that has recently received important attention from many research groups. This article presents an in-depth analysis of the energy barrier needed for the racemization process of atropoisomeric hydrazides, combining an experimental and computatio...

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Bibliographic Details
Published in:Molecules (Basel, Switzerland) Switzerland), 2023-11, Vol.28 (23), p.7856
Main Authors: Pellegrini, Andrea, Marcon, Laura, Righi, Paolo, Centonze, Giovanni, Portolani, Chiara, Capodiferro, Marco, Oljira, Shilashi Badasa, Manetto, Simone, Ciogli, Alessia, Bencivenni, Giorgio
Format: Article
Language:English
Subjects:
Bonds
Chemical bonds
dynamic-HPLC
Energy
Geometry
hydrazides
N-N atropisomers
Nitrogen
Optimization
Organic compounds
racemization
Synthesis
Temperature
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Summary:N-N atropisomers represent a useful class of compounds that has recently received important attention from many research groups. This article presents an in-depth analysis of the energy barrier needed for the racemization process of atropoisomeric hydrazides, combining an experimental and computational approach. The focus is on examining how electronic and steric factors impact the racemization process. The results obtained indicate that the barrier observed during the racemization process mainly arises from an increase in the p-orbital character of the nitrogen atoms.
ISSN:1420-3049
1420-3049
DOI:10.3390/molecules28237856