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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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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container_issue 23
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container_title Molecules (Basel, Switzerland)
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creator Pellegrini, Andrea
Marcon, Laura
Righi, Paolo
Centonze, Giovanni
Portolani, Chiara
Capodiferro, Marco
Oljira, Shilashi Badasa
Manetto, Simone
Ciogli, Alessia
Bencivenni, Giorgio
description 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.
doi_str_mv 10.3390/molecules28237856
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subjects Bonds
Chemical bonds
dynamic-HPLC
Energy
Geometry
hydrazides
N-N atropisomers
Nitrogen
Optimization
Organic compounds
racemization
Synthesis
Temperature
title On the Nature of the Rotational Energy Barrier of Atropisomeric Hydrazides
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