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dc.contributor.author
Vallejos, Margarita
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dc.contributor.author
Labadie, Guillermo Roberto
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dc.date.available
2020-09-03T15:56:21Z
dc.date.issued
2020-01
dc.identifier.citation
Vallejos, Margarita; Labadie, Guillermo Roberto; Insight into the factors controlling the equilibrium of allylic azides; Royal Society of Chemistry; RSC Advances; 10; 8; 1-2020; 4404-4413
dc.identifier.issn
2046-2069
dc.identifier.uri
http://hdl.handle.net/11336/113124
dc.description.abstract
Several allylic azides with different double bond substitutions were studied to understand the factors, governing their equilibrium using density functional theory along with the quantum theory of atoms in molecules, non-covalent interactions and natural bond orbital approaches. The results showed that the hydroxyl group or heteroatoms in allylic azides interact with the molecule through an electrostatic weak interaction in each pair of regioisomers. The equilibrium shifts of substituted allylic azides, compared to non-substituted allylic azides, were not attributed to the presence of specific interactions, such as hydrogen bonds. The observed equilibrium shifts stemmed mainly from the strengthening and weakening of negative hyperconjugative interactions, which were affected by the weak interaction involving the proximal substituent in each regioisomer. A good linear correlation was obtained between the hyperconjugative energies of πC[double bond, length as m-dash]C→σ*Zb interactions and the calculated percentages of the secondary azide and tertiary azide in the equilibrium mixture. Also, the effect of the aromatic ring substituent was analysed using such approaches. This study not only provides insights into the factors controlling the stabilities of the substituted allylic azides, but also settles the basis to predict the regioisomer predominance in the equilibrium mixture.
dc.format
application/pdf
dc.language.iso
eng
dc.publisher
Royal Society of Chemistry
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dc.rights
info:eu-repo/semantics/openAccess
dc.rights.uri
https://creativecommons.org/licenses/by/2.5/ar/
dc.subject
WINSTEIN'S REARRANGEMENT
dc.subject
QTAIM
dc.subject
NBO
dc.subject
NCI
dc.subject
DFT
dc.subject.classification
Química Orgánica
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dc.subject.classification
Ciencias Químicas
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dc.subject.classification
CIENCIAS NATURALES Y EXACTAS
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dc.title
Insight into the factors controlling the equilibrium of allylic azides
dc.type
info:eu-repo/semantics/article
dc.type
info:ar-repo/semantics/artículo
dc.type
info:eu-repo/semantics/publishedVersion
dc.date.updated
2020-06-23T14:43:11Z
dc.journal.volume
10
dc.journal.number
8
dc.journal.pagination
4404-4413
dc.journal.pais
Reino Unido
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dc.description.fil
Fil: Vallejos, Margarita. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Nordeste. Instituto de Química Básica y Aplicada del Nordeste Argentino. Universidad Nacional del Nordeste. Facultad de Ciencias Exactas Naturales y Agrimensura. Instituto de Química Básica y Aplicada del Nordeste Argentino; Argentina
dc.description.fil
Fil: Labadie, Guillermo Roberto. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; Argentina. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas; Argentina
dc.journal.title
RSC Advances
dc.relation.alternativeid
info:eu-repo/semantics/altIdentifier/url/http://xlink.rsc.org/?DOI=C9RA10093H
dc.relation.alternativeid
info:eu-repo/semantics/altIdentifier/doi/http://dx.doi.org/10.1039/C9RA10093H
dc.relation.alternativeid
info:eu-repo/semantics/altIdentifier/url/https://pubs.rsc.org/en/content/articlelanding/2020/ra/c9ra10093h#!divAbstract
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