Tautomeric equilibrium in 1-benzamidoisoquinoline derivatives
dc.contributor.author
dc.date.accessioned
2023-09-08T09:45:42Z
dc.date.available
2023-09-08T09:45:42Z
dc.date.issued
2023-01-22
dc.identifier.issn
1420-3049
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dc.description.abstract
In this study, the tautomeric equilibrium of a sequence of 1-benzamidoisoquinoline derivatives was investigated with the tools of NMR spectroscopy and computational chemistry. The equilibrium between different tautomers in these systems could be controlled via the substitution effect, and the relative content of the amide form varied from 74% for the strong electron-donating NMe2 substituent to 38% for the strong electron-accepting NO2 group in the phenyl ring. In contrast to the previously investigated 2-phenacylquinoline derivatives, the most stable and thus most abundant tautomer in the 1-benzamidoisoquinoline series except the two most electron-accepting substituents was an amide. The intramolecular hydrogen bond present in the enol tautomer competed with the intermolecular hydrogen bonds created with the solvent molecules and thus was not a sufficient factor to favor this tautomer in the mixture. Although routinely computational studies of tautomeric equilibrium are performed within the continuum solvent models, it is proven here that the inclusion of the explicit solvent is mandatory in order to reproduce the experimental tendencies observed for this type of system, facilitating strong intermolecular hydrogen bonds
dc.format.mimetype
application/pdf
dc.language.iso
eng
dc.publisher
MDPI (Multidisciplinary Digital Publishing Institute)
dc.relation.isformatof
Reproducció digital del document publicat a: https://doi.org/10.3390/molecules28031101
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Molecules, 2023, vol. 28, núm. 3, p. 1101
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Articles publicats (D-Q)
dc.rights
Attribution 4.0 International (CC BY 4.0)
dc.rights.uri
dc.source
Rybczyński, Patryk Kaczmarek-Kędziera, Anna Iglesias Reguant, Alejandro Plazuk, Damian Ośmiałowski, Borys 2023 Tautomeric equilibrium in 1-benzamidoisoquinoline derivatives Molecules 28 3 1101
dc.subject
dc.title
Tautomeric equilibrium in 1-benzamidoisoquinoline derivatives
dc.type
info:eu-repo/semantics/article
dc.rights.accessRights
info:eu-repo/semantics/openAccess
dc.type.version
info:eu-repo/semantics/publishedVersion
dc.identifier.doi
dc.identifier.idgrec
036503
dc.type.peerreviewed
peer-reviewed
dc.identifier.eissn
1420-3049