Tautomerism and conformational analysis in 3-fluoropiperidin-2-one inform on F···HO intramolecular hydrogen bond

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MetadadosDescriçãoIdioma
Autor(es): dc.creatorSilla, Josué M.-
Autor(es): dc.creatorFreitas, Matheus P.-
Data de aceite: dc.date.accessioned2026-02-09T11:15:46Z-
Data de disponibilização: dc.date.available2026-02-09T11:15:46Z-
Data de envio: dc.date.issued2020-05-12-
Data de envio: dc.date.issued2020-05-12-
Data de envio: dc.date.issued2019-01-
Fonte completa do material: dc.identifierhttps://repositorio.ufla.br/handle/1/40848-
Fonte completa do material: dc.identifierhttps://www.sciencedirect.com/science/article/abs/pii/S002211391830383X#!-
Fonte: dc.identifier.urihttp://educapes.capes.gov.br/handle/capes/1137107-
Descrição: dc.descriptionWhether hydroxyl hydrogen is directed towards a Lewis base substituent in an alkyl chain due to intramolecular hydrogen bonds or to avoid repulsion between the hydroxyl oxygen and the substituent is a debatable topic and difficult to probe. This is still more challenging when fluorine is the Lewis base substituent. This work reports a theoretical approach capable of dissecting the contributions from hydrogen bond and repulsion, allowing to decide which interaction dominates the orientation of the hydroxyl group in a high-energy tautomer of 3-fluoropiperidin-2-one. A comparison between the potential energy curves for the hydroxyl rotation in the axial and equatorial conformers revealed that repulsion between fluorine and oxygen contributes by ca. 1.2 kcal mol−1 to destabilize the cis isomer, while intramolecular hydrogen bond between fluorine and the hydroxyl group amounts by ca. 0.9 kcal mol−1 favoring the trans isomer. These are not the major effects governing the conformational equilibrium of the studied compound, which is rather dictated by N⋯O steric repulsion, but the obtained outcomes can be valuable to understand the role of F⋯H(O) hydrogen bonds in conformational analysis and, ultimately, in the design of performance fluorinated aliphatic alcohols.-
Idioma: dc.languageen-
Publicador: dc.publisherElsevier-
Direitos: dc.rightsrestrictAccess-
???dc.source???: dc.sourceJournal of Fluorine Chemistry-
Palavras-chave: dc.subjectOrganofluorines-
Palavras-chave: dc.subjectConformational analysis-
Palavras-chave: dc.subjectHydrogen bond-
Palavras-chave: dc.subjectSteric repulsions-
Palavras-chave: dc.subjectTheoretical calculations-
Palavras-chave: dc.subjectOrganofluorinos-
Palavras-chave: dc.subjectAnálise conformacional-
Palavras-chave: dc.subjectLigações de hidrogênio-
Palavras-chave: dc.subjectRepulsões estéricas-
Título: dc.titleTautomerism and conformational analysis in 3-fluoropiperidin-2-one inform on F···HO intramolecular hydrogen bond-
Tipo de arquivo: dc.typeArtigo-
Aparece nas coleções:Repositório Institucional da Universidade Federal de Lavras (RIUFLA)

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