Intramolecular interactions contributing for the conformational preference of bioactive diphenhydramine: manifestation of the gauche effect

Registro completo de metadados
MetadadosDescriçãoIdioma
Autor(es): dc.creatorRezende, Fátima M.P.de-
Autor(es): dc.creatorAndrade, Laize A.F.-
Autor(es): dc.creatorFreitas, Matheus P.-
Data de aceite: dc.date.accessioned2026-02-09T12:46:52Z-
Data de disponibilização: dc.date.available2026-02-09T12:46:52Z-
Data de envio: dc.date.issued2020-07-12-
Data de envio: dc.date.issued2020-07-12-
Data de envio: dc.date.issued2015-08-05-
Fonte completa do material: dc.identifierhttps://repositorio.ufla.br/handle/1/41857-
Fonte completa do material: dc.identifierhttps://www.sciencedirect.com/science/article/abs/pii/S0022286015002689-
Fonte: dc.identifier.urihttp://educapes.capes.gov.br/handle/capes/1168145-
Descrição: dc.descriptionDiphenhydramine is an antihistamine used to treat some symptoms of allergies and the common cold. It is usually marketed as the hydrochloride salt, and both the neutral and cation forms have the O–C–C–N fragment. The gauche effect is well known in fluorine-containing chains, because its main origin is hyperconjugative and the σ∗C–F is a low-lying acceptor orbital, allowing electron delocalization in the conformation where F and an adjacent electronegative substituent in an ethane fragment are in the gauche orientation. Our experimental (NMR) and theoretical findings indicate that diphenhydramine exhibits the gauche effect, since the preferential conformations have the O–C–C–N moiety in this orientation due especially to antiperiplanar σC–H → σ∗C–O and σC–H → σ∗C–N interactions. This conformational preference is strengthened in the protonated form due to an incremental electrostatic gauche effect. Because the gauche conformation matches the bioactive structure of diphenhydramine complexed with histamine methyltransferase, it is suggested that intramolecular interactions, and not only induced fit, rule its bioactive form.-
Idioma: dc.languageen-
Publicador: dc.publisherElsevier-
Direitos: dc.rightsrestrictAccess-
???dc.source???: dc.sourceJournal of Molecular Structure-
Palavras-chave: dc.subjectDiphenhydramine-
Palavras-chave: dc.subjectGauche effect-
Palavras-chave: dc.subjectHyperconjugation-
Palavras-chave: dc.subjectElectrostatic effects-
Palavras-chave: dc.subjectHydrogen bonding-
Título: dc.titleIntramolecular interactions contributing for the conformational preference of bioactive diphenhydramine: manifestation of the gauche effect-
Tipo de arquivo: dc.typeArtigo-
Aparece nas coleções:Repositório Institucional da Universidade Federal de Lavras (RIUFLA)

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