A study about regioisomeric hydroquinones with multiple intramolecular hydrogen bonding

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dc.contributor.authorMartínez-Cifuentes, M.
dc.contributor.authorCardona, W.
dc.contributor.authorSaitz, C.
dc.contributor.authorWeiss-López, B.
dc.contributor.authorAraya-Maturana, R.
dc.date.accessioned2017-11-24T14:30:36Z
dc.date.available2017-11-24T14:30:36Z
dc.date.issued2017-04
dc.descriptionIndexación: Web of Science; Scopus.es_CL
dc.description.abstractA theoretical exploration about hydrogen bonding in a series of synthetic regioisomeric antitumor tricyclic hydroquinones is presented. The stabilization energy for the intramolecular hydrogen bond (IHB) formation in four structurally different situations were evaluated: (a) IHB between the proton of a phenolic hydroxyl group and an ortho-carbonyl group (forming a six-membered ring); (b) between the oxygen atom of a phenolic hydroxyl group and the proton of an hydroxyalkyl group (seven membered ring); (c) between the proton of a phenolic hydroxyl group with the oxygen atom of the hydroxyl group of a hydroxyalkyl moiety (seven-membered ring); and (d) between the proton of a phenolic hydroxyl group and an oxygen atom directly bonded to the aromatic ring in ortho position (five-membered ring). A conformational analysis for the rotation around the hydroxyalkyl substituent is also performed. It is observed that there is a correspondence between the conformational energies and the IHB. The strongest intramolecular hydrogen bonds are those involving a phenolic proton and a carbonyl oxygen atom, forming a six-membered ring, and the weakest are those involving a phenolic proton with the oxygen atom of the chromenone, forming five-membered rings. Additionally, the synthesis and structural assignment of two pairs of regioisomeric hydroquinones, by 2D-NMR experiments, are reported. These results can be useful in the design of biologically-active molecules.es_CL
dc.description.urihttp://www.mdpi.com/1420-3049/22/4/593
dc.identifier.citationMolecules. Volume 22, Issue 4, April 2017, Article number 593es_CL
dc.identifier.issn1420-3049
dc.identifier.otherDOI: 10.3390/molecules22040593
dc.identifier.urihttp://repositorio.unab.cl/xmlui/handle/ria/4723
dc.language.isoenes_CL
dc.publisherMDPIes_CL
dc.subjectAIMes_CL
dc.subjectDFTes_CL
dc.subjectHydrogen bondes_CL
dc.subjectHydroquinonees_CL
dc.subjectNBOes_CL
dc.titleA study about regioisomeric hydroquinones with multiple intramolecular hydrogen bondinges_CL
dc.typeArtículoes_CL
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