A study about regioisomeric hydroquinones with multiple intramolecular hydrogen bonding

Maximiliano Martínez-Cifuentes, Wilson Cardona, Claudio Saitz, Boris Weiss-López, Ramiro Araya-Maturana

Resultado de la investigación: Contribución a una revistaArtículo

7 Citas (Scopus)

Resumen

A 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.

Idioma originalInglés
Número de artículo593
PublicaciónMolecules
Volumen22
N.º4
DOI
EstadoPublicada - 1 abr 2017

Áreas temáticas de ASJC Scopus

  • Medicina (todo)
  • Química orgánica

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    Martínez-Cifuentes, M., Cardona, W., Saitz, C., Weiss-López, B., & Araya-Maturana, R. (2017). A study about regioisomeric hydroquinones with multiple intramolecular hydrogen bonding. Molecules, 22(4), [593]. https://doi.org/10.3390/molecules22040593