Cargando…
A Study about Regioisomeric Hydroquinones with Multiple Intramolecular Hydrogen Bonding
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 o...
Autores principales: | , , , , |
---|---|
Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
MDPI
2017
|
Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6153943/ https://www.ncbi.nlm.nih.gov/pubmed/28387716 http://dx.doi.org/10.3390/molecules22040593 |
_version_ | 1783357598306664448 |
---|---|
author | Martínez-Cifuentes, Maximiliano Cardona, Wilson Saitz, Claudio Weiss-López, Boris Araya-Maturana, Ramiro |
author_facet | Martínez-Cifuentes, Maximiliano Cardona, Wilson Saitz, Claudio Weiss-López, Boris Araya-Maturana, Ramiro |
author_sort | Martínez-Cifuentes, Maximiliano |
collection | PubMed |
description | 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. |
format | Online Article Text |
id | pubmed-6153943 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2017 |
publisher | MDPI |
record_format | MEDLINE/PubMed |
spelling | pubmed-61539432018-11-13 A Study about Regioisomeric Hydroquinones with Multiple Intramolecular Hydrogen Bonding Martínez-Cifuentes, Maximiliano Cardona, Wilson Saitz, Claudio Weiss-López, Boris Araya-Maturana, Ramiro Molecules Article 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. MDPI 2017-04-07 /pmc/articles/PMC6153943/ /pubmed/28387716 http://dx.doi.org/10.3390/molecules22040593 Text en © 2017 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/). |
spellingShingle | Article Martínez-Cifuentes, Maximiliano Cardona, Wilson Saitz, Claudio Weiss-López, Boris Araya-Maturana, Ramiro A Study about Regioisomeric Hydroquinones with Multiple Intramolecular Hydrogen Bonding |
title | A Study about Regioisomeric Hydroquinones with Multiple Intramolecular Hydrogen Bonding |
title_full | A Study about Regioisomeric Hydroquinones with Multiple Intramolecular Hydrogen Bonding |
title_fullStr | A Study about Regioisomeric Hydroquinones with Multiple Intramolecular Hydrogen Bonding |
title_full_unstemmed | A Study about Regioisomeric Hydroquinones with Multiple Intramolecular Hydrogen Bonding |
title_short | A Study about Regioisomeric Hydroquinones with Multiple Intramolecular Hydrogen Bonding |
title_sort | study about regioisomeric hydroquinones with multiple intramolecular hydrogen bonding |
topic | Article |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6153943/ https://www.ncbi.nlm.nih.gov/pubmed/28387716 http://dx.doi.org/10.3390/molecules22040593 |
work_keys_str_mv | AT martinezcifuentesmaximiliano astudyaboutregioisomerichydroquinoneswithmultipleintramolecularhydrogenbonding AT cardonawilson astudyaboutregioisomerichydroquinoneswithmultipleintramolecularhydrogenbonding AT saitzclaudio astudyaboutregioisomerichydroquinoneswithmultipleintramolecularhydrogenbonding AT weisslopezboris astudyaboutregioisomerichydroquinoneswithmultipleintramolecularhydrogenbonding AT arayamaturanaramiro astudyaboutregioisomerichydroquinoneswithmultipleintramolecularhydrogenbonding AT martinezcifuentesmaximiliano studyaboutregioisomerichydroquinoneswithmultipleintramolecularhydrogenbonding AT cardonawilson studyaboutregioisomerichydroquinoneswithmultipleintramolecularhydrogenbonding AT saitzclaudio studyaboutregioisomerichydroquinoneswithmultipleintramolecularhydrogenbonding AT weisslopezboris studyaboutregioisomerichydroquinoneswithmultipleintramolecularhydrogenbonding AT arayamaturanaramiro studyaboutregioisomerichydroquinoneswithmultipleintramolecularhydrogenbonding |