NDLI: A Study about Regioisomeric Hydroquinones with Multiple Intramolecular Hydrogen Bonding

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A Study about Regioisomeric Hydroquinones with Multiple Intramolecular Hydrogen Bonding

Content Provider	MDPI
Author	Martínez-Cifuentes, Maximiliano Cardona, Wilson Saitz, Claudio Weiss-López, Boris Araya-Maturana, Ramiro
Abstract	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.
File Size	7653376
File Format	PDF
e-ISSN	14203049
DOI	10.3390/molecules22040593
Journal	Molecules
Issue Number	4
Volume Number	22
Language	English
Publisher Date	2017-04-07
Access Restriction	Open
Subject Keyword	hydroquinone hydrogen bond DFT NBO AIM
Content Type	Text
Resource Type	Article

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