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Molecules 2017, 22(8), 1294; doi:10.3390/molecules22081294

Intramolecular Hydrogen Bonding and Conformational Preferences of Arzanol—An Antioxidant Acylphloroglucinol

Department of Chemistry, University of Venda, Thohoyandou 0950, South Africa
Received: 7 June 2017 / Revised: 24 July 2017 / Accepted: 25 July 2017 / Published: 3 August 2017
(This article belongs to the Special Issue Intramolecular Hydrogen Bonding 2017)
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Abstract

Arzanol is a naturally-occurring prenylated acylphloroglucinol isolated from Helichrysum italicum and exhibiting anti-oxidant, antibiotic and antiviral activities. The molecule contains an α-pyrone moiety attached to the phloroglucinol moiety through a methylene bridge. The presence of several hydrogen bond donor or acceptor sites makes intramolecular hydrogen bonding patterns the dominant stabilising factor. Conformers with all the possible different hydrogen bonding patterns were calculated at the HF/6-31G(d,p) and DFT/B3LYP/6-31+G(d,p) levels with fully relaxed geometry in vacuo and in three solvents—chloroform, acetonitrile and water (these levels being chosen to enable comparisons with previous studies on acylphloroglucinols). Calculations in solution were performed with the Polarisable Continuum Model. The results show that the lowest energy conformers have the highest number of stronger intramolecular hydrogen bonds. The influence of intramolecular hydrogen bonding patterns on the other molecular properties is also analysed. View Full-Text
Keywords: acylphloroglucinols; antioxidants; arzanol; intramolecular hydrogen bonding; polyphenolic compounds; O–H···π interaction acylphloroglucinols; antioxidants; arzanol; intramolecular hydrogen bonding; polyphenolic compounds; O–H···π interaction
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Mammino, L. Intramolecular Hydrogen Bonding and Conformational Preferences of Arzanol—An Antioxidant Acylphloroglucinol. Molecules 2017, 22, 1294.

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