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Complexes of 1-[3-geranyl-2,4,6-trihydroxyphenyl]-2-methylpropan-1-one with a Cu2+ ion: a DFT study

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Abstract

1-[3-geranyl-2,4,6-trihydroxyphenyl]-2-methylpropan-1-one (GTM) is an acylphloroglucinol present in various plants. Its structure is largely close to that of hyperjovinol A (HPJA)—a compound with proven good antioxidant activity. Complexes of the GTM molecule with a Cu2+ ion were calculated considering all the sites to which the Cu2+ ion may bind (the four O atoms in the acylphloroglucinol moiety and the two C=C π bonds in the geranyl chain) and including also simultaneous coordination to two or three sites, when geometrically possible. Calculations were performed at the DFT level with the B3LYP functional, the 6-31+G(d,p) basis set for the C, O and H atoms and the LANL2DZ pseudopotential for the Cu2+ ion. The results show that Cu2+ is effectively reduced to Cu+ in all the calculated complexes. Comparisons with analogous complexes of related molecular structures are utilised to evaluate the influence of specific structural features on the molecule’s complexation and reducing ability. Comparisons with the complexes of a structure in which the first π bond in the geranyl chain is removed (GTM-P2) enable an evaluation of the relevance of this π bond. Comparisons with the complexes of a structure in which the geranyl chain is replaced by a prenyl chain (GTM-PR) enable an evaluation of the relevance of the second π bond in the geranyl chain. Comparisons with the complexes of HPJA enable an evaluation of the relative effects of an OH group or a π bond on the molecule’s reducing ability. The energy lowering on complexation is greatest for HPJA, nearly comparable for GTM and GTM-P2 and smallest for GTM-PR.

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  1. Department of Chemistry, University of Venda, Thohoyandou, South Africa

    Liliana Mammino

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  1. Liliana Mammino
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Correspondence to Liliana Mammino.

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Published as part of the special collection of articles “CHITEL 2017 - Paris - France”.

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Mammino, L. Complexes of 1-[3-geranyl-2,4,6-trihydroxyphenyl]-2-methylpropan-1-one with a Cu2+ ion: a DFT study. Theor Chem Acc 138, 15 (2019). https://doi.org/10.1007/s00214-018-2381-2

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