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

  • Liliana MamminoEmail author
Regular Article
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Part of the following topical collections:
  1. CHITEL 2017 - Paris - France

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.

Keywords

Acylphloroglucinols Antioxidants Complexes of organic molecules with metal ions Geranylated acylphloroglucinols Intramolecular hydrogen bonding Molecule–ion interaction 

Supplementary material

214_2018_2381_MOESM1_ESM.pdf (14.6 mb)
Supplementary material 1 (PDF 14910 kb)
214_2018_2381_MOESM2_ESM.pdf (1.7 mb)
Supplementary material 2 (PDF 1726 kb)

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Copyright information

© Springer-Verlag GmbH Germany, part of Springer Nature 2019

Authors and Affiliations

  1. 1.Department of ChemistryUniversity of VendaThohoyandouSouth Africa

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