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Conformational preferences and intramolecular hydrogen bonding patterns of tetraflavaspidic acid BBBB – a tetrameric acylphloroglucinol

  • Liliana Mammino EMAIL logo
Published/Copyright: May 10, 2022
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Physical Sciences Reviews
From the journal Physical Sciences Reviews Volume 8 Issue 11

Abstract

Tetraflavaspidic acid BBBB is a tetrameric acylphloroglucinol of natural origin isolated from Dryopteris aitoniana. Its molecule consists of four acylphloroglucinol units linked by methylene bridges and having the same R = propyl in their R−C=O groups. In one of the terminal monomers, one of the OHs ortho to R−C=O is replaced by a keto O. The paper reports the results of a conformational study performed at the HF/6-31G(d,p) and DFT/B3LYP/6-31+G(d,p) levels; two options are utilised for the latter, without and with the inclusion of the Grimme’s dispersion correction. Given the importance of intramolecular hydrogen bonds (IHBs) for the stabilisation of acylphloroglucinol conformers, only conformers containing the maximum IHBs’ number were calculated. The IHBs comprise an IHB between the sp2 O of R−C=O and a neighbouring OH in each monomeric unit and two inter-monomer IHBs between each pair of units. The single C−C bonds of the methylene bridges enable a variety of mutual orientations of the monomeric units, giving rise to a variety of conformations and IHB patterns. The results indicate greater stability for conformers in which individual monomers take lower energy conformations, and significant influence of the dispersion correction on the estimation of the energetics and of other molecular properties. The inclusion of the dispersion correction also strongly limits the number of low energy conformers. The influence of dispersion effects is consistent with the presence of four aromatic rings.

Keywords: acylphloroglucinols; dispersion effects; Grimme’s dispersion correction; intramolecular hydrogen bonding; tetrameric acylphloroglucinols
Corresponding author: Liliana Mammino, School of Mathematical and Natural Sciences, University of Venda, Thohoyandou, South Africa, E-mail:

Acknowledgments

The author expresses her gratitude to the Centre for High Performance Computing (CHPC) in Cape Town (South Africa) for providing the facilities to perform the calculations needed for this work.

  1. Author contribution: The author has accepted responsibility for the entire content of this submitted manuscript and approved submission.

  2. Research funding: None declared.

  3. Conflict of interest statement: The author declares no conflicts of interest regarding this article.

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Supplementary Material

The online version of this article offers supplementary material (https://doi.org/10.1515/psr-2021-0239).

Published Online: 2022-05-10

© 2022 Walter de Gruyter GmbH, Berlin/Boston

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https://doi.org/10.1515/psr-2021-0239
Keywords for this article
acylphloroglucinols; dispersion effects; Grimme’s dispersion correction; intramolecular hydrogen bonding; tetrameric acylphloroglucinols

Articles in the same Issue

  1. Frontmatter
  2. Reviews
  3. Anticancer properties of arylchromenes and arylchromans: an overview
  4. Solid state lithium ion conductors for lithium batteries
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  6. Use of biochemical markers for diabetes prevention in the new decade
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  8. Alkaline-earth metal(II) complexes of salinomycin – spectral properties and antibacterial activity
  9. Use of heterogeneous catalysis in sustainable biofuel production
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