π-Stacked polyphenolic dimers: A case study using dispersion-corrected methods

Imene Bayach; J.C. Sancho Garcia; Florent Di Meo; Jff Weber; Patrick Trouillas

π-Stacked polyphenolic dimers: A case study using dispersion-corrected methods

Imene Bayach ¹ J.C. Sancho Garcia ² Florent Di Meo ¹ Jff Weber ³ Patrick Trouillas ^{1, *}

* Auteur correspondant

1 LCSN - Laboratoire de Chimie des Substances Naturelles

2 Departamento Química Física, Universidad de Alicante, Ap. De Correos 99, E-03080 Alicante, Spain

3 Atta-ur-Rahman Institute for Natural Product Discovery (RiND), Universiti Teknologi MARA, Kampus Puncak Alam, 42300 Bandar Puncak Alam, Shah Alam Selangor DE, Malaysia

Abstract : The accuracy of dispersion-corrected calculations (DFT-D2, DFT-D3 and DFT-NL) is assessed here, with large basis sets (def2-QZVP) to avoid incompleteness effects, for the most stable structure of a real-world polyphenol dimer chosen as an appropriate model. Natural polyphenols form such complexes with π-stacking playing a key stabilizing role. Our benchmark calculations predict its existence favored by 22-24 kcal/mol with respect to the isolated monomers, mainly driven by both π-π and H-bonding interactions. The adequate comparison of lower-cost DFT-based methods allowed bracketing their expected accuracy. These results thus pave the way towards reliable studies of challenging aggregation processes of natural products.

Type de document :

Article dans une revue

Domaine :

Chimie / Chimie théorique et/ou physique

Liste complète des métadonnées

https://hal-unilim.archives-ouvertes.fr/hal-00937881
Contributeur : Vincent Sol <>
Soumis le : mardi 28 janvier 2014 - 21:33:26
Dernière modification le : mardi 20 mars 2018 - 16:36:18

π-Stacked polyphenolic dimers: A case study using dispersion-corrected methods

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π-Stacked polyphenolic dimers: A case study using dispersion-corrected methods

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