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Interplay of π-stacking and inter-stacking interactions in two-component crystals of neutral closed-shell aromatic compounds: periodic DFT study

This paper bridges the gap between high-level ab initio computations of gas-phase models of 1 : 1 arene–arene complexes and calculations of the two-component (binary) organic crystals using atom–atom potentials. The studied crystals consist of electron-rich and electron-deficient compounds, which fo...

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Autores principales: Melikova, Sona M., Voronin, Alexander P., Panek, Jaroslaw, Frolov, Nikita E., Shishkina, Anastasia V., Rykounov, Alexey A., Tretyakov, Peter Yu., Vener, Mikhail V.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2020
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9055576/
https://www.ncbi.nlm.nih.gov/pubmed/35519116
http://dx.doi.org/10.1039/d0ra04799f
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author Melikova, Sona M.
Voronin, Alexander P.
Panek, Jaroslaw
Frolov, Nikita E.
Shishkina, Anastasia V.
Rykounov, Alexey A.
Tretyakov, Peter Yu.
Vener, Mikhail V.
author_facet Melikova, Sona M.
Voronin, Alexander P.
Panek, Jaroslaw
Frolov, Nikita E.
Shishkina, Anastasia V.
Rykounov, Alexey A.
Tretyakov, Peter Yu.
Vener, Mikhail V.
author_sort Melikova, Sona M.
collection PubMed
description This paper bridges the gap between high-level ab initio computations of gas-phase models of 1 : 1 arene–arene complexes and calculations of the two-component (binary) organic crystals using atom–atom potentials. The studied crystals consist of electron-rich and electron-deficient compounds, which form infinite stacks (columns) of heterodimers. The sublimation enthalpy of crystals has been evaluated by DFT periodic calculations, while intermolecular interactions have been characterized by Bader analysis of the periodic electronic density. The consideration of aromatic compounds without a dipole moment makes it possible to reveal the contribution of quadrupole–quadrupole interactions to the π-stacking energy. These interactions are significant for heterodimers formed by arenes with more than 2 rings, with absolute values of the traceless quadrupole moment (Q(zz)) larger than 10 D Å. The further aggregation of neighboring stacks is due to the C–H⋯F interactions in arene/perfluoroarene crystals. In crystals consisting of arene and an electron-deficient compound such as pyromellitic dianhydride, aggregation occurs due to the C–H⋯O interactions. The C–H⋯F and C–H⋯O inter-stacking interactions make the main contribution to the sublimation enthalpy, which exceeds 150 kJ mol(−1) for the two-component crystals formed by arenes with more than 2 rings.
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spelling pubmed-90555762022-05-04 Interplay of π-stacking and inter-stacking interactions in two-component crystals of neutral closed-shell aromatic compounds: periodic DFT study Melikova, Sona M. Voronin, Alexander P. Panek, Jaroslaw Frolov, Nikita E. Shishkina, Anastasia V. Rykounov, Alexey A. Tretyakov, Peter Yu. Vener, Mikhail V. RSC Adv Chemistry This paper bridges the gap between high-level ab initio computations of gas-phase models of 1 : 1 arene–arene complexes and calculations of the two-component (binary) organic crystals using atom–atom potentials. The studied crystals consist of electron-rich and electron-deficient compounds, which form infinite stacks (columns) of heterodimers. The sublimation enthalpy of crystals has been evaluated by DFT periodic calculations, while intermolecular interactions have been characterized by Bader analysis of the periodic electronic density. The consideration of aromatic compounds without a dipole moment makes it possible to reveal the contribution of quadrupole–quadrupole interactions to the π-stacking energy. These interactions are significant for heterodimers formed by arenes with more than 2 rings, with absolute values of the traceless quadrupole moment (Q(zz)) larger than 10 D Å. The further aggregation of neighboring stacks is due to the C–H⋯F interactions in arene/perfluoroarene crystals. In crystals consisting of arene and an electron-deficient compound such as pyromellitic dianhydride, aggregation occurs due to the C–H⋯O interactions. The C–H⋯F and C–H⋯O inter-stacking interactions make the main contribution to the sublimation enthalpy, which exceeds 150 kJ mol(−1) for the two-component crystals formed by arenes with more than 2 rings. The Royal Society of Chemistry 2020-07-27 /pmc/articles/PMC9055576/ /pubmed/35519116 http://dx.doi.org/10.1039/d0ra04799f Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by-nc/3.0/
spellingShingle Chemistry
Melikova, Sona M.
Voronin, Alexander P.
Panek, Jaroslaw
Frolov, Nikita E.
Shishkina, Anastasia V.
Rykounov, Alexey A.
Tretyakov, Peter Yu.
Vener, Mikhail V.
Interplay of π-stacking and inter-stacking interactions in two-component crystals of neutral closed-shell aromatic compounds: periodic DFT study
title Interplay of π-stacking and inter-stacking interactions in two-component crystals of neutral closed-shell aromatic compounds: periodic DFT study
title_full Interplay of π-stacking and inter-stacking interactions in two-component crystals of neutral closed-shell aromatic compounds: periodic DFT study
title_fullStr Interplay of π-stacking and inter-stacking interactions in two-component crystals of neutral closed-shell aromatic compounds: periodic DFT study
title_full_unstemmed Interplay of π-stacking and inter-stacking interactions in two-component crystals of neutral closed-shell aromatic compounds: periodic DFT study
title_short Interplay of π-stacking and inter-stacking interactions in two-component crystals of neutral closed-shell aromatic compounds: periodic DFT study
title_sort interplay of π-stacking and inter-stacking interactions in two-component crystals of neutral closed-shell aromatic compounds: periodic dft study
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9055576/
https://www.ncbi.nlm.nih.gov/pubmed/35519116
http://dx.doi.org/10.1039/d0ra04799f
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