Stacking Interactions of Resonance-Assisted Hydrogen-Bridged Rings and C6-Aromatic Rings
Abstract
Stacking interactions between six-membered resonance-assisted hydrogen-bridged rings (RAHB) and C6-aromatic rings are systematically studied by analyzing crystal structures in Cambridge Structural Database (CSD). The interaction energies were calculated by quantum-chemical methods. Although the interactions are stronger than benzene/benzene stacking interactions (-2.7 kcal/mol) the strongest calculated RAHB/benzene stacking interaction (-3.7 kcal/mol) is significantly weaker than the strongest calculated RAHB/RAHB stacking interaction (-4.7 kcal/mol), but for particular composition of RAHB rings RAHB/benzene stacking interactions can be weaker or stronger than the corresponding RAHB/RAHB stacking interactions. They are also weaker than the strongest calculated stacking interaction between five-membered saturated hydrogen-bridged rings and benzene (-4.4 kcal/mol) and between two five-membered saturated hydrogen-bridged rings (-4.9 kcal/mol). SAPT energy decomposition analyses show that ...the strongest attractive term in RAHB/benzene stacking interactions is dispersion, however, it is mostly canceled by repulsive exchange term, hence the geometries of the most stable structures are determined by electrostatic term.
Source:
Physical Chemistry Chemical Physics, 2020, 22, 24, 13721-13728Publisher:
- Royal Society of Chemistry
Funding / projects:
- Noncovalent interactions of pi-systems and their role in molecular recognition (RS-172065)
- Qatar National Research Fund (NPRP8-425-1-087)
Note:
- This is the peer-reviewed version of the following article: Filipović, J. P. B.; Hall, M. B.; Zarić, S. D. Stacking Interactions of Resonance-Assisted Hydrogen-Bridged Rings and C6-Aromatic Rings. Physical Chemistry Chemical Physics 2020, 22 (24), 13721–13728. https://doi.org/10.1039/d0cp01624A.
- Supplementary material: https://cherry.chem.bg.ac.rs/handle/123456789/4079
- Related to published version: https://cherry.chem.bg.ac.rs/handle/123456789/4060
Related info:
- Version of
https://doi.org/10.1039/D0CP01624A - Referenced by
https://cherry.chem.bg.ac.rs/handle/123456789/4079
DOI: 10.1039/D0CP01624A
ISSN: 1463-9076
WoS: 000542478100037
Scopus: 2-s2.0-85087096113
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Institution/Community
Inovacioni centar / Innovation CentreTY - JOUR AU - Blagojević Filipović, Jelena P. AU - Hall, Michael B. AU - Zarić, Snežana D. PY - 2020 UR - http://cherry.chem.bg.ac.rs/handle/123456789/5307 AB - Stacking interactions between six-membered resonance-assisted hydrogen-bridged rings (RAHB) and C6-aromatic rings are systematically studied by analyzing crystal structures in Cambridge Structural Database (CSD). The interaction energies were calculated by quantum-chemical methods. Although the interactions are stronger than benzene/benzene stacking interactions (-2.7 kcal/mol) the strongest calculated RAHB/benzene stacking interaction (-3.7 kcal/mol) is significantly weaker than the strongest calculated RAHB/RAHB stacking interaction (-4.7 kcal/mol), but for particular composition of RAHB rings RAHB/benzene stacking interactions can be weaker or stronger than the corresponding RAHB/RAHB stacking interactions. They are also weaker than the strongest calculated stacking interaction between five-membered saturated hydrogen-bridged rings and benzene (-4.4 kcal/mol) and between two five-membered saturated hydrogen-bridged rings (-4.9 kcal/mol). SAPT energy decomposition analyses show that the strongest attractive term in RAHB/benzene stacking interactions is dispersion, however, it is mostly canceled by repulsive exchange term, hence the geometries of the most stable structures are determined by electrostatic term. PB - Royal Society of Chemistry T2 - Physical Chemistry Chemical Physics T1 - Stacking Interactions of Resonance-Assisted Hydrogen-Bridged Rings and C6-Aromatic Rings VL - 22 IS - 24 SP - 13721 EP - 13728 DO - 10.1039/D0CP01624A ER -
@article{ author = "Blagojević Filipović, Jelena P. and Hall, Michael B. and Zarić, Snežana D.", year = "2020", abstract = "Stacking interactions between six-membered resonance-assisted hydrogen-bridged rings (RAHB) and C6-aromatic rings are systematically studied by analyzing crystal structures in Cambridge Structural Database (CSD). The interaction energies were calculated by quantum-chemical methods. Although the interactions are stronger than benzene/benzene stacking interactions (-2.7 kcal/mol) the strongest calculated RAHB/benzene stacking interaction (-3.7 kcal/mol) is significantly weaker than the strongest calculated RAHB/RAHB stacking interaction (-4.7 kcal/mol), but for particular composition of RAHB rings RAHB/benzene stacking interactions can be weaker or stronger than the corresponding RAHB/RAHB stacking interactions. They are also weaker than the strongest calculated stacking interaction between five-membered saturated hydrogen-bridged rings and benzene (-4.4 kcal/mol) and between two five-membered saturated hydrogen-bridged rings (-4.9 kcal/mol). SAPT energy decomposition analyses show that the strongest attractive term in RAHB/benzene stacking interactions is dispersion, however, it is mostly canceled by repulsive exchange term, hence the geometries of the most stable structures are determined by electrostatic term.", publisher = "Royal Society of Chemistry", journal = "Physical Chemistry Chemical Physics", title = "Stacking Interactions of Resonance-Assisted Hydrogen-Bridged Rings and C6-Aromatic Rings", volume = "22", number = "24", pages = "13721-13728", doi = "10.1039/D0CP01624A" }
Blagojević Filipović, J. P., Hall, M. B.,& Zarić, S. D.. (2020). Stacking Interactions of Resonance-Assisted Hydrogen-Bridged Rings and C6-Aromatic Rings. in Physical Chemistry Chemical Physics Royal Society of Chemistry., 22(24), 13721-13728. https://doi.org/10.1039/D0CP01624A
Blagojević Filipović JP, Hall MB, Zarić SD. Stacking Interactions of Resonance-Assisted Hydrogen-Bridged Rings and C6-Aromatic Rings. in Physical Chemistry Chemical Physics. 2020;22(24):13721-13728. doi:10.1039/D0CP01624A .
Blagojević Filipović, Jelena P., Hall, Michael B., Zarić, Snežana D., "Stacking Interactions of Resonance-Assisted Hydrogen-Bridged Rings and C6-Aromatic Rings" in Physical Chemistry Chemical Physics, 22, no. 24 (2020):13721-13728, https://doi.org/10.1039/D0CP01624A . .