What Is Special about Aromatic-Aromatic Interactions? Significant Attraction at Large Horizontal Displacement
Authors
Ninković, DraganBlagojević Filipović, Jelena P.
Hall, Michael B.
Brothers, Edward N.
Zarić, Snežana D.
Article (Published version)
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High-level ab initio calculations show that the most stable stacking for benzene-cyclohexane is 17% stronger than that for benzene-benzene. However, as these systems are displaced horizontally the benzene-benzene attraction retains its strength. At a displacement of 5.0 Å, the benzene-benzene attraction is still ∼70% of its maximum strength, while benzene-cyclohexane attraction has fallen to ∼40% of its maximum strength. Alternatively, the radius of attraction (>2.0 kcal/mol) for benzene-benzene is 250% larger than that for benzene-cyclohexane. Thus, at relatively large distances aromatic rings can recognize each other, a phenomenon that helps explain their importance in protein folding and supramolecular structures.
Keywords:
Aromatization / Calculations / Cyclohexane / Aromatic rings / Aromatic-aromatic interactions / High-level ab initio calculations / Horizontal displacements / Maximum strength / Supramolecular structure / BenzeneSource:
ACS Central Science, 2020, 6, 3, 420-425Publisher:
- American Chemical Society
Funding / projects:
- Noncovalent interactions of pi-systems and their role in molecular recognition (RS-MESTD-Basic Research (BR or ON)-172065)
- Welch Foundation, Grant A-0648, and the National Science Foundation, Grant CHE-1664866.
DOI: 10.1021/acscentsci.0c00005
ISSN: 2374-7943
WoS: 000521935600015
Scopus: 2-s2.0-85081207631
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Hemijski fakultet / Faculty of ChemistryTY - JOUR AU - Ninković, Dragan AU - Blagojević Filipović, Jelena P. AU - Hall, Michael B. AU - Brothers, Edward N. AU - Zarić, Snežana D. PY - 2020 UR - https://cherry.chem.bg.ac.rs/handle/123456789/3946 AB - High-level ab initio calculations show that the most stable stacking for benzene-cyclohexane is 17% stronger than that for benzene-benzene. However, as these systems are displaced horizontally the benzene-benzene attraction retains its strength. At a displacement of 5.0 Å, the benzene-benzene attraction is still ∼70% of its maximum strength, while benzene-cyclohexane attraction has fallen to ∼40% of its maximum strength. Alternatively, the radius of attraction (>2.0 kcal/mol) for benzene-benzene is 250% larger than that for benzene-cyclohexane. Thus, at relatively large distances aromatic rings can recognize each other, a phenomenon that helps explain their importance in protein folding and supramolecular structures. PB - American Chemical Society T2 - ACS Central Science T1 - What Is Special about Aromatic-Aromatic Interactions? Significant Attraction at Large Horizontal Displacement VL - 6 IS - 3 SP - 420 EP - 425 DO - 10.1021/acscentsci.0c00005 ER -
@article{ author = "Ninković, Dragan and Blagojević Filipović, Jelena P. and Hall, Michael B. and Brothers, Edward N. and Zarić, Snežana D.", year = "2020", abstract = "High-level ab initio calculations show that the most stable stacking for benzene-cyclohexane is 17% stronger than that for benzene-benzene. However, as these systems are displaced horizontally the benzene-benzene attraction retains its strength. At a displacement of 5.0 Å, the benzene-benzene attraction is still ∼70% of its maximum strength, while benzene-cyclohexane attraction has fallen to ∼40% of its maximum strength. Alternatively, the radius of attraction (>2.0 kcal/mol) for benzene-benzene is 250% larger than that for benzene-cyclohexane. Thus, at relatively large distances aromatic rings can recognize each other, a phenomenon that helps explain their importance in protein folding and supramolecular structures.", publisher = "American Chemical Society", journal = "ACS Central Science", title = "What Is Special about Aromatic-Aromatic Interactions? Significant Attraction at Large Horizontal Displacement", volume = "6", number = "3", pages = "420-425", doi = "10.1021/acscentsci.0c00005" }
Ninković, D., Blagojević Filipović, J. P., Hall, M. B., Brothers, E. N.,& Zarić, S. D.. (2020). What Is Special about Aromatic-Aromatic Interactions? Significant Attraction at Large Horizontal Displacement. in ACS Central Science American Chemical Society., 6(3), 420-425. https://doi.org/10.1021/acscentsci.0c00005
Ninković D, Blagojević Filipović JP, Hall MB, Brothers EN, Zarić SD. What Is Special about Aromatic-Aromatic Interactions? Significant Attraction at Large Horizontal Displacement. in ACS Central Science. 2020;6(3):420-425. doi:10.1021/acscentsci.0c00005 .
Ninković, Dragan, Blagojević Filipović, Jelena P., Hall, Michael B., Brothers, Edward N., Zarić, Snežana D., "What Is Special about Aromatic-Aromatic Interactions? Significant Attraction at Large Horizontal Displacement" in ACS Central Science, 6, no. 3 (2020):420-425, https://doi.org/10.1021/acscentsci.0c00005 . .
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