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What Is Special about Aromatic–Aromatic Interactions? Significant Attraction at Large Horizontal Displacement
journal contribution
posted on 2020-02-28, 21:33 authored by Dragan
B. Ninković, Jelena P. Blagojević Filipović, Michael B. Hall, Edward N. Brothers, Snežana D. ZarićHigh-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.