2014
DOI: 10.1002/jcc.23644
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Interaction between ions and substituted buckybowls: A comprehensive computational study

Abstract: Complexes formed by substituted buckybowls derived from corannulene and sumanene with sodium cation or chloride anion have been computationally studied by using a variety of methods. Best results have been obtained with the SCS-MP2 method extrapolated to basis set limit, which reproduces the highest-level values obtained with the MP2.X method. All bowls form stable complexes with chloride anion, with stabilities ranging from -6 kcal/mol in the methylated corannulene derivative to -45 kcal/mol in the CN-substit… Show more

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Cited by 18 publications
(36 citation statements)
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“…Corannulene has a bowl depth amounting to 0.86 Å, in agreement with previous calculations and the X‐ray structure . Sumanene is a deeper bowl, with a depth of 1.11 Å to the carbon atoms in the rim of the hexagonal rings (0.86 Å to the pentagonal rings), also in agreement with previous results in the literature . The inclusion of sulphur atoms in sumanene to give sumaS leads to a significant flattening of the bowl, reducing the depth to just 0.68 Å.…”
Section: Resultssupporting
confidence: 90%
See 1 more Smart Citation
“…Corannulene has a bowl depth amounting to 0.86 Å, in agreement with previous calculations and the X‐ray structure . Sumanene is a deeper bowl, with a depth of 1.11 Å to the carbon atoms in the rim of the hexagonal rings (0.86 Å to the pentagonal rings), also in agreement with previous results in the literature . The inclusion of sulphur atoms in sumanene to give sumaS leads to a significant flattening of the bowl, reducing the depth to just 0.68 Å.…”
Section: Resultssupporting
confidence: 90%
“…The bowl asymmetry is clearly revealed by the molecular electrostatic potentials (MEPs) plotted in Figure , showing the MEPs from below (convex face) and from above (concave face) the bowls, varying from −15 (red) to 15 (blue) kcal/mol on isodensity surfaces of 0.002 a.u. As in previous work, corannulene and sumanene have negative MEP on the central region of both sides of the bowl, although slightly more negative on the convex face. While corannulene shows a negative surface inside the bowl and positive on the rim, in sumanene the negative surface of the convex side is disrupted by positive regions corresponding to the CH 2 groups.…”
Section: Resultssupporting
confidence: 84%
“…Comparing entries 1 and 2 in Table 3, the effect of dispersion on the geometries turns out to be quantitatively not that relevant, by less than 1 kcal/mol. In comparison with previous results of the interaction of cations with carbon-based structures [33], MP2 and CCSD [34] give more favourable interactions of the potassium ion with the empty carbo-benzene by 3.0 and 0.4 kcal/mol only, respectively, taking into account the energy values in solution. Moreover, the intermolecular basis set superposition error (BSSE) is not very relevant since it is just 0.9 kcal/mol with potassium ion, for the 6-311G(d,p) basis set.…”
Section: Resultsmentioning
confidence: 59%
“…5,7 The same could be said of the hydrogen bond-like interactions between X-H groups and aromatic rings, mostly involving OH, NH and CH bonds. 8,10 Finally, the interaction between aromatic rings and charged species is controlled by the combination of electrostatic and induction contributions in cation···π contacts, 9,[11][12][13][14] whereas the role of induction is less significant when anions are involved. 14,15 In any case, the interaction between a cation and a polarisable π cloud is usually strong in the gas phase, being a contact frequently observed in biological systems.…”
Section: A Introductionmentioning
confidence: 99%
“…8,10 Finally, the interaction between aromatic rings and charged species is controlled by the combination of electrostatic and induction contributions in cation···π contacts, 9,[11][12][13][14] whereas the role of induction is less significant when anions are involved. 14,15 In any case, the interaction between a cation and a polarisable π cloud is usually strong in the gas phase, being a contact frequently observed in biological systems. [16][17][18][19][20] However, the strength of the cation···π interactions can be modulated by changes on the environment or on the nature of the aromatic ring involved.…”
Section: A Introductionmentioning
confidence: 99%