How to Catch the Ball: Fullerene Binding to the Corannulene Pincer.
Born–Oppenheimer molecular dynamics
buckycatcher–fullerene
semi-empirical
thermodynamics of binding
π stacking
Journal
Molecules (Basel, Switzerland)
ISSN: 1420-3049
Titre abrégé: Molecules
Pays: Switzerland
ID NLM: 100964009
Informations de publication
Date de publication:
15 Jun 2022
15 Jun 2022
Historique:
received:
30
05
2022
revised:
09
06
2022
accepted:
13
06
2022
entrez:
24
6
2022
pubmed:
25
6
2022
medline:
28
6
2022
Statut:
epublish
Résumé
The corannulene pincer (also known in the literature as the buckycatcher) is a fascinating system that may encapsulate, among other molecules, the C60 and C70 fullerenes. These complexes are held together by strong π-stacking interactions. Although these are quantum mechanical effects, their description by quantum chemical methods has proved very hard. We used three semi-empirical methods, PM6-D3H4X, PM6-D3H+ and GFN2-xTB, to model the interactions. Binding to fullerenes was extended to all open conformations of the buckycatcher, and with the proper choice of solvation model and partition functions, we obtained Gibbs free energies of binding that deviated by 1.0-1.5 kcal/mol from the experimental data. Adding three-body dispersion to PM6-D3H+ led to even better agreement. These results agree better with the experimental data than calculations using higher-level methods at a significantly lower fraction of the computational cost. Furthermore, the formation of adducts with C60 was studied using dynamical simulations, which helped to build a more complete picture of the behavior of the corannulene pincer with fullerenes. We also investigated the use of exchange-binding models to recover more information on this system in solution. Though the final Gibbs free energies in solution were worsened, gas-phase enthalpies and entropies better mirrored the experimental data.
Identifiants
pubmed: 35744963
pii: molecules27123838
doi: 10.3390/molecules27123838
pmc: PMC9228874
pii:
doi:
Substances chimiques
Fullerenes
0
Polycyclic Aromatic Hydrocarbons
0
corannulene
0
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Subventions
Organisme : Federal Ministry for Economic Affairs and Energy
ID : KK 5197901TS0
Organisme : Federal Ministry of Education and Research
ID : 031L0268
Références
J Chem Phys. 2019 Apr 21;150(15):154122
pubmed: 31005066
J Chem Theory Comput. 2019 Mar 12;15(3):1652-1671
pubmed: 30741547
J Comput Chem. 2004 Oct;25(13):1605-12
pubmed: 15264254
J Chem Theory Comput. 2012 Jan 10;8(1):141-51
pubmed: 26592877
J Chem Phys. 2010 Apr 21;132(15):154104
pubmed: 20423165
J Chem Phys. 2017 Jul 21;147(3):034112
pubmed: 28734285
Phys Chem Chem Phys. 2010 Jul 14;12(26):7091-7
pubmed: 20517563
J Chem Theory Comput. 2012 Nov 13;8(11):4317-22
pubmed: 26605594
J Mol Model. 2007 Dec;13(12):1173-213
pubmed: 17828561
J Chem Theory Comput. 2015 Aug 11;11(8):3785-801
pubmed: 26574460
J Chem Theory Comput. 2011 Dec 13;7(12):3944-51
pubmed: 26598340
J Cheminform. 2012 Aug 13;4(1):17
pubmed: 22889332
J Chem Theory Comput. 2021 Jul 13;17(7):4250-4261
pubmed: 34185531
J Phys Chem Lett. 2019 Jun 6;10(11):2706-2714
pubmed: 31063380
J Chem Theory Comput. 2013 Mar 12;9(3):1580-91
pubmed: 26587619
PeerJ. 2014 Jun 19;2:e449
pubmed: 25024918
J Am Chem Soc. 2007 Apr 4;129(13):3842-3
pubmed: 17348661
J Chem Theory Comput. 2019 May 14;15(5):2847-2862
pubmed: 30943025
Phys Chem Chem Phys. 2008 May 21;10(19):2813-8
pubmed: 18464998
J Phys Chem B. 2014 Oct 16;118(41):11956-64
pubmed: 25248285
Phys Chem Chem Phys. 2020 Nov 21;22(43):24870-24886
pubmed: 33107520
Chemistry. 2012 Aug 6;18(32):9955-64
pubmed: 22782805
J Mol Model. 2013 Jan;19(1):1-32
pubmed: 23187683
J Chem Phys. 2021 Apr 21;154(15):154104
pubmed: 33887937