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DOI: 10.1039/C8NJ02520G
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implemented in the GABEDIT software, secondly at the Hartree- 11. L. Zhou, E. Al-Zaini and A. A. Adesina, Fuel, 2013, 103, 617-625.
Fock/6-31+G* level of theory and, finally, at the B3LYP functional 12. C. Chiappe, S. Rajamani and F. D'Andrea, Green Chem., 2013,
2
3
using 6-31+G* basis set with the D3BJ correction in the ORCA
15, 137-143.
.0.1.2 software. IPBE were calculated using structures optimized 13. C. M. Breneman and K. B. Wiberg, J. Comput. Chem., 1990, 11,
in the TPSS-D3/6-311++G(3df,3dp) level, using structures from 361-373.
B3LYP-D3 as inputs. The resolution of identity approximation (Split- 14. J. Rigby and E. I. Izgorodina, Phys. Chem. Chem. Phys., 2013, 15,
RI-J as implemented in ORCA) was used in the TPSS-D3 calculations 1632-1646.
in order to speed up the process. IPBE were also counterpoise 15. R. G. Pearson, Coord. Chem. Rev., 1990, 100, 403-425.
2
4
4
2
5
corrected using a previous procedure. Tight conversion settings 16. R. G. Parr, L. v. Szentpaly and S. Liu, J. Am. Chem. Soc., 1999,
were used in all calculations as implemented in ORCA. The initial 121, 1922-1924.
guess of the molecular orbitals stem from the PMODEL method, as 17. P. K. Chattaraj, S. Giri and S. Duley, Chem. Rev., 2011, 111,
implemented in ORCA. Vibrational frequency calculations were PR43-PR75.
performed in the final optimized structures to certify the minimum 18. S. Zahn, D. R. MacFarlane and E. I. Izgorodina, Phys. Chem.
local state in the potential energy surface. Most of the final Chem. Phys., 2013, 15, 13664-13675.
structures have no imaginary frequencies associated to them, with 19. G. Klopman, J. Am. Chem. Soc., 1968, 90, 223-234.
the exception of [Hmim][TsO] at the B3LYP-D3/6-31+G* level, which 20. B. S. Samant and M. G. Sukhthankar, Bioorg. Med. Chem. Lett.,
-
1
has a imaginary frequency at 5.89 cm , but since this is such a small
value, the structure was considered to be valid. The frontier orbital 21. Q. Su, S. Ioannidis, C. Chuaqui, L. Almeida, M. Alimzhanov, G.
2011, 21, 1015-1018.
energies, CHELPG charges and bond distances for the reaction
descriptors were calculated in single point runs at B3LYP-D3/6-
Bebernitz, K. Bell, M. Block, T. Howard, S. Huang, D. Huszar, J. A.
Read, C. R. Costa, J. Shi, M. Su, M. Ye and M. Zinda, J. Med.
Chem., 2014, 57, 144-158.
31+G* level of theory in ORCA. Molecular electrostatic potential
maps (MEPs) of total electronic densities using the partial charges 22. A. R. Allouche, J. Comput. Chem., 2011, 32, 174-182.
were calculated at the B3LYP-D3/6-31+G* level using the Gabedit 23. S. Grimme, S. Ehrlich and L. Goerigk, J. Comput. Chem., 2011,
software. The isosurface value used was 0.016803 with grid values
32, 1456-1465.
from -0.09 to 0.09. Details on the equations used to calculate the 24. F. Neese, WIREs Comput. Mol. Sci., 2018, 8, e1327.
descriptors, as well as all optimized structures can be found in the 25. S. F. Boys and F. Bernardi, Mol. Phys., 1970, 19, 553-566.
supporting information.
Conflicts of interest
There are no conflicts to declare.
Acknowledgements
The authors thank the following Brazilian agencies for financial
support: CAPES, CNPq (449758/2014-1) and FAPERGS (16/2551-
0000373-4).
Notes and references
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