Solvent impact on the aromaticity of benzene analogues: implicit versus explicit solvent approach.
Solvent impact on the structural index of aromaticity was modelled by polarised continuum field approximation (IEFPCM) and hybrid quantum chemistry (QM/MM) method. Significant solvent related relaxation of the solutes geometries were noticed especially for highly polar species. The significant reduction of the aromaticity was observed for some aromatic compounds in water solution compared to gas phase. The rationale of this fact was provided based on dipole moment changes, energy penalty for polarisation of solute and the distribution of frontier orbital densities. The incoherent predictions of explicit and implicit solvation models are noticed since in some cases the PCM approach artificially exaggerate the geometry relaxation in solution which is not observed if explicit solvent molecules are taken into account.
Cysewski
Piotr
P
Department of Physical Chemistry, Collegium Medicum, Nicolaus Copernicus University, Kurpińskiego 5, 85-950 Bydgoszcz, Poland. piotr.cysewski@cm.umk.pl
Szefler
Beata
B
Kozłowska
Katarzyna
K
D000465:Algorithms; D001554:Benzene / Q000737:chemistry*; D007700:Kinetics; D008956:Models, Chemical; D008958:Models, Molecular; D015394:Molecular Structure; D044367:Phase Transition; D011789:Quantum Theory; D012997:Solvents / Q000737:chemistry*; D055672:Static Electricity; D013816:Thermodynamics; D014867:Water / Q000737:chemistry
D012997:Solvents; D014867:Water; D001554:Benzene