Experimental and Theoretical Studies of Preferential Solvation of 4-Nitroaniline and 4-Nitroanisole in an Amino Acid Ionic Liquid with Molecular Solvents

0520852 - MBÚ 2020 RIV US eng J - Journal Article
Aryafard, Meysam - Jahanshah, M. - Harifi-Mood, A.R. - Minofar, Babak - Kutá Smatanová, Ivana
Experimental and Theoretical Studies of Preferential Solvation of 4-Nitroaniline and 4-Nitroanisole in an Amino Acid Ionic Liquid with Molecular Solvents.
Journal of Chemical and Engineering Data. Roč. 64, č. 12 (2019), s. 5755-5764. ISSN 0021-9568. E-ISSN 1520-5134
Research Infrastructure: CESNET II - 90042; CERIT-SC - 90085
Institutional support: RVO:61388971
Keywords : solvatochromic comparison method * initial configurations * binary-mixtures
OECD category: Biophysics
Impact factor: 2.369, year: 2019
Method of publishing: Limited access
https://pubs.acs.org/doi/pdf/10.1021/acs.jced.9b00719

Amino acid ionic liquids (AAILs) are a new green class of ILs. Maximum wave numbers of 4-nitroaniline and 4-nitroanisole based on the solvatochromic method were calculated in binary mixtures of tetra butyl ammonium glycinate ([N-444][Gly]) with both protic and aprotic molecular solvents to understand the microsphere solvations and preferred solvents. These investigations showed that the effects of glycinate in [N-444][Gly] led to high hydrogen-bond basicity (beta) and polarizabihty (e), and they illustrated that normalized polarity (E-T(N)), pi*, and beta of [N-4444] [Gly] are more than those of molecular solvents. The preferential solvation model presented that the probes prefer to be solvated by either IL or mixed solvents. Molecular dynamic (MD) simulations confirmed the preferential solvation model results and were used to analyze the microsphere solvation of dyes. It has been found out that the glycinate attend the microsphere solvation of 4-nitroaniline to have hydrogen bond interactions with amine group, but the same behavior was not seen for 4nitroanisole. Therefore, shift wavelengths of 4-nitroaniline in binary mixtures are noticeable, which were seen in experimental works. In addition, MD simulations were applied to understand the structural analysis of [N-4444][Gly] and solvent solvent interactions and it showed the distances and good probabilities for hydrogen bond interactions between the glycinate and butanol. Finally, QM calculations confirmed both the experimental and MD simulation findings.
Permanent Link: http://hdl.handle.net/11104/0305512