Solvatochromism of isatin based Schiff bases: An LSER and LFER study

Abstract

The derivatives of isatin have already been reported to show a variety of biological activities. However, there has been no report on solvatochromic effect of isatin derivatives so far, and that could be of interest to study and relate to their electronic structure, as a part of the characterisation of these compounds. Linear solvation energy relationships (LSER) were used to analyze solvent influence on the UV absorption maxima shifts of investigated isatin derivatives, i.e. isatin based Schiff bases, by using Kamlet-Taft model. Linear free energy relationships (LFER) were applied to the substituent-induced NMR chemical shifts (SCS) using SSP (single substituent parameter). The obtained correlations together with theoretical calculations gave insight into the influence of the molecular conformation on the transmission of substituent effects, as well as on solute/solvent interactions. The molecular electrostatic potential (MEP) surface map was plotted over the optimized geometry of the molecules in order to visualize electron density distribution and explain origin of solvent/solute interactions. [Projekat Ministarstva nauke Republike Srbije, br. 172013]

Detailed solvent, structural, quantum chemical study and antimicrobial activity of isatin Schiff base

“…General method applied for sixteen isatin derivatives preparation, is presented on Fig. 1 and described in Supplementary material [17]. The list of synthesized compounds and their elemental analysis are given in Table S3, while FTIR data in Table S4.…”

“…Electronic properties of the isomeric forms of investigated isatin sensitively depends on solvent properties like polarity, stabilization of the charges in the solvation sphere and alteration of a solute's electronic structure in the ground and excited state due to both short-and longrange interactions with surrounding solvent molecules [17,39]. Additionally, geometries and substituent effects on the extent/intensity of solvent/solute interactions could be of appropriate significance.…”

“…In our previous study, LSER and LFER and quantum-chemical calculations related to isatin derivatives [17] were performed. In this work sixteen compounds were synthesized (Fig.…”

Experimental and theoretical study on solvent and substituent effects on the intramolecular charge transfer in 3-[(4-substituted)phenylamino]isobenzofuran-1(3H)-ones

“…12,18,20 One of the general concepts concerning the relationship between molecular structure and absorption spectrum leads to conclusion that the existence of planarity in the molecular geometry produces higher bathochromic shifts in the UV-Vis spectra due to increased π-conjugation throughout the investigated molecules. 21 In order to study the influence of solvent-solute interactions on the absorption maxima, the UV-Vis spectra of ten synthesized 3-[(4-substituted)phenylamino]isobenzofuran-1(3H)-ones were recorded in sixteen solvents of different properties. Characteristic spectra in dichloromethane and methanol are shown as examples in Fig.…”

Preferential solvation of quercetin in aqueous aprotic solvent mixtures

“…Therefore, the solvatochromic signals convey direct information about the nature of solute-solvent interactions, which can be used to characterize properties and structure of a solvent in the presence of a solute. [1][2][3][4][5][6][7][8][9][10][11][12][13][14][15][16][17] In a pure solvent, the solvent composition is the same for both bulk and solvation shell regions. However, the arrangement of solvent molecules can be varied around the solute, due to solute-solvent interactions, depending on the nature of a solute and solvent.…”