Effect of solvent on the volumetric behavior of N,N′-salicylidenephenyl diamine (Salophen) Schiff base at different temperatures (288.15–318.15) K
Introduction
Schiff bases, discovered by Hugo Schiff, are a nitrogen analog of an aldehyde or ketone in which the carbonyl group (CO) has been replaced by an imine or azomethine group (CHN) [1]. These compounds are often obtained in good yield and high purity through a straightforward synthetic procedure. Many Schiff bases and Schiff base complexes show some interesting properties, such as fluorescence [2], luminescence [3], and photochromic [4]. Schiff bases have other specifications, such as antifungal, antimicrobial, antiviral, antitumor, plant growth regulation, and dying applications [5], [6]. These compounds can be used to produce conducting polymers, optical materials [7], [8], [9], and pH sensors [10]. Among them, N,N′-salicylidenephenyl diamine Schiff bases (Salophen) are being considered as potential catalysts [11] and can be used in chemical reactions.
Generalized usages of Schiff bases and their complexes need an accurate knowledge of their thermodynamic properties when they are mixed with other compounds. Volumetric properties of mixtures can provide valuable information about solute–solvent and solute–solute interactions in solution. Therefore, in this work, the volumetric properties of Salophen Schiff base in some organic solvents, dimethylsulfoxide (DMSO), N,N-dimethylacetamide (DMA), 1,4-dioxacyclohexane (1,4-dioxane), and oxolane (THF), have been investigated. Apparent molar volumes () of Salophen Schiff base were calculated at T = (288.15–318.15) K and used to estimate the standard partial molar volumes (), standard partial molar isobaric expansivity (), Hepler's constant , and isobaric thermal expansion coefficient (α). Furthermore, the values of the interaction volumes (Vint), and cavity volumes (Vcav) were estimated using scaled particle theory. All of these parameters were used to interpret various solute–solute and solute–solvent interactions occurring between the components in binary mixtures.
Section snippets
Chemicals
Reagents used in this work were salicylaldehyde, benzene-1,2-diamine, DMSO, DMA, 1,4-dioxane, and THF which their sources and purity are tabulated in Table 1. Density (d), viscosity (η), and refractive index (nD) of the solvents along with their literature values at 298.15 K are given in Table 2.
Synthesis of N,N′-salicylidenephenyl diamine (Salophen) Schiff base
A mixture of benzene-1,2-diamine (10 mmol) in 40 mL of ethanol was added dropwise to a vigorously stirred ethanolic mixture (40 mL) of salicylaldehyde (20 mmol). After the addition was complete, the mixture
Results and discussion
Densities (d) of binary mixtures containing Salophen Schiff base + organic solvents (DMSO, DMA, 1,4-dioxane, and THF) and the calculated apparent molar volumes () at different temperatures (288.15–318.15) K are reported in Table 3. The apparent molar volumes () of Salophen Schiff base in the organic solvents were obtained from the densities of the mixtures using the following equation:where, M is the molar mass of the Salophen Schiff base, m is the molality of the Schiff
Conclusions
Densities of Salophen Schiff base + organic solvent (DMSO, DMA, 1,4-dioxane, and THF) binary mixtures have been measured at T = (288.15–318.15) K. Using these data, the standard partial molar volumes (), standard partial molar isobaric expansivities (), isobaric thermal expansion coefficients (α), and Hepler's constants of the mixtures at different temperatures have been calculated. The values of interaction volume (Vint), and cavity volume (Vcav) have also been estimated using
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