Hydrogen Bonding Interactions of m-Chlorotoluene with 1-Alkanol Analyzed by Thermodynamic, Fourier Transform Infrared Spectroscopy, Density Functional Theory, and Natural Bond Orbital

Abstract

Fourier transform infrared spectroscopy (FT-IR) has been employed to obtain information about the nature of interactions in the liquid solutions of pure solvents and their mixtures of m- chlorotoluene (MCT) with 1-alkanol systems at different mole fractions. Furthermore, densities (ρ) and speeds of sound ( u ) of binary mixtures of MCT with a set of five 1-alkanols, namely, 1-propanol, 1-butanol, 1-pentanol, 1-hexanol, and 1-heptanol, were measured as a function of composition at 298.15 K. From the experimental quantities, the excess volumes ( V E ), isentropic compressibility ( k s ), and excess isentropic compressibility ( k s E ) were calculated for the binary mixtures over the entire composition range and under the atmospheric pressure. These excess properties ( V E ) and ( k s E ) were correlated with the Redlich–Kister polynomial equation. Additionally, theoretical density functional theory calculations and natural bond orbital analyses were carried out to further discern the nature and strength of interactions between MCT and 1-alkanols. Moreover, the recorded FT-IR spectra-derived excess properties and quantum chemically derived data revealed the presence of interactions between component molecules in binary liquid solutions.

Intra- and Inter-molecular Interactions between 1-Alkanol and Benzonitrile: Computational and Thermodynamic Study

“…The experimental values of density and speed of sound of samples were determined using Rudolph Research Analytical Digital Densitometer (DDM-2911 model) and single crystal ultrasonic interferometer (model F-05) from Mittal Enterprises, New Delhi, India. In our earlier articles, ,− ultrapure water was used to calibrate the instruments, and we described the details of measurements and calibration of the instruments. The uncertainties were estimated for density and speed of sound measurements within 0.008 g·cm –3 and 2.8 m·s –1 , respectively.…”

Stable catalysis of neutral silica-supported potassium lactate for vapour-phase dehydration of lactic acid to acrylic acid – critical role of the support

“…But when two kinds of organic compound are copresent either in the liquid or the solid phase, their intermolecular interaction via dipolar forces and hydrogen bonding ought to be considered. [82][83][84][85][86] The intermolecular interaction may cause unexpected deviations of the molecular vibrational spectra. 82,[84][85][86] Our IR spectral analysis of a mixture of AA and potassium lactate on KBr shows the presence of an additional band at 1690 cm −1 together with the upward shift of a 1593 cm −1 band to 1600 cm −1 and the shift of other bands (Fig.…”

“…[82][83][84][85][86] The intermolecular interaction may cause unexpected deviations of the molecular vibrational spectra. 82,[84][85][86] Our IR spectral analysis of a mixture of AA and potassium lactate on KBr shows the presence of an additional band at 1690 cm −1 together with the upward shift of a 1593 cm −1 band to 1600 cm −1 and the shift of other bands (Fig. S17 †).…”

Thermodynamic excess functions in organic ternary mixture ‐ Statistical approach (Cibulka expansion)

“…With the approaching electrophile behaviour one of the Hatom of a loop got substituted and the product additionally holds its balance and fragment in nature. [7][8][9][10] Herein, several studies [11,12] have been reported to understand the interaction of 1-alkanols with other organic hydrocarbon liquids via utilizing the U analysis. [12] Further, ternary blends with 1-alkanols as one component are indispensable for the industries to prevent the development of azeotropes in extractive distillation.…”

“…[7][8][9][10] Herein, several studies [11,12] have been reported to understand the interaction of 1-alkanols with other organic hydrocarbon liquids via utilizing the U analysis. [12] Further, ternary blends with 1-alkanols as one component are indispensable for the industries to prevent the development of azeotropes in extractive distillation. The earlier reported literatures show that these studies with higher primary alcohols are not at all available.…”