Thermodynamic properties of some isomeric 5-(nitrophenyl)-furyl-2 derivatives

Volodymyr Dibrivnyi,Yuriy Horak,Lubomyr Goshko,Mykola Obushak,Andriy Marshalek,Nadiia Velychkivska,Iryna Sobechko

doi:10.1186/s13065-019-0619-2

Abstract

BackgroundThe aim of the current work was to determine thermodynamical properties of 5-(nitrophenyl)-2-furaldehyde oximes and 3-[5-(nitrolphenyl)-2-furyl]acrylic acids.ResultsThe temperature dependences of saturated vapor pressures of 5-(nitrophenyl)-2-furaldehyde oximes and 3-[5-(nitrolphenyl)-2-furyl]acrylic acids were determined by the Knudsen effusion method. The results are presented by the Clapeyron–Clausius equation in linear form, and via this form, the standard enthalpies of sublimation of compounds were calculated at 298.15 K. The standard molar formation enthalpies of compounds in crystalline state at 298.15 K were determined indirectly from the corresponding standard molar combustion enthalpy, obtained using combustion bomb calorimetry. The non-nearest neighbour interactions (strain) in molecule were defined. The ideal-gas enthalpies of investigated compounds formation and the data available from the literature were used for calculation of group-additivity parameters and the correction terms useful in the application of the Benson correlation.ConclusionDetermining the thermodynamic properties for these compounds will contribute to solving practical problems pertaining to optimization processes of their synthesis, purification and application. It will also provide a more thorough insight regarding the theoretical knowledge of their nature and are necessary for the application of the Benson group-contribution correlation for calculation of Delta {}_{f}H_{{m(298.15{text{K}})}}^{o} (g)calc.

Highlights

The rapid growth of pharmaceutical and chemical industries using nitrogen-containing heterocyclic compounds requires a continuous diversification of these products
The measurement results were processed by the least squares method and presented as a linear equation: lnP (Pa) = A + B/T with correlation coefficient ρ, by means of which the standard molar enthalpies gcrHmo ( T ) = B·R were calculated at average temperatures of measurement interval T (Table 3)
For the acids D, E, F the minimum internal energy of the molecules is observed when the chain of atoms –CH=CH–C(O)–OH is in a plane almost perpendicular to the furan cycle plane

Summary

Introduction

The rapid growth of pharmaceutical and chemical industries using nitrogen-containing heterocyclic compounds requires a continuous diversification of these products. New synthesized compounds with complex structure have no description of their thermodynamic properties. Numerous reactions of synthesis of nitrogencontaining compounds with a phenyl furan fragment, which exhibit various types of biological activity, have been investigated. This allows them to be widely used in various fields of medical chemistry [1–10]. The furfural oximes are used as inhibitors of soil nitrification [1], as intermediates in the synthesis of anti-TB [11] and antifungal [12] drugs, and as starting materials for the synthesis of disubstituted derivatives of furan [13]. Phenyl derivatives of furfural oxime show antispasmodic [14], vasodilator [15], cardiotropic [8] and antiviral [9] properties. The aim of the current work was to determine thermodynamical properties of 5-(nitrophenyl)-2-furaldehyde oximes and 3-[5-(nitrolphenyl)-2-furyl]acrylic acids

Objectives

Results

Conclusion