Abstract
The determination of the reliable thermodynamic properties of 2-benzoxazolinone derivatives is the main goal of this work. Some correlations are established between the energetic properties determined and the structural characteristics of the title compounds, and the reactivity of this class of compounds is also evaluated. Static-bomb combustion calorimetry and high-temperature Calvet microcalorimetry were used to determine, respectively, the standard molar enthalpies of formation in the solid state and the standard molar enthalpies of sublimation, both at T = 298.15 K. Using the results obtained for each compound, the respective gas-phase standard molar enthalpy of formation was derived. High-level quantum chemical calculations were performed to estimate the same property and the results evidence good accordance. Moreover, the gas-phase relative thermodynamic stability of 2-benzoxazolinone derivatives was also evaluated using the respective gas-phase standard molar Gibbs energy of formation. In addition, the relationship between the energetic and structural characteristics of the benzoxazolinones is presented, evidencing the enthalpic increments associated with the presence of a methyl and a nitro groups in the molecule, and this effect is compared with similar ones in other structurally related compounds.
Highlights
Benzoxazolinone (BOA)(BOA)isisa aheterocyclic heterocyclic compound whose structure consists a Benzoxazolinone compound whose structure consists of a of benzene ring ring fusedfused with with a five-membered ring containing oxygenoxygen and nitrogen as heteroatoms.benzene a five-membered ring containing and nitrogen as hetA possible A tautomeric form of BOA is formed result of removal of hydrogen eroatoms.possible tautomeric form of BOAasisaformed asthe a result of the removal offrom hythe nitrogen in the ring of the carbonyl (Figure 1). (FigureThis enol drogen from atom the nitrogen atomtointhe theoxygen ring to the oxygen of thegroup carbonyl group 1).form of BOA is of2-benzoxazolol (Figure 1, (FigureII), energetically much lessmuch stableless than its amide This enol form
∆bustion c u, with the mean value and the corresponding standard deviation of the mean, for the with thecompounds mean valueare and the corresponding standard deviation mean, for the studstudied given in Supplementary
All standard computational calculations were performed using the Gaussian 09 software package [29]. This experimental thermochemical study enabled the determination of new values for the enthalpy of formation, in the crystalline phase, and for the enthalpy of sublimation of two benzoxazolinones
Summary
Benzoxazolinone (BOA)(BOA)isisa aheterocyclic heterocyclic compound whose structure consists a Benzoxazolinone compound whose structure consists of a of benzene ring ring fusedfused with with a five-membered ring containing oxygenoxygen and nitrogen as heteroatoms.benzene a five-membered ring containing and nitrogen as hetA possible A tautomeric form of BOA is formed result of removal of hydrogen eroatoms.possible tautomeric form of BOAasisaformed asthe a result of the removal offrom hythe nitrogen in the ring of the carbonyl (Figure 1). (FigureThis enol drogen from atom the nitrogen atomtointhe theoxygen ring to the oxygen of thegroup carbonyl group 1).form of BOA is of2-benzoxazolol (Figure 1, (FigureII), energetically much lessmuch stableless than its amide This enol form. (BOA)isisa aheterocyclic heterocyclic compound whose structure consists a Benzoxazolinone compound whose structure consists of a of benzene ring ring fusedfused with with a five-membered ring containing oxygenoxygen and nitrogen as heteroatoms. Benzene a five-membered ring containing and nitrogen as hetA possible A tautomeric form of BOA is formed result of removal of hydrogen eroatoms. Possible tautomeric form of BOAasisaformed asthe a result of the removal offrom hythe nitrogen in the ring of the carbonyl (Figure 1). This enol drogen from atom the nitrogen atomtointhe theoxygen ring to the oxygen of thegroup carbonyl group 1). II), energetically much lessmuch stableless than its amide This enol form
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