Is hydrogen bonding the reason for differences in vapour pressure and vaporisation energetics of optically active and racemic compounds?

Verevkin, Sergey P.

doi:10.1016/j.molliq.2022.119653

Cited by 3 publications

(3 citation statements)

References 15 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…[30] In most cases, the differences between the (RS), (S), and (R) species are small but statistically significant, but the quantitative order is not obvious, and additional studies on the thermodynamics of optically active compounds could contribute to a better understanding of the trends in the (RS), (S), and (R) species as a function of the structure of the chiral compounds. [30] The lesson we have learnt from the studies of chiral compounds is that the differences between the vapour pressures of the racemate and the enantiopure compound are not large and are usually of the same order of magnitude. In this context, it was very surprising that the sublimation vapour pressures of of S-(+)-ibuprofen and RS-(�)-ibuprofen reported by Perlovich et al [11] are very different, as shown in Figure 3.…”

Section: Absolute Vapour Pressuresmentioning

confidence: 99%

“…[29] However, the vapour pressures of (RS)-1-methoxy-2-propanamine, (R)-1methoxy-2-propanamine and (S)-1-methoxy-2-propanamine are essentially the same. [30] In most cases, the differences between the (RS), (S), and (R) species are small but statistically significant, but the quantitative order is not obvious, and additional studies on the thermodynamics of optically active compounds could contribute to a better understanding of the trends in the (RS), (S), and (R) species as a function of the structure of the chiral compounds. [30] The lesson we have learnt from the studies of chiral compounds is that the differences between the vapour pressures of the racemate and the enantiopure compound are not large and are usually of the same order of magnitude.…”

Section: Absolute Vapour Pressuresmentioning

confidence: 99%

“…In a series of our recent works, we have analysed the vapour pressures and vaporization thermodynamics of different groups of optically active compounds. [29][30] For example, the vapour pressures of (S)-1,2-propanediol are significantly smaler than those of the racemate, (RS)-1,2-propanediol. [29] However, the vapour pressures of (RS)-1-methoxy-2-propanamine, (R)-1methoxy-2-propanamine and (S)-1-methoxy-2-propanamine are essentially the same.…”

Section: Absolute Vapour Pressuresmentioning

confidence: 99%

See 2 more Smart Citations

Quantum Chemistry and Pharmacy: Diagnostic Check of the Thermochemistry of Ibuprofen

Emel'yanenko,

Zherikova,

Verevkin

2024

ChemPhysChem

Self Cite

View full text Add to dashboard Cite

The thermodynamic data on ibuprofen available in the literature shows that the disarray of experimental results is unacceptable for this very important drug. The data on ibuprofens available in the literature were collected, combined with our complementary experimental results and evaluated. The enthalpies of combustion and formation of the crystalline RS‐(±)‐ and S‐(+)‐ibuprofens were measured using high‐precision combustion calorimetry. The temperature dependence of the vapour pressure of S‐(+)‐ibuprofen was measured using the transpiration method and the enthalpy of vaporisation was derived from this measurement. The enthalpies of fusion of both compounds were measured using DSC. The G4 calculations have been carried out to determine the enthalpy of formation in gaseous state of the most stable conformer. Thermochemical properties of studied compounds were evaluated and tested for consistency with the “centerpiece approach”. A set of reliable and consistent values of thermodynamic properties of ibuprofens at 298.15 К was recommended for thermochemical calculations of the pharmaceutic processes. The diagnostic protocol was developed to distinguish the “sick” or “healthy” thermodynamic data. This diagnostic is also applicable to other drugs with a different structure than ibuprofen.

show abstract

Section: Absolute Vapour Pressuresmentioning

confidence: 99%