Thermochemical properties of sesquiterpenes in natural products by correlation gas chromatography: Application to bergamotene oil

Orf, Megan; Kurian, Manu; Espinosa, Lorna; Nelson, Carissa; Simmons, Dan; Chickos, James S.

doi:10.1016/j.jct.2018.06.017

Cited by 19 publications

(27 citation statements)

References 22 publications

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“…c An average of eight runs, four from this work, plus, four from reference [10]. d An average of six runs, four from this work, plus, two from reference [11].…”

Section: Vapor Pressuresmentioning

confidence: 97%

“…The presence of β-bisabolene in both opopanax oils was identified and confirmed by co-injection with a sample from a different supplier [11]; α trans-bergamotene was identified similarly. Gas chromatograms of the two opopanax oils used in this study are provided as Figures S1 and S2 c Source: B-94/8 Joshi colony I. P. Extn, Patpar Ganj Delhi 110,092 India; identified by GCMS and the NIST/EPA/NIH MS library [10].…”

Section: Compounds: Identity and Purity Controlsmentioning

confidence: 99%

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Vaporization Enthalpies and Vapor Pressures of the Major Components of Opopanax Oil, α-Santalene, cis α Bisabolene, cis α-Bergamotene,

Barton

Chickos

2021

Preprint

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The vapor pressures and vaporization enthalpies of the major components of opopanax oil, a medicinal that has been in use since biblical times, are evaluated by correlation gas chromatography. Two sets of hydrocarbon standards are used, n-alkanes and a mixture of cyclic and polycyclic hydrocarbons. Two of the oil’s sesquiterpene components, evaluated in a previous study, were used both as standards and also as targets. Their use as targets was in an effort to confirm both their identity in the oil and the reproducibility of their properties. All correlations produce reproducible vaporization enthalpies and vapor pressures at ambient temperatures. At elevated temperatures, the use of the two different sets of standards resulted in some divergence in vapor pressure. Experiments are described aimed at attenuating this divergence. The results are compared to existing data.

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“…c An average of eight runs, four from this work, plus, four from reference [10]. d An average of six runs, four from this work, plus, two from reference [11].…”

Section: Vapor Pressuresmentioning

confidence: 97%

Section: Compounds: Identity and Purity Controlsmentioning

confidence: 99%

Vaporization Enthalpies and Vapor Pressures of the Major Components of Opopanax Oil, α-Santalene, cis α Bisabolene, cis α-Bergamotene,

Barton

Chickos

2021

Preprint

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“…Our laboratory has been investigating the use of a technique referred to a correlation gas chromatography to evaluate both vaporization enthalpies and vapor pressures of materials that are either difficult to access, or beyond the current capabilities of most conventional techniques used for these purposes. This includes substances that are present in complex mixtures [5,6], are either quite non-volatile [7], or as in this case, available only in very small quantities [8]. This work describes our results for (±) N-ethylamphetamine whose structure is given in Figure 1 along with the materials used as standards.…”

Section: Introductionmentioning

confidence: 93%

The Vaporization Enthalpy and Vapor Pressure of (±) N-Ethyl Amphetamine by Correlation Gas Chromatography

Chickos

2021

Molecules

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The vaporization enthalpy, and vapor pressure as a function of temperature of N-ethylamphetamine, a substance used in the 1950s as an appetite suppressant and more currently abused as a designer drug, is reported. Its physical properties are compared to those of S (+)-N-methamphetamine, a substance whose physiological properties it mimics. A vaporization enthalpy of (62.4 ± 4.4) kJ·mol−1 and vapor pressure of (19 ± 11) Pa at T = 298.15 K has been evaluated by correlation gas chromatography. Results are compared to estimated values and to the limited amount of experimental property data available.

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“…Further collective sources have been used to complement—and compare—the experimental data [ 8 , 14 , 15 , 23 , 24 , 25 , 26 , 27 , 28 , 29 , 30 ]. In addition, vapour-pressure data have been published specifically for various saturated and unsaturated hydrocarbons [ 31 , 32 , 33 , 34 , 35 , 36 , 37 , 38 , 39 , 40 , 41 , 42 , 43 , 44 , 45 , 46 , 47 , 48 , 49 , 50 , 51 , 52 ], alcohols [ 53 , 54 , 55 , 56 , 57 , 58 ], phenols [ 59 , 60 ], alkyl- and arylethers [ 61 , 62 , 63 , 64 ], acetals [ 65 , 66 ], carboxylic acids [ 67 , 68 , 69 , 70 , 71 ], carboxylic halides […”

Section: Sources Of Vapor-pressure Datamentioning

confidence: 99%

Calculation of the Vapour Pressure of Organic Molecules by Means of a Group-Additivity Method and Their Resultant Gibbs Free Energy and Entropy of Vaporization at 298.15 K

Naef

Acree

2021

Molecules

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The calculation of the vapour pressure of organic molecules at 298.15 K is presented using a commonly applicable computer algorithm based on the group-additivity method. The basic principle of this method rests on the complete breakdown of the molecules into their constituting atoms, further characterized by their immediate neighbour atoms. The group contributions are calculated by means of a fast Gauss–Seidel fitting algorithm using the experimental data of 2036 molecules from literature. A ten-fold cross-validation procedure has been carried out to test the applicability of this method, which confirmed excellent quality for the prediction of the vapour pressure, expressed in log(pa), with a cross-validated correlation coefficient Q2 of 0.9938 and a standard deviation σ of 0.26. Based on these data, the molecules’ standard Gibbs free energy ΔG°vap has been calculated. Furthermore, using their enthalpies of vaporization, predicted by an analogous group-additivity approach published earlier, the standard entropy of vaporization ΔS°vap has been determined and compared with experimental data of 1129 molecules, exhibiting excellent conformance with a correlation coefficient R2 of 0.9598, a standard error σ of 8.14 J/mol/ K and a medium absolute deviation of 4.68%.

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Thermochemical properties of sesquiterpenes in natural products by correlation gas chromatography: Application to bergamotene oil

Cited by 19 publications

References 22 publications

Vaporization Enthalpies and Vapor Pressures of the Major Components of Opopanax Oil, α-Santalene, cis α Bisabolene, cis α-Bergamotene,

Vaporization Enthalpies and Vapor Pressures of the Major Components of Opopanax Oil, α-Santalene, cis α Bisabolene, cis α-Bergamotene,

The Vaporization Enthalpy and Vapor Pressure of (±) N-Ethyl Amphetamine by Correlation Gas Chromatography

Calculation of the Vapour Pressure of Organic Molecules by Means of a Group-Additivity Method and Their Resultant Gibbs Free Energy and Entropy of Vaporization at 298.15 K

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