Thermochemical study of anthranilate derivatives: Effect of the size of the alkyl substituent

Freitas, Vera L.S.; Silva, Carlos A. O.; Silva, Manuel A.V. Ribeiro da

doi:10.1016/j.jct.2021.106441

Cited by 4 publications

(3 citation statements)

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“…Computational thermochemistry was used to study the thermodynamic properties of the four methyl methylanthranilate (MMA) isomers in the gas phase: MMA-3, MMA-4, MMA-5, and MMA-6. The G3(MP2)//B3LYP composite method [ 15 ] was employed for this purpose, as it has exhibited exceptional performance in previous studies [ 9 , 16 , 17 ]. A conformational analysis was developed to identify and quantify the various stable conformations for each isomer of MMAs.…”

Section: Resultsmentioning

confidence: 99%

“…This work is part of a broader research project that aims to determine the thermodynamic properties of key fragrance classes. The inherent goal is to reduce existing gaps and contribute to the improvement of estimation methods for environmental risk assessment [ 7 , 8 , 9 ]. A comprehensive comparative analysis of the thermodynamic properties of methyl methylanthranilate (MMA) isomers is presented.…”

Section: Introductionmentioning

confidence: 99%

“…The G3(MP2)//B3LYP absolute enthalpies and the experimental gas-phase enthalpies of formation of all the auxiliary compounds are reported in TableS5of Supplementary Materials[9,[20][21][22][23][24][25];2 The uncertainty assigned corresponds to the expanded uncertainty determined from the estimated standard deviation of the mean for seven reactions (H1-H7) and the coverage factor k = 2.5 (0.95 level of confidence and six degrees of freedom)[26].…”

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confidence: 99%

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Determination and Analysis of Thermodynamic Properties of Methyl Methylanthranilate Isomers

Silva,

Freitas,

da Silva

2023

Molecules

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The enthalpies of formation in the gaseous phase of methyl 3-methylanthranilate and methyl 5-methylanthranilate were determined from experimental measurements of the corresponding standard energies of combustion, obtained from combustion calorimetry, and the standard enthalpies of vaporization and sublimation, obtained from Calvet microcalorimetry and Knudsen mass-loss effusion. A computational study, using the G3(MP2)//B3LYP composite method, has also been performed for the calculation of the gas-phase standard enthalpies of formation of those two molecules at T = 298.15 K, as well as for the remaining isomers, methyl 4-methylanthranilate and methyl 6-methylanthranilate. The results have been used to evaluate and analyze the energetic effect of the methyl substituent in different positions of the ring.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

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Determination and Analysis of Thermodynamic Properties of Methyl Methylanthranilate Isomers

Silva,

Freitas,

da Silva

2023

Molecules

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Thermochemical study to assess the energetical and structural effects of nitro substituents in methyl benzoate isomers

Ledo

Flores

Ramos

et al. 2022

The Journal of Chemical Thermodynamics

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Phase Transition Enthalpy Measurements of Organic Compounds. An Update of Sublimation, Vaporization, and Fusion Enthalpies from 2016 to 2021

Acree

Chickos

2022

Journal of Physical and Chemical Reference Data

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The compendium of phase change enthalpies published in two parts in 2016 is updated to include new fusion, vaporization, and sublimation enthalpies published in the interim and includes some earlier data either previously missed or were unavailable. Also included in this article is an update of recent studies on the phase change enthalpies of polyaromatic hydrocarbons. Group values previously evaluated to adjust for temperature of phase changes are updated for aromatic compounds in view of recent experimental data. The new group parameters have been evaluated on the basis of their consistency in providing appropriate temperature adjustments to phase change enthalpies at T = 298 K as evaluated by a thermochemical cycle. This evaluation provides transition temperatures and about 1000 heats of fusion, 700 heats of vaporization, 500 heats of sublimation, and about 50 other heats of transitions for about 30 polyaromatic hydrocarbons and 1100 other molecules consisting of C1-C57 organic compunds, organometallics, inorganic compounds, and ionic liquids taken from about 900 references.

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Thermochemical study of anthranilate derivatives: Effect of the size of the alkyl substituent

Cited by 4 publications

References 29 publications

Determination and Analysis of Thermodynamic Properties of Methyl Methylanthranilate Isomers

Determination and Analysis of Thermodynamic Properties of Methyl Methylanthranilate Isomers

Thermochemical study to assess the energetical and structural effects of nitro substituents in methyl benzoate isomers

Phase Transition Enthalpy Measurements of Organic Compounds. An Update of Sublimation, Vaporization, and Fusion Enthalpies from 2016 to 2021

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