Thermochemical studies for determination of the molar enthalpy of formation of aniline derivatives

Silva, Manuel A.V. Ribeiro da; Monteiro, Maria F.; Gomes, M.Luı́sa A.C.N.; Chickos, James S.; Smith, Anjanette P.; Liebman, Joel F.

doi:10.1007/bf02275163

Cited by 10 publications

(3 citation statements)

References 15 publications

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“…Probably, this is due to several factors, different from compound to compound, such as the low stability of some amines, the difficulty of achieving high purity state, difficulties of handling of harmful compounds, etc. This is confirmed by experimental research in our group, namely, on the determination of standard enthalpies of formation of dialkylamines and substituted anilines. − …”

Section: Introductionsupporting

confidence: 71%

Solvent and Structural Effects in the N−H Bond Homolytic Dissociation Energy

Gomes

Silva

2004

J. Phys. Chem. A

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In this work, the gas-phase homolytic N−H bond dissociation enthalpy (BDE) was investigated for a large series of molecules containing at least one N−H bond by means of accurate density-functional theory calculations. The molecules studied belong to different classes of compounds, namely, amines, amides and anilines, amino acids, phenoxazines, indolamines, and other compounds of general interest, such as anti-inflammatory drugs. To achieve these purposes, the (RO)B3LYP/6-311+G(2d,2p)//(U)B3LYP/6-31G* level of theory was used. The calculated gas-phase N−H BDEs, at T = 298.15 K, are in the range 499.6−203.9 kJ/mol, for purine and HNO, respectively. Further, the calculated BDEs are in excellent agreement with a significant number of available experimental BDEs. Solvent effects were also taken in account, and rather significant differences are found among N−H BDEs computed in the gas phase and in heptane, DMSO, or water.

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Section: Introductionsupporting

confidence: 71%

Solvent and Structural Effects in the N−H Bond Homolytic Dissociation Energy

Gomes

Silva

2004

J. Phys. Chem. A

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“…Knowledge of the thermochemical properties of benzyl derivatives is necessary to determine the radical stabilization energies and strength of a C-C bond in these compounds (Beckhaus et al, 1990). In recent years considerable activity has taken place with respect to the determination of the enthalpies of formation of amines (Ribeiro da Silva, 1996Steele et al, 1996, Verevkin 1997a1998a;Verevkin et al, 1998) but with limited emphasis on benzyl-substituted species. Thus, a systematical study of the thermochemistry of benzyl derivatives seems to be important for practical and theoretical reasons.…”

Section: Introductionmentioning

confidence: 99%

Strain Effects in Phenyl-Substituted Methanes. Geminal Interaction between Phenyl and the Electron-Releasing Substituent in Benzylamines and Benzyl Alcohols

Verevkin

1999

J. Chem. Eng. Data

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The standard (p° = 0.1 MPa) molar enthalpies of formation Δf H°m(l) at T = 298.15 K of N,N-dimethylbenzylamine, α-methylbenzylamine, and α,α-dimethylbenzylamine were determined by means of combustion calorimetry. The standard molar enthalpies of vaporization of these compounds and also of benzylamine, benzyl alcohol, and α,α-dimethylbenzyl alcohol were obtained from the temperature dependence of the vapor pressure measured in a flow system. Resulting values of Δf H°m(g) were obtained at T = 298.15 K and used to derive strain enthalpies of benzyl derivatives. The intramolecular interactions of the substituents were discussed in terms of deviations of Δf H°m(g) from the group additivity rules. These values provide a further improvement on the group-contribution methodology for estimation of the thermodynamic properties of organic compounds.

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“…Mean value (122.4 ± 1.5) a,b a The uncertainly assigned to the mean value is standard deviation of the mean. b Mean value calculated excluding equation (55).…”

Section: Discussionmentioning

confidence: 99%

Experimental and computational energetic study of 1-R-2-phenylindole (R = H, CH3, C2H5)

Carvalho

Amaral

Morais

et al. 2015

The Journal of Chemical Thermodynamics

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Thermochemical studies for determination of the molar enthalpy of formation of aniline derivatives

Abstract: The standard (p~ --0.1 MPa) molar enthalpies of combustion at T = 298.15 K were measured by static bomb combustion calorimetry for liquid N, N-diethylaniline, N,N-dimethyl-m-toluidine, N,N-dimethyl-p-toluidine, and N-ethyl-m-

Cited by 10 publications

References 15 publications

Solvent and Structural Effects in the N−H Bond Homolytic Dissociation Energy

Solvent and Structural Effects in the N−H Bond Homolytic Dissociation Energy

Strain Effects in Phenyl-Substituted Methanes. Geminal Interaction between Phenyl and the Electron-Releasing Substituent in Benzylamines and Benzyl Alcohols

Experimental and computational energetic study of 1-R-2-phenylindole (R = H, CH3, C2H5)

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