Enthalpies of combustion of di-n-propylamine, diisopropylamine, diisobutylamine, and di-sec-butylamine

Silva, Manuel A.V. Ribeiro da; Gomes, M.Luı́sa A.C.N.; Johnson, Mathew; Pilcher, G.

doi:10.1006/jcht.1997.0219

Cited by 10 publications

(6 citation statements)

References 6 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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“…As estimated previously (7) from group energy contributions, this enthalpic difference should correspond to 99.3 kJ · mol −1 . On the other hand, a simple difference between the corresponding standard molar enthalpies of formation in the gaseous phase (23) yields a difference of (108 ± 3) kJ · mol −1 , well in accordance with the experimental difference found for the pair of thioureas reported in this paper, (110 ± 8) kJ · mol −1 .…”

Section: Discussionsupporting

confidence: 88%

A calorimetric study of N, N-diethyl-N′-furoylthiourea and N, N-diisobutyl-N′-furoylthiourea

Silva

Dietze

2002

The Journal of Chemical Thermodynamics

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“…38 We accordingly stated that we felt that the experimental value is incorrect. A new experimental value was subsequently determined and reported, 75 and is used for comparison in this work. Indeed, this error has now been diminished to À0.10 kcal/mol.…”

Section: Heats Of Formationmentioning

confidence: 99%

Molecular mechanics (MM4) study of amines

et al. 2007

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The MM4 force field has been extended to include aliphatic amines. About 20 amines have been examined to obtain a set of useful molecular mechanics parameters for this class. The vibrational spectra of seven amines (172 frequencies) calculated by MM4 have an overall rms error of 27 cm(-1), compared with corresponding MM4 value of 24 cm(-1) for alkanes. The rms and signed average errors of the moments of inertia of nine simple amines compared with the experimental data were 0.18% and -0.004%, respectively. The heats of formation of 30 amines were also studied. The MM4 weighted standard deviation is 0.41 kcal/mol, compared with experiment. Electronegativity effects occur in the hydrocarbon portion of an amine from the nitrogen, and are accounted for by including electronegativity induced changes in bond lengths and angles, and induced dipole-dipole interactions in the molecule. Negative hyperconjugation results from the presence of the lone pair of electrons on nitrogen, and leads to the Bohlmann bands in the infrared, and also to strong and unusual geometric changes in the molecules (Bohlmann effect), all of which are fairly well accounted for. The conformational energies in amines appear to be less straightforward than those for most other classes of molecules, apparently because of the Bohlmann effect, and these are probably not yet completely understood. In general, the agreement between the MM4 calculated results and the available data is reasonably good.

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Enthalpies of combustion of di-n-propylamine, diisopropylamine, diisobutylamine, and di-sec-butylamine

Cited by 10 publications

References 6 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

A calorimetric study of N, N-diethyl-N′-furoylthiourea and N, N-diisobutyl-N′-furoylthiourea

Molecular mechanics (MM4) study of amines

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