Thermochemistry of substituted benzenes: quantification of ortho-, para-, meta-, and buttress interactions in alkyl-substituted nitrobenzenes

Verevkin, Sergey P.; Heintz, Andreas

doi:10.1006/jcht.2000.0589

Cited by 17 publications

(9 citation statements)

References 23 publications

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“…Verevkin and Heintz have reported p sat data for 2-NT in the same temperature range that we measured. Their data, which cover the temperature range (274 to 323) K, also were measured with a gas saturation method, although many of the experimental details differ from the current study .…”

Section: Resultssupporting

confidence: 76%

“…The mononitrotoluenes are a typical case. Vapor pressure data are available for 2-nitrotoluene (2-NT), 3-nitrotoluene (3-NT), and 4-nitrotoluene (4-NT), but almost all of the data are for temperatures above 323 K. − At lower temperatures, there is only one set of data for 2-NT and one set of data for 4-NT . No vapor pressures for 3-NT have been reported in this temperature range.…”

Section: Introductionmentioning

confidence: 99%

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Gas Saturation Vapor Pressure Measurements of Mononitrotoluene Isomers from (283.15 to 313.15) K

Widegren

Bruno

2009

J. Chem. Eng. Data

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A gas saturation apparatus capable of simultaneous measurements on 18 samples was used for this work. The vapor pressures of 2-nitrotoluene (2-NT), 3-nitrotoluene (3-NT), 4-nitrotoluene (4-NT), and tetradecane (a control compound) were measured with this apparatus over the temperature range (283.15 to 313.15) K. Over this temperature range, the vapor pressure of 2-NT ranged from (5.53 to 61.1) Pa; the vapor pressure of 3-NT ranged from (3.39 to 37.8) Pa; and the vapor pressure of 4-NT ranged from (1.25 to 26.4) Pa. The enthalpies of vaporization or sublimation were determined using the Clausius−Clapeyron equation.

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Section: Resultssupporting

confidence: 76%

Section: Introductionmentioning

confidence: 99%

Gas Saturation Vapor Pressure Measurements of Mononitrotoluene Isomers from (283.15 to 313.15) K

Widegren

Bruno

2009

J. Chem. Eng. Data

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“…Only for 28 and 55 we can suggest that experimental and calculated Δ f H 298 °(g) values disagree due to the experimental error in the enthalpy of sublimation. Experimental data for 16 reported in two works 49,54 are very different from each other; however, the experimental values by Verevkin and Heintz 49 are in much better agreement with the theoretical result. It should be noted that an examination of closely related species provides additional evidence of a possible small error in the experimental enthalpies of formation of 16, 21, 23, 28, 31, 33, 55, 57, 65, 71−73, 77, and 95.…”

Section: Resultsmentioning

confidence: 55%

Use of G4 Theory for the Assessment of Inaccuracies in Experimental Enthalpies of Formation of Aromatic Nitro Compounds

Suntsova

Дорофеева

2015

J. Chem. Eng. Data

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The gas-phase enthalpies of formation (Δ f H 298 °) of 101 aromatic nitro compounds were calculated using the Gaussian-4 (G4) theory applied to the atomization and isodesmic reaction energies. The Δ f H 298 °(g) values calculated from the atomization reactions were underestimated by an average of 13 kJ•mol −1 and they could not be used for the assessment of inaccuracies in the experimental enthalpies of formation. A good agreement with the most available experimental data was obtained using the isodesmic reaction procedure. From 5 to 26 isodesmic reactions with different reference species were constructed for each compound. About 15 aliphatic nitro compounds and 100 different C/H/N/O/Cl compounds were used as the reference species in these reactions; the accuracy of enthalpies of formation of all reference compounds was preliminarily confirmed by theoretical calculations. Evidence of accuracy of experimental data was provided by the agreement with calculated values. The differences between the calculated and the experimental enthalpies of formation in the range from (8 to 46) kJ•mol −1 were assigned to possible errors in the experimental values for 21 compounds. The theoretical Δ f H 298 °(g) values were recommended for these compounds as being more reliable than the experimental values. On the basis of theoretical results, a reference data set of internally consistent gas-phase enthalpies of formation of aromatic nitro compounds was provided. Both experimental and calculated values are included in this data set. The recommended Δ f H 298 °(g) values of aromatic nitro compounds are consistent with each other and with Δ f H 298 °(g) values of about 115 different C/H/N/O/Cl compounds including aliphatic nitro compounds. More accurate condensed phase enthalpies of formation and enthalpies of sublimation (or vaporization) were recommended in some cases based on a critical analysis of reported experimental data supplemented by quantum chemical calculations.

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“…A fairly large number of papers have been published on the vapor pressures of NTs [18,26,[32][33][34][35][36][37][38]. The data from those papers [18,26,38], that present vapor pressure data for temperatures below 60 8C is shown in Figure 3. As has been mentioned above, the vapor pressures for 4-NT in the paper by Lenchitz and Velicky [26] are erroneous, and Figure 3 only shows the corrected data.…”

Section: Nitrotoluenesmentioning

confidence: 99%

Vapor Pressure of Explosives: A Critical Review

Östmark

Wallin

Ang

2012

Propellants Explo Pyrotec

196

151

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A critical review of vapor pressure data for military, civilian, and homemade explosives, explosive precursors, and explosive taggants is presented. It gives reference to a large number of papers and reports presenting original vapor pressure measurements and additionally an overview of measurements techniques for vapor pressure measurements and data analysis of vapor pressure measurements. Vapor pressure data, including Clausius–Clapeyron parameters (A and B in: log10(p)=A−B/T), calculated vapor pressure at room temperature, and heat of sublimation or heat of vaporization are included. The following classes of compounds are treated; military explosives (TNT, RDX, HMX, PETN, HNS, TATB, AP), civilian explosives (NG, EGDN, AN), explosive taggants (EGDN, DNMB, 2‐NT, 4‐NT), home‐made explosives (TATP, DADP, HMTD). and explosive precursors [HP(aq), NM, IPN, DNT].

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Thermochemistry of substituted benzenes: quantification of ortho-, para-, meta-, and buttress interactions in alkyl-substituted nitrobenzenes

Cited by 17 publications

References 23 publications

Gas Saturation Vapor Pressure Measurements of Mononitrotoluene Isomers from (283.15 to 313.15) K

Gas Saturation Vapor Pressure Measurements of Mononitrotoluene Isomers from (283.15 to 313.15) K

Use of G4 Theory for the Assessment of Inaccuracies in Experimental Enthalpies of Formation of Aromatic Nitro Compounds

Vapor Pressure of Explosives: A Critical Review

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