Standard enthalpies of combustion of five halogen-substituted 8-hydroxyquinolines by rotating-bomb calorimetry

Silva, Manuel A.V. Ribeiro da; Ferrão, Maria Luı́sa C.C.H.; Silva, Adelina M.R.O. Alves da

doi:10.1006/jcht.1995.0065

Cited by 24 publications

(9 citation statements)

References 9 publications

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“…Results from this source, however, are not universally consistent, as shown by Verevkin et al, 175 who demonstrated that the enthalpies of combustion for 1,3-and 1,4-diiodobenzene reported by Smith 117 are inconsistent by more than 20 kJ mol 21 , which far exceeds the expected experimental uncertainty of a few kilojoules per mole. We concur with the recommendation of Ribeiro da Silva et al 118 that additional research into the thermodynamics of iodine-containing compounds is needed.…”

Section: Discussionsupporting

confidence: 89%

“…An exception is the result reported for 2chlorobenzoic acid by Holdiness, 96 who used a commercial calorimeter (Parr Instrument Company) with the static bomb (instead of commonly required rotating bomb) and determined an enthalpy of combustion that is ;0.5% more positive than those reported by other researchers [97][98][99] (as expected because of an incomplete reaction or dissolution of gases). The most recent version of the Parr bomb calorimeter 100 has an associated expanded uncertainty for a measured enthalpy of, at least, 0.6%, which corresponds to an expanded The two values reported by Ribeiro da Silva et al 81,118 were determined with a static (first value) and rotating bomb calorimeter (second value), respectively. The difference between these values is 1.8 kJ mol 21 .…”

Section: Enthalpies Of Combustion and Formationmentioning

confidence: 99%

“…The value of D c H o m (cr) reported by Holdiness deviates by 2% from all other values, and this deviation converts to a 60 kJ mol 21 difference in the enthalpy of formation. A variety of calorimeters were used in the consistent results, including static bomb calorimetry, 81,117,118 rotating-bomb calorimetry, 81,118 and rocking micro-calorimetry. 115,119 Values reported by Smith 117 in 1956 were recalculations of those reported in the thesis by Karlsson.…”

Section: Enthalpies Of Combustion and Formationmentioning

confidence: 99%

“…For 2-chlorobenzoic acid, the results of Smith et al 97 are only slightly low relative to those of Johnson and Prosen 94 and Sabbah and Rojas Aguilar. 99 Nonetheless, we have removed the results of Smith et al 97 (Table 9), which is slightly higher than those by Smith 117 and Ribeiro da Silva et al 118 and was not included in the weighted average.…”

Section: Experimental Sources Of Enthalpies Of Sublimationmentioning

confidence: 99%

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Critical Evaluation of Thermodynamic Properties for Halobenzoic Acids Through Consistency Analyses for Results from Experiment and Computational Chemistry

Chirico

Kazakov

Bazyleva

et al. 2017

Journal of Physical and Chemical Reference Data

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Thermodynamic properties of the twelve monohalobenzoic acids are critically evaluated through the application of computational chemistry methods for the ideal-gas phase and thermodynamic consistency assessment of properties determined experimentally and reported in the literature, including enthalpies of combustion, enthalpies of sublimation, and enthalpies of fusion. The compounds of interest are the 2-, 3-, and 4-halo isomers of fluoro-, chloro-, bromo-, and iodobenzoic acids. Computations were validated by comparison with critically evaluated entropies and heat capacities in the ideal-gas state for benzoic acid, benzene, and some halobenzenes. Experimental enthalpies of formation for 2-and 3-bromobenzoic acids, measured by well-established research groups, are mutually inconsistent and further, are shown to be inconsistent with the computations and assessment in this work. Origins of the discrepancies are unknown, and recommended values for these compounds are based on computations and enthalpies of sublimation validated, in part, by a structure-property (i.e., group-additivity) analysis. Lesser, but significant, inconsistencies between experimental and computed results are demonstrated also for 3-and 4-iodobenzoic acids. The comparison of enthalpies of formation based on the experiment and computation for the ideal-gas state of 1-and 2-chloro-, bromo-, and iodonaphthalenes provides additional support for the findings for halobenzoic acids and also reveals some anomalous results in the experimental literature for chloronaphthalenes. Computations are discussed in detail to demonstrate the approach required to obtain optimal results with modern quantum chemical methods.

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Section: Discussionsupporting

confidence: 89%

Section: Enthalpies Of Combustion and Formationmentioning

confidence: 99%

Section: Enthalpies Of Combustion and Formationmentioning

confidence: 99%

Section: Experimental Sources Of Enthalpies Of Sublimationmentioning

confidence: 99%

See 2 more Smart Citations

Critical Evaluation of Thermodynamic Properties for Halobenzoic Acids Through Consistency Analyses for Results from Experiment and Computational Chemistry

Chirico

Kazakov

Bazyleva

et al. 2017

Journal of Physical and Chemical Reference Data

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“…Combustion Calorimetry. The isoperibol rotating-bomb combustion calorimeter used in this work has been described …”

Section: Methodsmentioning

confidence: 99%

Energetics of the C−Cl Bond in CH₃CH(Cl)COOH. Enthalpy of Formation of (S)-(−)-2-Chloropropionic Acid and of the 1-Carboxyethyl Radical^,

Lagoa¹,

Diogo²,

Piedade³

et al. 2002

J. Phys. Chem. A

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The energetics of the C-Cl bond in 2-chloropropionic acid was investigated by using a combination of experimental and theoretical methods. The standard molar enthalpy of formation of liquid (S)-(-)-2chloropropionic acid, at 298.15 K, was determined as ∆ f H°m(C 3 H 5 O 2 Cl, l) ) -( 534.6 ( 1.1) kJ‚mol -1 , by rotating-bomb combustion calorimetry. The corresponding enthalpy of vaporization, ∆ vap H°m(C 3 H 5 O 2 Cl) ) (64.9 ( 0.5) kJ‚mol -1 , was also obtained from vapor pressure versus temperature measurements by the transpiration method, leading to ∆ f H°m(C 3 H 5 O 2 Cl, g) ) -(469.7 ( 1.2) kJ‚mol -1 . This value, together with the enthalpy of the isodesmic and isogyric gas-phase reaction CH 3 CH(X)COOH(g) + C 2 H 5 (g) f CH 3 CHCOOH(g) + C 2 H 5 X(g) (X ) H, Cl) predicted by density functional theory calculations and other auxiliary data, was used to derive the enthalpy of formation of the gaseous 1-carboxyethyl radical as ∆ f H°m[CH(CH 3 )COOH, g] ) -( 293( 3) kJ‚mol -1 , from which DH°[H-CH(CH 3 )COOH] ) 380.7 ( 3.9 kJ‚mol -1 and DH°[Cl-CH(CH 3 )COOH] ) 298.0 ( 3.2 kJ‚mol -1 were obtained. These values are compared with the corresponding C-H and C-Cl bond dissociation enthalpies in XCH 2 COOH, XCH 3 , XC 2 H 5 , XCH 2 -Cl, XCH(CH 3 )Cl, XCHdCH 2 , and XC 6 H 5 (X ) H, Cl). The order DH°(C-H) > DH°(C-Cl) is observed for the carboxylic acids and all other RX compounds. Comparison of DH°[X-CH(CH 3 )COOH] and DH°[X-CH 2 COOH] (X ) H, Cl) indicates that the replacement of a hydrogen of the CH 2 group of XCH 2 COOH by a methyl group leads to a decrease of both the C-H and C-Cl bond dissociation enthalpy. It is finally concluded that the major qualitative trends exhibited by the C-Cl bond dissociation enthalpies for the series of compounds addressed in this work can be predicted based on Pauling's electrostatic-covalent model. † Part of the special issue "Jack Beauchamp Festschrift". ‡ This article is dedicated to Professor Jack L. Beauchamp on the occasion of his 60th birthday.

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Energetics of C−Cl, C−Br, and C−I Bonds in Haloacetic Acids: Enthalpies of Formation of XCH2COOH (X=Cl, Br, I) Compounds and the Carboxymethyl Radical

Lagoa¹,

Diogo²,

Dias³

et al. 2001

Chem. Eur. J.

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The standard molar enthalpies of formation of chloro-, bromo-, and iodoacetic acids in the crystalline state, at 298.15 K, were determined as deltafH(o)m(C2H3O2Cl, cr alpha)=-(509.74+/- 0.49) kJ x mol(-1), deltafH(o)m(C2H3O2Br, cr I)-(466.98 +/- 1.08) kJ x mol(-1), and deltafH(o)m (C2H3O2I, cr)=-(415.44 +/- 1.53) kJ x mol(-1), respectively, by rotating-bomb combustion calorimetry. Vapor pressure versus temperature measurements by the Knudsen effusion method led to deltasubH(o)m(C2H3O2Cl)=(82.19 +/- 0.92) kJ x mol(-1), deltasubH(o)m(C2H3O2Br)=(83.50 +/- 2.95) kJ x mol(-1), and deltasubH(o)m-(C2H3O2I) = (86.47 +/- 1.02) kJ x mol(-1), at 298.15 K. From the obtained deltafH(o)m(cr) and deltasubH(o)m values it was possible to derive deltafH(o)m(C2H3O2Cl, g)=-(427.55 +/- 1.04) kJ x mol(-1), deltafH(o)m (C2H3O2Br, g)=-(383.48 +/- 3.14) kJ x mol(-1), and deltafH(o)m(C2H3O2I, g)=-(328.97 +/- 1.84) kJ x mol(-1). These data, taken with a published value of the enthalpy of formation of acetic acid, and the enthalpy of formation of the carboxymethyl radical, deltafH(o)m(CH2COOH, g)=-(238 +/- 2) kJ x mol(-1), obtained from density functional theory calculations, led to DHo(H-CH2COOH)=(412.8 +/- 3.2) kJ x mol(-1), DHo(Cl-CH2COOH)=(310.9 +/- 2.2) kJ x mol(-1), DHo(Br-CH2COOH)=(257.4 +/- 3.7) kJ x mol(-1), and DHo(I-CH2COOH)=(197.8 +/- 2.7) kJ x mol(-1). A discussion of the C-X bonding energetics in XCH2COOH, CH3X, C2H5X, C2H3X, and C6H5X (X=H, Cl, Br, I) compounds is presented.

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Standard enthalpies of combustion of five halogen-substituted 8-hydroxyquinolines by rotating-bomb calorimetry

Cited by 24 publications

References 9 publications

Critical Evaluation of Thermodynamic Properties for Halobenzoic Acids Through Consistency Analyses for Results from Experiment and Computational Chemistry

Critical Evaluation of Thermodynamic Properties for Halobenzoic Acids Through Consistency Analyses for Results from Experiment and Computational Chemistry

Energetics of the C−Cl Bond in CH₃CH(Cl)COOH. Enthalpy of Formation of (S)-(−)-2-Chloropropionic Acid and of the 1-Carboxyethyl Radical^,

Energetics of C−Cl, C−Br, and C−I Bonds in Haloacetic Acids: Enthalpies of Formation of XCH2COOH (X=Cl, Br, I) Compounds and the Carboxymethyl Radical

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Standard enthalpies of combustion of five halogen-substituted 8-hydroxyquinolines by rotating-bomb calorimetry

Cited by 24 publications

References 9 publications

Critical Evaluation of Thermodynamic Properties for Halobenzoic Acids Through Consistency Analyses for Results from Experiment and Computational Chemistry

Critical Evaluation of Thermodynamic Properties for Halobenzoic Acids Through Consistency Analyses for Results from Experiment and Computational Chemistry

Energetics of the C−Cl Bond in CH3CH(Cl)COOH. Enthalpy of Formation of (S)-(−)-2-Chloropropionic Acid and of the 1-Carboxyethyl Radical,

Energetics of C−Cl, C−Br, and C−I Bonds in Haloacetic Acids: Enthalpies of Formation of XCH2COOH (X=Cl, Br, I) Compounds and the Carboxymethyl Radical

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Energetics of the C−Cl Bond in CH₃CH(Cl)COOH. Enthalpy of Formation of (S)-(−)-2-Chloropropionic Acid and of the 1-Carboxyethyl Radical^,