Jacobowsky and the Colonel

Smith, Winifred; Werfel, Franz

doi:10.2307/40084803

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“…To the best of our knowledge the enthalpies of combustion of 2-bromo-and 2-iodoethanol in the liquid state have never been determined, and the ∆ c H m o values reported for 2-chloroethanol 62,63 (which are not mentioned in major thermochemical compilations) 6,7,64 1), although not within the uncertainty interval. These authors also mention that the shaking bomb method by Popoff and Shirokich tends to give less exothermic enthalpies of combustion for organochlorine compounds with high Cl content.…”

Section: Resultsmentioning

confidence: 97%

“…These authors also mention that the shaking bomb method by Popoff and Shirokich tends to give less exothermic enthalpies of combustion for organochlorine compounds with high Cl content. 63 In 68,69 were used to calculate the enthalpies of the isodesmic and isogyric reactions in Table 2. Also indicated in that table are the corresponding values obtained by the B3LYP/cc-pVTZ and CBS-QB3 methods and the deviations ∆…”

Section: Resultsmentioning

confidence: 99%

“…To the best of our knowledge the enthalpies of combustion of 2-bromo- and 2-iodoethanol in the liquid state have never been determined, and the Δ c values reported for 2-chloroethanol , (which are not mentioned in major thermochemical compilations) ,, are essentially of historical value. In 1933 Popoff and Shirokich proposed Δ c (ClCH 2 CH 2 OH, l) = −1191.4 ± 1.2 kJ·mol -1 at 288 K, on the basis of four combustion experiments performed with a shaking bomb combustion calorimeter .…”

Section: Resultsmentioning

confidence: 99%

“…A decade later, using a rotating-bomb combustion calorimeter, Smith and Sunner reported Δ c (ClCH 2 CH 2 OH, l) = −1214.0 ± 1.2 kJ·mol -1 at 298.15 K, a value that is close to the result obtained in this work (Table ), although not within the uncertainty interval. These authors also mention that the shaking bomb method used by Popoff and Shirokich tends to give less exothermic enthalpies of combustion for organochlorine compounds with high Cl content …”

Section: Resultsmentioning

confidence: 99%

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Energetics of C−F, C−Cl, C−Br, and C−I Bonds in 2-Haloethanols. Enthalpies of Formation of XCH₂CH₂OH (X = F, Cl, Br, I) Compounds and of the 2-Hydroxyethyl Radical

Bernardes

Piedade²,

Amaral³

et al. 2007

J. Phys. Chem. A

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The energetics of the C-F, C-Cl, C-Br, and C-I bonds in 2-haloethanols was investigated by using a combination of experimental and theoretical methods. The standard molar enthalpies of formation of 2-chloro-, 2-bromo-, and 2-iodoethanol, at 298.15 K, were determined as Delta(f)H(degree)m(CH2CH2OH, l) = -315.5 +/- 0.7 kJ.mol-1, Delta(f)H(degree)mBrCH2CH2OH, l) = -275.8 +/- 0.6 kJ.mol-1, Delta(f)H(degree)m(ICH2CH2OH, l) = -207.3 +/- 0.7 kJ.mol-1, by rotating-bomb combustion calorimetry. The corresponding standard molar enthalpies of vaporization, Delta(vap)H(degree)m(ClCH2CH2OH) = 48.32 +/- 0.37 kJ.mol-1, Delta(vap)H(degree)m(BrCH2CH2OH) = 54.08 +/- 0.40 kJ.mol-1, and Delta(vap)H(degree)m(ICH2CH2OH) = 57.03 +/- 0.20 kJ.mol-1 were also obtained by Calvet-drop microcalorimetry. The condensed phase and vaporization enthalpy data lead to Delta(f)H(degree)m(ClCH2CH2OH, g) = -267.2 +/- 0.8 kJ.mol-1, Delta(f)H(degree)m(BrCH2CH2OH, g) = -221.7 +/- 0.7 kJ.mol-1, and Delta(f)H(degree)m(ICH2CH2OH, g) = -150.3 +/- 0.7 kJ.mol-1. These values, together with the enthalpy of selected isodesmic and isogyric gas-phase reactions predicted by density functional theory (B3LYP/cc-pVTZ) and CBS-QB3 calculations were used to derive the enthalpies of formation of gaseous 2-fluoroethanol, Delta(f)H(degree)m(FCH2CH2OH, g) = -423.6 +/- 5.0 kJ.mol-1, and of the 2-hydroxyethyl radical, Delta(f)H(degree)m(CH2CH2OH, g) = -28.7 +/- 8.0 kJ.mol-1. The obtained thermochemical data led to the following carbon-halogen bond dissociation enthalpies: DHo(X-CH2CH2OH) = 474.4 +/- 9.4 kJ.mol-1 (X = F), 359.9 +/- 8.0 kJ.mol-1 (X = Cl), 305.0 +/- 8.0 kJ.mol-1 (X = Br), 228.7 +/- 8.1 kJ.mol-1 (X = I). These values were compared with the corresponding C-X bond dissociation enthalpies in XCH2COOH, XCH3, XC2H5, XCH=CH2, and XC6H5. In view of this comparison the computational methods mentioned above were also used to obtain Delta(f)H(degree)m-594.0 +/- 5.0 kJ.mol-1 from which DHo(F-CH2COOH) = 435.4 +/- 5.4 kJ.mol-1. The order DHo(C-F) > DHo(C-Cl) > DHo(C-Br) > DHo(C-I) is observed for the haloalcohols and all other RX compounds. It is finally concluded that the major qualitative trends exhibited by the C-X bond dissociation enthalpies for the series of compounds studied in this work can be predicted by Pauling's electrostatic-covalent model.

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Section: Resultsmentioning

confidence: 97%

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

See 2 more Smart Citations

Energetics of C−F, C−Cl, C−Br, and C−I Bonds in 2-Haloethanols. Enthalpies of Formation of XCH₂CH₂OH (X = F, Cl, Br, I) Compounds and of the 2-Hydroxyethyl Radical

Bernardes

Piedade²,

Amaral³

et al. 2007

J. Phys. Chem. A

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Jacobowsky and the Colonel

Cited by 1 publication

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Energetics of C−F, C−Cl, C−Br, and C−I Bonds in 2-Haloethanols. Enthalpies of Formation of XCH₂CH₂OH (X = F, Cl, Br, I) Compounds and of the 2-Hydroxyethyl Radical

Energetics of C−F, C−Cl, C−Br, and C−I Bonds in 2-Haloethanols. Enthalpies of Formation of XCH₂CH₂OH (X = F, Cl, Br, I) Compounds and of the 2-Hydroxyethyl Radical

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Jacobowsky and the Colonel

Cited by 1 publication

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Energetics of C−F, C−Cl, C−Br, and C−I Bonds in 2-Haloethanols. Enthalpies of Formation of XCH2CH2OH (X = F, Cl, Br, I) Compounds and of the 2-Hydroxyethyl Radical

Energetics of C−F, C−Cl, C−Br, and C−I Bonds in 2-Haloethanols. Enthalpies of Formation of XCH2CH2OH (X = F, Cl, Br, I) Compounds and of the 2-Hydroxyethyl Radical

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Energetics of C−F, C−Cl, C−Br, and C−I Bonds in 2-Haloethanols. Enthalpies of Formation of XCH₂CH₂OH (X = F, Cl, Br, I) Compounds and of the 2-Hydroxyethyl Radical

Energetics of C−F, C−Cl, C−Br, and C−I Bonds in 2-Haloethanols. Enthalpies of Formation of XCH₂CH₂OH (X = F, Cl, Br, I) Compounds and of the 2-Hydroxyethyl Radical