Benzoic acid, 3-amino-

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Gas phase thermochemistry data

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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Data compiled by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Quantity Value Units Method Reference Comment
Δfgas-69.15 ± 0.86kcal/molCcrNabavian, Sabbah, et al., 1977Author was aware that data differs from previously reported values

Phase change data

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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Data compiled as indicated in comments:
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
AC - William E. Acree, Jr., James S. Chickos
DH - Eugene S. Domalski and Elizabeth D. Hearing

Quantity Value Units Method Reference Comment
Tfus452.9KN/AAndrews, Lynn, et al., 1926Uncertainty assigned by TRC = 0.6 K; accompanied by some decomposition; TRC
Quantity Value Units Method Reference Comment
Δsub30.59 ± 0.76kcal/molVSabbah, Chastelet, et al., 1974ALS
Δsub30.6 ± 0.76kcal/molCSabbah, Chastel, et al., 1974See also Nabavian, Sabbah, et al., 1977, 2.; AC

Enthalpy of sublimation

ΔsubH (kcal/mol) Temperature (K) Method Reference Comment
29.2 ± 0.2374.8TEde Kruif, Voogd, et al., 1979AC
29.2 ± 0.7367. to 389.CSabbah, Chastel, et al., 1974AC

Enthalpy of fusion

ΔfusH (kcal/mol) Temperature (K) Reference Comment
8.05445.7Rotich, Glass, et al., 2001AC
5.220452.9Acree, 1991AC
5.2199452.9Andrews, Lynn, et al., 1926, 2DH

Entropy of fusion

ΔfusS (cal/mol*K) Temperature (K) Reference Comment
11.5452.9Andrews, Lynn, et al., 1926, 2DH

In addition to the Thermodynamics Research Center (TRC) data available from this site, much more physical and chemical property data is available from the following TRC products:


Gas phase ion energetics data

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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Data evaluated as indicated in comments:
HL - Edward P. Hunter and Sharon G. Lias

Data compiled as indicated in comments:
B - John E. Bartmess
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi

View reactions leading to C7H7NO2+ (ion structure unspecified)

Quantity Value Units Method Reference Comment
Proton affinity (review)206.7kcal/molN/AHunter and Lias, 1998HL
Quantity Value Units Method Reference Comment
Gas basicity198.9kcal/molN/AHunter and Lias, 1998HL

Ionization energy determinations

IE (eV) Method Reference Comment
7.8PEMeeks, Wahlborg, et al., 1981LLK
8.4 ± 0.2EIBenoit, 1973LLK
8.3PEMeeks, Wahlborg, et al., 1981Vertical value; LLK

Appearance energy determinations

Ion AE (eV) Other Products MethodReferenceComment
C6H6N+14.3 ± 0.2CO+OHEIBenoit, 1973LLK
C7H6NO+12.2 ± 0.2OHEIBenoit, 1973LLK

De-protonation reactions

C7H6NO2- + Hydrogen cation = Benzoic acid, 3-amino-

By formula: C7H6NO2- + H+ = C7H7NO2

Quantity Value Units Method Reference Comment
Δr341.5 ± 2.1kcal/molG+TSKebarle and McMahon, 1977gas phase; B
Quantity Value Units Method Reference Comment
Δr334.5 ± 2.0kcal/molIMREKebarle and McMahon, 1977gas phase; B

References

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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Nabavian, Sabbah, et al., 1977
Nabavian, P.M.; Sabbah, R.; Chastel, R.; Laffitte, M., Thermodynamique de composes azotes. II. Etude thermochimique des acides aminobenzoiques, de la pyrimidine, de l'uracile et de la thymine., J. Chim. Phys., 1977, 74, 115-126. [all data]

Andrews, Lynn, et al., 1926
Andrews, D.H.; Lynn, G.; Johnston, J., The Heat Capacities and Heat of Crystallization of Some Isomeric Aromatic Compounds, J. Am. Chem. Soc., 1926, 48, 1274. [all data]

Sabbah, Chastelet, et al., 1974
Sabbah, R.; Chastelet, R.; Laffitte, M., Thermodynamic de composès azotes. I. Etude calorimètrique des enthalpies de sublimation des trios acides aminobenzoïques, Can. J. Chem., 1974, 52, 2201. [all data]

Sabbah, Chastel, et al., 1974
Sabbah, Raphaël; Chastel, Raymond; Laffitte, Marc, Thermodynamique de composés azotés. I. Etude calorimétrique des enthalpies de sublimation des trois acides aminobenzoïques, Can. J. Chem., 1974, 52, 12, 2201-2205, https://doi.org/10.1139/v74-319 . [all data]

Nabavian, Sabbah, et al., 1977, 2
Nabavian, M.; Sabbah, R.; Chastel, R.; Laffitte, M., J. Chim. Phys.Phys.-Chim. Biol., 1977, 74, 115. [all data]

de Kruif, Voogd, et al., 1979
de Kruif, C.G.; Voogd, J.; Offringa, J.C.A., Enthalpies of sublimation and vapour pressures of 14 amino acids and peptides, The Journal of Chemical Thermodynamics, 1979, 11, 7, 651-656, https://doi.org/10.1016/0021-9614(79)90030-2 . [all data]

Rotich, Glass, et al., 2001
Rotich, M.K.; Glass, B.D.; Brown, M.E., Journal of Thermal Analysis and Calorimetry, 2001, 64, 2, 681-688, https://doi.org/10.1023/A:1011584125859 . [all data]

Acree, 1991
Acree, William E., Thermodynamic properties of organic compounds: enthalpy of fusion and melting point temperature compilation, Thermochimica Acta, 1991, 189, 1, 37-56, https://doi.org/10.1016/0040-6031(91)87098-H . [all data]

Andrews, Lynn, et al., 1926, 2
Andrews, D.H.; Lynn, G.; Johnston, J., The heat capacities and heat of crystallization of some isomeric aromatic compounds, J. Am. Chem. Soc., 1926, 48, 1274-1287. [all data]

Hunter and Lias, 1998
Hunter, E.P.; Lias, S.G., Evaluated Gas Phase Basicities and Proton Affinities of Molecules: An Update, J. Phys. Chem. Ref. Data, 1998, 27, 3, 413-656, https://doi.org/10.1063/1.556018 . [all data]

Meeks, Wahlborg, et al., 1981
Meeks, J.; Wahlborg, A.; McGlynn, S.P., Photoelectron spectroscopy of carbonyls: Benzoic acid and its derivatives, J. Electron Spectrosc. Relat. Phenom., 1981, 22, 43. [all data]

Benoit, 1973
Benoit, F., Substituent effects in mass spectrometry. III. Substituent effects in the dissociation of the molecular ions of para and meta subtituted benzoic acids, Org. Mass Spectrom., 1973, 7, 295. [all data]

Kebarle and McMahon, 1977
Kebarle, P.; McMahon, T.B., Intrinsic Acidities of Substituted Phenols and Benzoic Acids Determined by Gas Phase Proton Transfer Equilibria, J. Am. Chem. Soc., 1977, 99, 7, 2222, https://doi.org/10.1021/ja00449a032 . [all data]


Notes

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