Benzoic acid, 2-amino-

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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
Tfus417.8KN/AAndrews, Lynn, et al., 1926Uncertainty assigned by TRC = 0.5 K; with possible decomposition; TRC
Quantity Value Units Method Reference Comment
Δsub104.9 ± 1.0kJ/molVNabavian, Sabbah, et al., 1977Author was aware that data differs from previously reported values; ALS
Δsub104.9 ± 1.0kJ/molVSabbah, Chastelet, et al., 1974ALS
Δsub111.6 ± 1.7kJ/molN/AArnold and Jones, 1972AC

Enthalpy of fusion

ΔfusH (kJ/mol) Temperature (K) Reference Comment
20.5417.8Acree, 1991AC
20.380417.8Andrews, Lynn, et al., 1926, 2DH

Entropy of fusion

ΔfusS (J/mol*K) Temperature (K) Reference Comment
48.8417.8Andrews, 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
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron

View reactions leading to C7H7NO2+ (ion structure unspecified)

Quantity Value Units Method Reference Comment
Proton affinity (review)901.5kJ/molN/AHunter and Lias, 1998HL
Quantity Value Units Method Reference Comment
Gas basicity869.0kJ/molN/AHunter and Lias, 1998HL

Ionization energy determinations

IE (eV) Method Reference Comment
7.6PEMeeks, Wahlborg, et al., 1981LLK
8.29CTSSlifkin and Allison, 1967RDSH
8.0PEMeeks, Wahlborg, et al., 1981Vertical value; LLK

De-protonation reactions

C7H6NO2- + Hydrogen cation = Benzoic acid, 2-amino-

By formula: C7H6NO2- + H+ = C7H7NO2

Quantity Value Units Method Reference Comment
Δr1411. ± 9.2kJ/molG+TSKebarle and McMahon, 1977gas phase; B
Quantity Value Units Method Reference Comment
Δr1382. ± 8.4kJ/molIMREKebarle and McMahon, 1977gas phase; B

References

Go To: Top, Phase change data, Gas phase ion energetics data, Notes

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

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]

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]

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]

Arnold and Jones, 1972
Arnold, P.R.; Jones, F., Polymorphism in Anthranilic Acid Crystals---Examination by DTA and DSC, Molecular Crystals and Liquid Crystals, 1972, 19, 2, 133-140, https://doi.org/10.1080/15421407208083859 . [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]

Slifkin and Allison, 1967
Slifkin, M.A.; Allison, A.C., Measurement of ionization potentials from contact charge transfer spectra, Nature, 1967, 215, 949. [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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