Benzoic acid, 4-amino-, methyl ester

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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
AC - William E. Acree, Jr., James S. Chickos

Quantity Value Units Method Reference Comment
Tfus384.3KN/AManzo and Ahumanda, 1990Uncertainty assigned by TRC = 0.5 K; TRC
Tfus385.1KN/ANeau, Flynn, et al., 1989Uncertainty assigned by TRC = 0.5 K; TRC
Tfus385.7KN/ASchwartz and Paruta, 1976Uncertainty assigned by TRC = 0.5 K; TRC
Tfus385.KN/AYalkowsky, Flynn, et al., 1972Uncertainty assigned by TRC = 1. K; TRC

Enthalpy of fusion

ΔfusH (kJ/mol) Temperature (K) Reference Comment
22.55385.1Manzo and Ahumada, 1990AC

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

Quantity Value Units Method Reference Comment
Proton affinity (review)883.9kJ/molN/AHunter and Lias, 1998HL
Quantity Value Units Method Reference Comment
Gas basicity853.0kJ/molN/AHunter and Lias, 1998HL

Ionization energy determinations

IE (eV) Method Reference Comment
7.7PEMeeks, Wahlborg, et al., 1981LLK
8.08 ± 0.01EIFoffani, Pignataro, et al., 1964RDSH
8.1PEMeeks, Wahlborg, et al., 1981Vertical value; LLK

Appearance energy determinations

Ion AE (eV) Other Products MethodReferenceComment
C7H6NO+10.91CH3OEIHowe and Williams, 1969RDSH

De-protonation reactions

C8H8NO2- + Hydrogen cation = Benzoic acid, 4-amino-, methyl ester

By formula: C8H8NO2- + H+ = C8H9NO2

Quantity Value Units Method Reference Comment
Δr1475. ± 8.8kJ/molG+TSTaft and Topsom, 1987gas phase; value altered from reference due to change in acidity scale; B
Quantity Value Units Method Reference Comment
Δr1444. ± 8.4kJ/molIMRETaft and Topsom, 1987gas phase; value altered from reference due to change in acidity scale; 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.

Manzo and Ahumanda, 1990
Manzo, R.H.; Ahumanda, A.A., Effects of solvent medium on solubility. V: Enthalpic and entropic contributions to the free energy changes of Di-substituted benzene derivatives in ethanol: Water and ethanol: Cyclohexane mixtures, J. Pharm. Sci., 1990, 79, 12, 1109, https://doi.org/10.1002/jps.2600791214 . [all data]

Neau, Flynn, et al., 1989
Neau, S.H.; Flynn, G.L.; Yalkowsky, S.H., Int. J. Pharm., 1989, 49, 223. [all data]

Schwartz and Paruta, 1976
Schwartz, P.A.; Paruta, A.N., Solution thermodynamics of alkyl p-aminobenzoates, J. Pharm. Sci., 1976, 65, 252. [all data]

Yalkowsky, Flynn, et al., 1972
Yalkowsky, S.H.; Flynn, G.L.; Slunick, T.G., Importance of chain length on physicochemical and crystalline properties of organic homologs, J. Pharm. Sci., 1972, 61, 852. [all data]

Manzo and Ahumada, 1990
Manzo, Ruben H.; Ahumada, Amelia A., Effects of solvent medium on solubility. V: Enthalpic and entropic contributions to the free energy changes of Di-substituted benzene derivatives in ethanol: Water and ethanol: Cyclohexane mixtures, J. Pharm. Sci., 1990, 79, 12, 1109-1115, https://doi.org/10.1002/jps.2600791214 . [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]

Foffani, Pignataro, et al., 1964
Foffani, A.; Pignataro, S.; Cantone, B.; Grasso, F., Ionization potentials and substituent effects for aromatic carbonyl compounds, Z. Physik. Chem. (Frankfurt), 1964, 42, 221. [all data]

Howe and Williams, 1969
Howe, I.; Williams, D.H., Calculation and qualitative predictions of mass spectra. Mono- and paradisubstituted benzenes, J. Am. Chem. Soc., 1969, 91, 7137. [all data]

Taft and Topsom, 1987
Taft, R.W.; Topsom, R.D., The Nature and Analysis of Substituent Effects, Prog. Phys. Org. Chem., 1987, 16, 1. [all data]


Notes

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