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 (kcal/mol) Temperature (K) Reference Comment
5.390385.1Manzo 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:


Reaction 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: John E. Bartmess

Note: Please consider using the reaction search for this species. This page allows searching of all reactions involving this species. A general reaction search form is also available. Future versions of this site may rely on reaction search pages in place of the enumerated reaction displays seen below.

Individual Reactions

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

By formula: C8H8NO2- + H+ = C8H9NO2

Quantity Value Units Method Reference Comment
Δr352.5 ± 2.1kcal/molG+TSTaft and Topsom, 1987gas phase; value altered from reference due to change in acidity scale
Quantity Value Units Method Reference Comment
Δr345.2 ± 2.0kcal/molIMRETaft and Topsom, 1987gas phase; value altered from reference due to change in acidity scale

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)211.3kcal/molN/AHunter and Lias, 1998HL
Quantity Value Units Method Reference Comment
Gas basicity203.9kcal/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
Δr352.5 ± 2.1kcal/molG+TSTaft and Topsom, 1987gas phase; value altered from reference due to change in acidity scale; B
Quantity Value Units Method Reference Comment
Δr345.2 ± 2.0kcal/molIMRETaft and Topsom, 1987gas phase; value altered from reference due to change in acidity scale; B

Mass spectrum (electron ionization)

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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: NIST Mass Spectrometry Data Center, William E. Wallace, director

Spectrum

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Mass spectrum
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Additional Data

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Owner NIST Mass Spectrometry Data Center
Collection (C) 2014 copyright by the U.S. Secretary of Commerce
on behalf of the United States of America. All rights reserved.
Origin NIST Mass Spectrometry Data Center, 2010
NIST MS number 374474

All mass spectra in this site (plus many more) are available from the NIST/EPA/NIH Mass Spectral Library. Please see the following for information about the library and its accompanying search program.


UV/Visible spectrum

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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: Victor Talrose, Alexander N. Yermakov, Alexy A. Usov, Antonina A. Goncharova, Axlexander N. Leskin, Natalia A. Messineva, Natalia V. Trusova, Margarita V. Efimkina

Spectrum

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UVVis spectrum
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Additional Data

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Source Lang (editor), 1973
Owner INEP CP RAS, NIST OSRD
Collection (C) 2007 copyright by the U.S. Secretary of Commerce
on behalf of the United States of America. All rights reserved.
Origin INSTITUTE OF ENERGY PROBLEMS OF CHEMICAL PHYSICS, RAS
Source reference RAS UV No. 19735
Instrument Unicam SP 800 B
Melting point 37.5

Gas Chromatography

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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: NIST Mass Spectrometry Data Center, William E. Wallace, director

Van Den Dool and Kratz RI, non-polar column, temperature ramp

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Column type Active phase I Reference Comment
CapillaryVF-5MS1529.Todua, 201130. m/0.25 mm/0.25 μm, He; Tstart: 60. C; Tend: 270. C

Normal alkane RI, non-polar column, isothermal

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Column type Active phase Temperature (C) I Reference Comment
CapillaryJXR180.1509.von Buchi, Lorini, et al., 1972 
CapillaryJXR200.1511.von Buchi, Lorini, et al., 1972 

Normal alkane RI, non-polar column, custom temperature program

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Column type Active phase I Reference Comment
CapillaryPolydimethyl siloxanes1546.Zenkevich and Chupalov, 1996Program: not specified

References

Go To: Top, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Mass spectrum (electron ionization), UV/Visible spectrum, Gas Chromatography, 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]

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]

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]

Lang (editor), 1973
Lang (editor), L., Absorption Spectra in the Ultraviolet and Visible Region, 1973, 18, 25. [all data]

Todua, 2011
Todua, N.G., Retention Data. NIST Mass Spectrometry Data Center., NIST Mass Spectrometry Data Center, 2011. [all data]

von Buchi, Lorini, et al., 1972
von Buchi, J.; Lorini, V.; Perlia, X., Gaschromatographische Untersuchung einiger homologer Reihen von Lokalanaesthetica, Pharm. Acta Helv., 1972, 47, 65, 377-393. [all data]

Zenkevich and Chupalov, 1996
Zenkevich, I.G.; Chupalov, A.A., New Possibilities of Chromato Mass Pectrometric Identification of Organic Compounds Using Increments of Gas Chromatographic Retention Indices of Molecular Structural Fragments, Zh. Org. Khim. (Rus.), 1996, 32, 5, 656-666. [all data]


Notes

Go To: Top, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Mass spectrum (electron ionization), UV/Visible spectrum, Gas Chromatography, References