Benzoic acid, 4-amino-, methyl ester

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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

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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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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

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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, Reaction thermochemistry data, Gas phase ion energetics data, Mass spectrum (electron ionization), Gas Chromatography, Notes

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

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]

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

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