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4-Aminopyridine

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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
Deltafgas129.9 ± 1.4kJ/molCcbBickerton, Pilcher, et al., 1984 

Condensed 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
Deltafsolid41.8 ± 0.8kJ/molCcbBickerton, Pilcher, et al., 1984 
Quantity Value Units Method Reference Comment
Deltacsolid-2866.8 ± 0.5kJ/molCcbBickerton, Pilcher, et al., 1984 

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:
BS - Robert L. Brown and Stephen E. Stein
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny, director
AC - William E. Acree, Jr., James S. Chickos
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DRB - Donald R. Burgess, Jr.

Quantity Value Units Method Reference Comment
Tboil546.2KN/AWeast and Grasselli, 1989BS
Quantity Value Units Method Reference Comment
Tfus431.98KN/ADonnelly, Drewes, et al., 1990Uncertainty assigned by TRC = 0.2 K; TRC
Tfus431.KN/ABuckingham and Donaghy, 1982BS
Tfus432.15KN/ACumper, Ginman, et al., 1963Uncertainty assigned by TRC = 0.5 K; TRC
Tfus432.65KN/ALeis and Curran, 1945Uncertainty assigned by TRC = 1. K; TRC
Quantity Value Units Method Reference Comment
Deltasub87.1 ± 0.4kJ/molCSabbah and da Silva Eusébio, 1998AC
Deltasub88.1 ± 1.1kJ/molCBickerton, Pilcher, et al., 1984ALS
Deltasub88.1kJ/molN/ABickerton, Pilcher, et al., 1984DRB
Deltasub88.1 ± 1.1kJ/molCBickerton, Pilcher, et al., 1984AC

Reduced pressure boiling point

Tboil (K) Pressure (bar) Reference Comment
453.0.016Buckingham and Donaghy, 1982BS

Enthalpy of fusion

DeltafusH (kJ/mol) Temperature (K) Method Reference Comment
20.07429.9DSCDonnelly, Drewes, et al., 1990, 2AC

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 as indicated in comments:
B - John E. Bartmess
RCD - Robert C. Dunbar

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

C5H5N2- + Hydrogen cation = 4-Aminopyridine

By formula: C5H5N2- + H+ = C5H6N2

Quantity Value Units Method Reference Comment
Deltar1494. ± 9.2kJ/molG+TSTaft and Bordwell, 1988gas phase; B
Quantity Value Units Method Reference Comment
Deltar1464. ± 8.4kJ/molIMRETaft and Bordwell, 1988gas phase; B

Lithium ion (1+) + 4-Aminopyridine = (Lithium ion (1+) bullet 4-Aminopyridine)

By formula: Li+ + C5H6N2 = (Li+ bullet C5H6N2)

Quantity Value Units Method Reference Comment
Deltar217. ± 21.kJ/molCIDTRodgers, 2001RCD

Sodium ion (1+) + 4-Aminopyridine = (Sodium ion (1+) bullet 4-Aminopyridine)

By formula: Na+ + C5H6N2 = (Na+ bullet C5H6N2)

Quantity Value Units Method Reference Comment
Deltar146. ± 4.6kJ/molCIDTRodgers, 2001RCD

Potassium ion (1+) + 4-Aminopyridine = (Potassium ion (1+) bullet 4-Aminopyridine)

By formula: K+ + C5H6N2 = (K+ bullet C5H6N2)

Quantity Value Units Method Reference Comment
Deltar109. ± 3.kJ/molCIDTRodgers, 2001RCD

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)979.7kJ/molN/AHunter and Lias, 1998HL
Quantity Value Units Method Reference Comment
Gas basicity947.8kJ/molN/AHunter and Lias, 1998HL

Ionization energy determinations

IE (eV) Method Reference Comment
8.8 ± 0.1EIStefanovic and Grutzmacher, 1974LLK
9.27 ± 0.05EIGronneberg and Undheim, 1973LLK
8.4CTSDaisey and Sonnessa, 1972LLK
8.97 ± 0.05EIBasila and Clancy, 1963RDSH
8.77PERamsey and Walker, 1974Vertical value; LLK
8.76PEKobayashi and Nagakura, 1974Vertical value; LLK

De-protonation reactions

C5H5N2- + Hydrogen cation = 4-Aminopyridine

By formula: C5H5N2- + H+ = C5H6N2

Quantity Value Units Method Reference Comment
Deltar1494. ± 9.2kJ/molG+TSTaft and Bordwell, 1988gas phase; B
Quantity Value Units Method Reference Comment
Deltar1464. ± 8.4kJ/molIMRETaft and Bordwell, 1988gas phase; B

Ion clustering 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: Robert C. Dunbar

Note: Please consider using the reaction search for this species. This page allows searching of all reactions involving this species. Searches may be limited to ion clustering reactions. A general reaction search form is also available.

Clustering reactions

Potassium ion (1+) + 4-Aminopyridine = (Potassium ion (1+) bullet 4-Aminopyridine)

By formula: K+ + C5H6N2 = (K+ bullet C5H6N2)

Quantity Value Units Method Reference Comment
Deltar109. ± 3.kJ/molCIDTRodgers, 2001 

Lithium ion (1+) + 4-Aminopyridine = (Lithium ion (1+) bullet 4-Aminopyridine)

By formula: Li+ + C5H6N2 = (Li+ bullet C5H6N2)

Quantity Value Units Method Reference Comment
Deltar217. ± 21.kJ/molCIDTRodgers, 2001 

Sodium ion (1+) + 4-Aminopyridine = (Sodium ion (1+) bullet 4-Aminopyridine)

By formula: Na+ + C5H6N2 = (Na+ bullet C5H6N2)

Quantity Value Units Method Reference Comment
Deltar146. ± 4.6kJ/molCIDTRodgers, 2001 

IR Spectrum

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

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

Data compiled by: Coblentz Society, Inc.

Condensed Phase Spectrum

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IR spectrum
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Notice: Except where noted, spectra from this collection were measured on dispersive instruments, often in carefully selected solvents, and hence may differ in detail from measurements on FTIR instruments or in other chemical environments. More information on the manner in which spectra in this collection were collected can be found here.

Notice: Concentration information is not available for this spectrum and, therefore, molar absorptivity values cannot be derived.

Additional Data

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Owner COBLENTZ SOCIETY
Collection (C) 2018 copyright by the U.S. Secretary of Commerce
on behalf of the United States of America. All rights reserved.
Origin DOW CHEMICAL COMPANY
Source reference COBLENTZ NO. 10653
Date 1963/07/26
Name(s) 4-pyridinylamine
4-pyridinamine
State SOLID (SPLIT MULL, FLUOROLUBE FOR 3800-1330 AND NUJOL FOR 1330-450 CM -1)
Instrument DOW KBr FOREPRISM-GRATING
Instrument parameters BLAZED AT 3.5, 12.0, 20.0 MICRON, CHANGED AT 5.0, 7.5, 14.9 MICRON
Resolution 4
Sampling procedure TRANSMISSION
Data processing DIGITIZED BY NIST FROM HARD COPY (FROM TWO SEGMENTS)
Melting point 158 C

This IR spectrum is from the Coblentz Society's evaluated infrared reference spectra collection.


Mass spectrum (electron ionization)

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering data, IR Spectrum, UV/Visible spectrum, Gas Chromatography, References, Notes

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 Japan AIST/NIMC Database- Spectrum MS-NW-1397
NIST MS number 230175

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 Blizniukov and Shinkorenko, 1958
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. 12955
Instrument n.i.g.
Melting point 158.5

Gas Chromatography

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, References, Notes

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

Kovats' RI, non-polar column, isothermal

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Column type Active phase Temperature (C) I Reference Comment
CapillaryOV-101150.1170.Terenina, Zhuravieva, et al., 199750. m/0.3 mm/0.4 «mu»m, He

Kovats' RI, polar column, isothermal

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Column type Active phase Temperature (C) I Reference Comment
CapillaryPEG-40M150.2278.Terenina, Zhuravieva, et al., 199750. m/0.3 mm/0.4 «mu»m, He
PackedPEG-2000179.2325.Anderson, Jurel, et al., 1973He, Celite 545 (44-60 mesh); Column length: 3. m
PackedPEG-2000180.2324.Anderson, Jurel, et al., 1973He, Celite 545 (44-60 mesh); Column length: 3. m
PackedPEG-2000200.2298.Anderson, Jurel, et al., 1973He, Celite 545 (44-60 mesh); Column length: 3. m
PackedPEG-2000200.2300.Anderson, Jurel, et al., 1973He, Celite 545 (44-60 mesh); Column length: 3. m

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

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Column type Active phase I Reference Comment
CapillaryDB-51158.Premecz and Ford, 1987He, 60. C @ 10. min, 10. K/min, 280. C @ 3. min; Column length: 30. m; Column diameter: 0.32 mm

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

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Column type Active phase I Reference Comment
CapillaryCAM2287.Premecz and Ford, 1987He, 60. C @ 5. min, 5. K/min, 240. C @ 21. min; Column length: 15. m; Column diameter: 0.24 mm

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

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Column type Active phase I Reference Comment
CapillaryNonpolar1158.Staples and Zeiger, 2008Program: not specified

References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering data, IR Spectrum, 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.

Bickerton, Pilcher, et al., 1984
Bickerton, J.; Pilcher, G.; Al-Takhin, G., Enthalpies of combustion of the three aminopyridines and the three cyanopyridines, J. Chem. Thermodyn., 1984, 16, 373-378. [all data]

Weast and Grasselli, 1989
CRC Handbook of Data on Organic Compounds, 2nd Editon, Weast,R.C and Grasselli, J.G., ed(s)., CRC Press, Inc., Boca Raton, FL, 1989, 1. [all data]

Donnelly, Drewes, et al., 1990
Donnelly, J.R.; Drewes, L.A.; Johnson, R.L.; Munslow, W.D.; Knapp, K.K.; Sovocool, G.W., Purity and heat of fusion data for environmental standards as determined by differential scanning calorimetry, Thermochim. Acta, 1990, 167, 2, 155, https://doi.org/10.1016/0040-6031(90)80476-F . [all data]

Buckingham and Donaghy, 1982
Buckingham, J.; Donaghy, S.M., Dictionary of Organic Compounds: Fifth Edition, Chapman and Hall, New York, 1982, 1. [all data]

Cumper, Ginman, et al., 1963
Cumper, C.W.N.; Ginman, R.F.A.; Redford, D.G.; Vogel, A.I., Physical Properties and Chemical Constitution. Part XXXVIII. The Electric Dipole Moments of Aminopyridines and Aminoquinolines., J. Chem. Soc., 1963, 1963, 1731. [all data]

Leis and Curran, 1945
Leis, D.G.; Curran, B.C., Electric moments of some gamma-substituted pyridines, J. Am. Chem. Soc., 1945, 67, 79. [all data]

Sabbah and da Silva Eusébio, 1998
Sabbah, Raphaël; da Silva Eusébio, Maria Ermelinda, Energétique des liaisons inter- et intramoléculaires dans les trois isomères de l'aminopyridine, Revue canadienne de chimie, 1998, 76, 1, 18-24, https://doi.org/10.1139/cjc-76-1-18 . [all data]

Donnelly, Drewes, et al., 1990, 2
Donnelly, J.R.; Drewes, L.A.; Johnson, R.L.; Munslow, W.D.; Knapp, K.K.; Sovocool, G.W., Purity and heat of fusion data for environmental standards as determined by differential scanning calorimetry, Thermochimica Acta, 1990, 167, 2, 155-187, https://doi.org/10.1016/0040-6031(90)80476-F . [all data]

Taft and Bordwell, 1988
Taft, R.W.; Bordwell, F.G., Structural and Solvent Effects Evaluated from Acidities Measured in Dimethyl Sulfoxide and in the Gas Phase, Acc. Chem. Res., 1988, 21, 12, 463, https://doi.org/10.1021/ar00156a005 . [all data]

Rodgers, 2001
Rodgers, M.T., Substituent Effects in the Binding of Alkali Metal Ions to Pyridines, Studied by Threshold Collision-Induced Dissociation and ab Initio Theory: The Aminopyridines, J. Phys. Chem. A, 2001, 105, 35, 8145, https://doi.org/10.1021/jp011555z . [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]

Stefanovic and Grutzmacher, 1974
Stefanovic, D.; Grutzmacher, H.F., The ionisation potential of some substituted pyridines, Org. Mass Spectrom., 1974, 9, 1052. [all data]

Gronneberg and Undheim, 1973
Gronneberg, T.; Undheim, K., Mass spectrometry of onium compounds - XV. ionization potentials of amino pyridines, Tetrahedron Lett., 1973, 3193. [all data]

Daisey and Sonnessa, 1972
Daisey, J.M.; Sonnessa, A.J., A study of the thermodynamic and spectral properties of molecular complexes of iodine with several aminopyridines, J. Phys. Chem., 1972, 76, 1895. [all data]

Basila and Clancy, 1963
Basila, M.R.; Clancy, D.J., The ionization potentials of monosubstituted pyridines by electron impact, J. Phys. Chem., 1963, 67, 1551. [all data]

Ramsey and Walker, 1974
Ramsey, B.G.; Walker, F.A., A linear relationship between substituted pyridine lone pair vertical ionization potentials and pKa, J. Am. Chem. Soc., 1974, 96, 3314. [all data]

Kobayashi and Nagakura, 1974
Kobayashi, T.; Nagakura, S., Photoelectron spectra of aminopyridines and cyanopyridines, J. Electron Spectrosc. Relat. Phenom., 1974, 4, 207. [all data]

Blizniukov and Shinkorenko, 1958
Blizniukov, V.I.; Shinkorenko, N.T., Zhur. Obschei Khim., 1958, 28, 1241. [all data]

Terenina, Zhuravieva, et al., 1997
Terenina, M.B.; Zhuravieva, I.L.; Golovnya, R.V., Peculiar features of sorption of positional isomers of formyl-, acetyl-, and aminopyridines in capillary gas-liquid chromatography, Russ. Chem. Bull. (Engl. Transl.), 1997, 46, 1, 86-89, https://doi.org/10.1007/BF02495353 . [all data]

Anderson, Jurel, et al., 1973
Anderson, A.; Jurel, S.; Shymanska, M.; Golender, L., Gas-liquid chromatography of some aliphatic and heterocyclic mono- and pollyfunctional amines. VII. Retention indices of amines in some polar and unpolar stationary phases, Latv. PSR Zinat. Akad. Vestis Kim. Ser., 1973, 1, 51-63. [all data]

Premecz and Ford, 1987
Premecz, J.E.; Ford, M.E., Gas chromatographic separation of substituted pyridines, J. Chromatogr., 1987, 388, 23-35, https://doi.org/10.1016/S0021-9673(01)94463-2 . [all data]

Staples and Zeiger, 2008
Staples, E.; Zeiger, K., On-Site Measurements of VOCs and Odors from Metal Casting Operations Using an Ultra-Fast Gas Chromatograph, 2008, retrieved from http://www.estcal.com/TechPapers/Industrial/FoundryOdors.doc. [all data]


Notes

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