Home Symbol which looks like a small house Up Solid circle with an upward pointer in it

4-Aminopyridine

Data at NIST subscription sites:

NIST subscription sites provide data under the NIST Standard Reference Data Program, but require an annual fee to access. The purpose of the fee is to recover costs associated with the development of data collections included in such sites. Your institution may already be a subscriber. Follow the links above to find out more about the data in these sites and their terms of usage.


Gas phase thermochemistry data

Go To: Top, 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: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Quantity Value Units Method Reference Comment
Deltafgas31.05 ± 0.33kcal/molCcbBickerton, Pilcher, et al., 1984 

Condensed phase thermochemistry data

Go To: Top, Gas 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: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Quantity Value Units Method Reference Comment
Deltafsolid10. ± 0.2kcal/molCcbBickerton, Pilcher, et al., 1984 
Quantity Value Units Method Reference Comment
Deltacsolid-685.2 ± 0.1kcal/molCcbBickerton, Pilcher, et al., 1984 

Phase change data

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry 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 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
Deltasub20.8 ± 0.1kcal/molCSabbah and da Silva Eusébio, 1998AC
Deltasub21.1 ± 0.26kcal/molCBickerton, Pilcher, et al., 1984ALS
Deltasub21.1kcal/molN/ABickerton, Pilcher, et al., 1984DRB
Deltasub21.1 ± 0.26kcal/molCBickerton, Pilcher, et al., 1984AC

Reduced pressure boiling point

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

Enthalpy of fusion

DeltafusH (kcal/mol) Temperature (K) Method Reference Comment
4.797429.9DSCDonnelly, 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

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change 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 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
Deltar357.0 ± 2.2kcal/molG+TSTaft and Bordwell, 1988gas phase; B
Quantity Value Units Method Reference Comment
Deltar349.8 ± 2.0kcal/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
Deltar51.8 ± 5.0kcal/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
Deltar35.0 ± 1.1kcal/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
Deltar26.0 ± 0.8kcal/molCIDTRodgers, 2001RCD

Gas phase ion energetics data

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry 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 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)234.2kcal/molN/AHunter and Lias, 1998HL
Quantity Value Units Method Reference Comment
Gas basicity226.5kcal/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
Deltar357.0 ± 2.2kcal/molG+TSTaft and Bordwell, 1988gas phase; B
Quantity Value Units Method Reference Comment
Deltar349.8 ± 2.0kcal/molIMRETaft and Bordwell, 1988gas phase; B

Ion clustering data

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics 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: 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
Deltar26.0 ± 0.8kcal/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
Deltar51.8 ± 5.0kcal/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
Deltar35.0 ± 1.1kcal/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, 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

Notice: This spectrum may be better viewed with a Javascript and HTML 5 enabled browser.

IR spectrum
For Zoom
1.) Enter the desired X axis range (e.g., 100, 200)
2.) Check here for automatic Y scaling
3.) Press here to zoom

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

View scan of original (hardcopy) spectrum.

View image of digitized spectrum (can be printed in landscape orientation).

View spectrum image in SVG format.

Download spectrum in JCAMP-DX format.

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, 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

Notice: This spectrum may be better viewed with a Javascript and HTML 5 enabled browser.

Mass spectrum
For Zoom
1.) Enter the desired X axis range (e.g., 100, 200)
2.) Check here for automatic Y scaling
3.) Press here to zoom

Additional Data

View image of digitized spectrum (can be printed in landscape orientation).

View spectrum image in SVG format.

Download spectrum in JCAMP-DX format.

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

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

Spectrum

Notice: This spectrum may be better viewed with a Javascript and HTML 5 enabled browser.

UVVis spectrum
For Zoom
1.) Enter the desired X axis range (e.g., 100, 200)
2.) Check here for automatic Y scaling
3.) Press here to zoom

Additional Data

View image of digitized spectrum (can be printed in landscape orientation).

View spectrum image in SVG format.

Download spectrum in JCAMP-DX format.

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

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, 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]


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, References