4-Aminopyridine

• Formula: C₅H₆N₂
• Molecular weight: 94.1145
• IUPAC Standard InChI: InChI=1S/C5H6N2/c6-5-1-3-7-4-2-5/h1-4H,(H2,6,7) Copy

  
• IUPAC Standard InChIKey: NUKYPUAOHBNCPY-UHFFFAOYSA-N Copy
• CAS Registry Number: 504-24-5
• Chemical structure:
  This structure is also available as a 2d Mol file or as a computed 3d SD file
  The 3d structure may be viewed using Java or Javascript.
• Other names: Fampridine; 4-Pyridinamine; Pyridine, 4-amino-; γ-Aminopyridine; p-Aminopyridine; Phillips 1861; VMI 10-3; 4-Pyridylamine; Amino-4 pyridine; Avitrol; Avitrol 200; Compound 1861; Pimadin (free base); Prc 1237; 4-AP; Rcra waste number P008; NSC 15041; Frampridine
• Permanent link for this species. Use this link for bookmarking this species for future reference.
• Information on this page:
  • Gas phase thermochemistry data
  • Reaction thermochemistry data
  • Gas phase ion energetics data
  • Ion clustering data
  • Gas Chromatography
  • References
  • Notes
• Other data available:
  • Condensed phase thermochemistry data
  • Phase change data
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • UV/Visible spectrum
• Options:
  • Switch to SI units

Data at NIST subscription sites:

• NIST / TRC Web Thermo Tables, professional edition (thermophysical and thermochemical data)

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, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering data, 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: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Reaction thermochemistry data

Go To: Top, Gas phase thermochemistry data, Gas phase ion energetics data, Ion clustering data, 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 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^- +  =

By formula: C₅H₅N₂^- + H⁺ = C₅H₆N₂

 +  = ( • )

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

 +  = ( • )

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

 +  = ( • )

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

Gas phase ion energetics data

Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry data, Ion clustering data, 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 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

Ionization energy determinations

De-protonation reactions

C₅H₅N₂^- +  =

By formula: C₅H₅N₂^- + H⁺ = C₅H₆N₂

Ion clustering data

Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, 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: 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

 +  = ( • )

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

 +  = ( • )

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

 +  = ( • )

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

Gas Chromatography

Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering data, 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

View large format table.

Kovats' RI, polar column, isothermal

View large format table.

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

View large format table.

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

View large format table.

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

View large format table.

References

Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering data, 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]

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 pK_a, 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]

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, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering data, Gas Chromatography, References

• Symbols used in this document:
  

  ΔfH°gas	Enthalpy of formation of gas at standard conditions
  ΔrG°	Free energy of reaction at standard conditions
  ΔrH°	Enthalpy of reaction at standard conditions

• Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
• The National Institute of Standards and Technology (NIST) uses its best efforts to deliver a high quality copy of the Database and to verify that the data contained therein have been selected on the basis of sound scientific judgment. However, NIST makes no warranties to that effect, and NIST shall not be liable for any damage that may result from errors or omissions in the Database.
• Customer support for NIST Standard Reference Data products.