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2-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
Deltafgas118.1 ± 1.1kJ/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
Deltafsolid39.4 ± 0.8kJ/molCcbBickerton, Pilcher, et al., 1984 
Quantity Value Units Method Reference Comment
Deltacsolid-2864.4 ± 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
Tboil480.2KN/AAldrich Chemical Company Inc., 1990BS
Tboil477.KN/ABuckingham and Donaghy, 1982BS
Quantity Value Units Method Reference Comment
Tfus330.6KN/ABuckingham and Donaghy, 1982BS
Tfus329.15KN/AWaclawek and Hurwic, 1967Uncertainty assigned by TRC = 1.5 K; TRC
Tfus331.65KN/ACumper, Ginman, et al., 1963Uncertainty assigned by TRC = 0.2 K; TRC
Quantity Value Units Method Reference Comment
Deltasub76.5 ± 0.4kJ/molCSabbah and da Silva Eusébio, 1998AC
Deltasub78.7 ± 0.8kJ/molCBickerton, Pilcher, et al., 1984ALS
Deltasub78.7kJ/molN/ABickerton, Pilcher, et al., 1984DRB
Deltasub78.7 ± 0.8kJ/molCBickerton, Pilcher, et al., 1984AC

Reduced pressure boiling point

Tboil (K) Pressure (bar) Reference Comment
377. - 379.0.027Buckingham and Donaghy, 1982BS

Enthalpy of fusion

DeltafusH (kJ/mol) Temperature (K) Reference Comment
15.3331.5Sabbah and da Silva Eusébio, 1998AC

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 = 2-Aminopyridine

By formula: C5H5N2- + H+ = C5H6N2

Quantity Value Units Method Reference Comment
Deltar1519. ± 10.kJ/molTDEqMeot-ner and Kafafi, 1988gas phase; anchored to 88MEO scale, not the "87 acidity scale". The Kiefer, Zhang, et al., 1997 BDE is for ortho.; B
Deltar1518. ± 8.8kJ/molG+TSTaft and Bordwell, 1988gas phase; B
Quantity Value Units Method Reference Comment
Deltar1489. ± 8.4kJ/molTDEqMeot-ner and Kafafi, 1988gas phase; anchored to 88MEO scale, not the "87 acidity scale". The Kiefer, Zhang, et al., 1997 BDE is for ortho.; B
Deltar1488. ± 8.4kJ/molIMRETaft and Bordwell, 1988gas phase; B

Lithium ion (1+) + 2-Aminopyridine = (Lithium ion (1+) bullet 2-Aminopyridine)

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

Quantity Value Units Method Reference Comment
Deltar238. ± 21.kJ/molCIDTRodgers, 2001RCD

Sodium ion (1+) + 2-Aminopyridine = (Sodium ion (1+) bullet 2-Aminopyridine)

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

Quantity Value Units Method Reference Comment
Deltar146. ± 5.9kJ/molCIDTRodgers, 2001RCD

Potassium ion (1+) + 2-Aminopyridine = (Potassium ion (1+) bullet 2-Aminopyridine)

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

Quantity Value Units Method Reference Comment
Deltar103. ± 4.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
LL - Sharon G. Lias and Joel F. Liebman
LBLHLM - Sharon G. Lias, John E. Bartmess, Joel F. Liebman, John L. Holmes, Rhoda D. Levin, and W. Gary Mallard
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi

Quantity Value Units Method Reference Comment
Proton affinity (review)947.2kJ/molN/AHunter and Lias, 1998HL
Quantity Value Units Method Reference Comment
Gas basicity915.3kJ/molN/AHunter and Lias, 1998HL

Ionization energy determinations

IE (eV) Method Reference Comment
8.099 ± 0.003PEKim, Thantu, et al., 1992LL
8.0PEGuimon, Khayar, et al., 1982LBLHLM
9.3CTSDaisey and Sonnessa, 1972LLK
8.4PEGuimon, Khayar, et al., 1982Vertical value; LBLHLM
8.5 ± 0.1EIStefanovic and Grutzmacher, 1974Vertical value; LLK
8.34PEKobayashi and Nagakura, 1974Vertical value; LLK
8.85 ± 0.05EIGronneberg and Undheim, 1973Vertical value; LLK

De-protonation reactions

C5H5N2- + Hydrogen cation = 2-Aminopyridine

By formula: C5H5N2- + H+ = C5H6N2

Quantity Value Units Method Reference Comment
Deltar1519. ± 10.kJ/molTDEqMeot-ner and Kafafi, 1988gas phase; anchored to 88MEO scale, not the "87 acidity scale". The Kiefer, Zhang, et al., 1997 BDE is for ortho.; B
Deltar1518. ± 8.8kJ/molG+TSTaft and Bordwell, 1988gas phase; B
Quantity Value Units Method Reference Comment
Deltar1489. ± 8.4kJ/molTDEqMeot-ner and Kafafi, 1988gas phase; anchored to 88MEO scale, not the "87 acidity scale". The Kiefer, Zhang, et al., 1997 BDE is for ortho.; B
Deltar1488. ± 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+) + 2-Aminopyridine = (Potassium ion (1+) bullet 2-Aminopyridine)

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

Quantity Value Units Method Reference Comment
Deltar103. ± 4.kJ/molCIDTRodgers, 2001 

Lithium ion (1+) + 2-Aminopyridine = (Lithium ion (1+) bullet 2-Aminopyridine)

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

Quantity Value Units Method Reference Comment
Deltar238. ± 21.kJ/molCIDTRodgers, 2001 

Sodium ion (1+) + 2-Aminopyridine = (Sodium ion (1+) bullet 2-Aminopyridine)

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

Quantity Value Units Method Reference Comment
Deltar146. ± 5.9kJ/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 compiled by: Coblentz Society, Inc.

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


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, 1998.
NIST MS number 290677

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), 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: Victor Talrose, Eugeny B. Stern, Antonina A. Goncharova, 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 Steck and Ewing, 1948
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. 43
Instrument n.i.g.
Melting point 57.5
Boiling point 105(20)

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, polar column, isothermal

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Column type Active phase Temperature (C) I Reference Comment
CapillaryPEG-40M150.1892.Terenina, Zhuravieva, et al., 199750. m/0.3 mm/0.4 «mu»m, He
PackedPEG-2000179.1915.Anderson, Jurel, et al., 1973He, Celite 545 (44-60 mesh); Column length: 3. m
PackedPEG-2000180.1896.Anderson, Jurel, et al., 1973He, Celite 545 (44-60 mesh); Column length: 3. m
PackedPEG-2000200.1889.Anderson, Jurel, et al., 1973He, Celite 545 (44-60 mesh); Column length: 3. m
PackedPEG-2000200.1906.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-51002.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
CapillaryCAM1873.Premecz and Ford, 1987He, 60. C @ 5. min, 5. K/min, 240. C @ 21. min; Column length: 15. m; Column diameter: 0.24 mm

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]

Aldrich Chemical Company Inc., 1990
Aldrich Chemical Company Inc., Catalog Handbook of Fine Chemicals, Aldrich Chemical Company, Inc., Milwaukee WI, 1990, 1. [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]

Waclawek and Hurwic, 1967
Waclawek, Z.; Hurwic, J., Dipole moment and spectroscopic studies of the 1,3,5-trinitrobenzene complexes with some pyridine derivatives in nonpolar solvents, Rocz. Chem., 1967, 41, 1993. [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]

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]

Meot-ner and Kafafi, 1988
Meot-ner, M.; Kafafi, S.A., Carbon Acidities of Aromatic Compounds, J. Am. Chem. Soc., 1988, 110, 19, 6297, https://doi.org/10.1021/ja00227a003 . [all data]

Kiefer, Zhang, et al., 1997
Kiefer, J.H.; Zhang, Q.; Kern, R.D.; Yao, J.; Jursic, B., Pyrolysis of Aromatic Azines: Pyrazine, Pyrimidine, and Pyridine, J. Phys. Chem. A, 1997, 101, 38, 7061, https://doi.org/10.1021/jp970211z . [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]

Kim, Thantu, et al., 1992
Kim, B.; Thantu, N.; Weber, P.M., High resolution photoelectron spectroscopy: The vibrational spectrum of the 2-aminopyridine cation, J. Chem. Phys., 1992, 97, 5384. [all data]

Guimon, Khayar, et al., 1982
Guimon, C.; Khayar, S.; Pfister-Guillouzo, G.; Claramunt, R.M.; Elguero, J., A direct photoelectron spectroscopy study of the 1-azidopyridine pyrolysis, Spectrosc. Lett., 1982, 15, 435. [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]

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

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]

Steck and Ewing, 1948
Steck, E.A.; Ewing, G.W., Absorption spectra of heterocyclic compounds. II. Amino-derivatives of pyridine, quinoline and isoquinoline, J. Am. Chem. Soc., 1948, 70, 3397-3406. [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]


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