3-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
Δfgas144.2 ± 1.6kJ/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
Δfsolid60.2 ± 0.8kJ/molCcbBickerton, Pilcher, et al., 1984 
Quantity Value Units Method Reference Comment
Δcsolid-2885.2 ± 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
Tboil521.2KN/AAldrich Chemical Company Inc., 1990BS
Tboil525.2KN/AWeast and Grasselli, 1989BS
Tboil519. to 521.KN/AFrinton Laboratories Inc., 1986BS
Tboil523. to 525.KN/ABuckingham and Donaghy, 1982BS
Quantity Value Units Method Reference Comment
Tfus337.KN/ABuckingham and Donaghy, 1982BS
Tfus337.15KN/AWaclawek and Hurwic, 1967Uncertainty assigned by TRC = 1.5 K; TRC
Tfus337.65KN/ACumper, Ginman, et al., 1963Uncertainty assigned by TRC = 0.2 K; TRC
Quantity Value Units Method Reference Comment
Δsub80.7 ± 0.3kJ/molCSabbah and da Silva Eusébio, 1998AC
Δsub84.0 ± 1.4kJ/molCBickerton, Pilcher, et al., 1984ALS
Δsub84.0kJ/molN/ABickerton, Pilcher, et al., 1984DRB
Δsub84.0 ± 1.4kJ/molCBickerton, Pilcher, et al., 1984AC

Enthalpy of fusion

ΔfusH (kJ/mol) Temperature (K) Reference Comment
14.4335.5Sabbah 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:


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

Quantity Value Units Method Reference Comment
Proton affinity (review)954.4kJ/molN/AHunter and Lias, 1998HL
Quantity Value Units Method Reference Comment
Gas basicity922.6kJ/molN/AHunter and Lias, 1998HL

Ionization energy determinations

IE (eV) Method Reference Comment
8.7 ± 0.1EIStefanovic and Grutzmacher, 1974LLK
9.03 ± 0.05EIGronneberg and Undheim, 1973LLK
9.0CTSDaisey and Sonnessa, 1972LLK
8.44PEKobayashi and Nagakura, 1974Vertical value; LLK

De-protonation reactions

C5H5N2- + Hydrogen cation = 3-Aminopyridine

By formula: C5H5N2- + H+ = C5H6N2

Quantity Value Units Method Reference Comment
Δr1509. ± 8.8kJ/molG+TSTaft and Bordwell, 1988gas phase; B
Quantity Value Units Method Reference Comment
Δr1478. ± 8.4kJ/molIMRETaft and Bordwell, 1988gas phase; B

References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, 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]

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]

Frinton Laboratories Inc., 1986
Frinton Laboratories Inc., Catalog Number 11, Frinton Laboratories Inc., Vineland, NJ, 1986, 99. [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]

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]

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


Notes

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