3-Aminopyridine

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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
Δfsolid14.4 ± 0.2kcal/molCcbBickerton, Pilcher, et al., 1984 
Quantity Value Units Method Reference Comment
Δcsolid-689.6 ± 0.1kcal/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
Δsub19.3 ± 0.07kcal/molCSabbah and da Silva Eusébio, 1998AC
Δsub20.1 ± 0.33kcal/molCBickerton, Pilcher, et al., 1984ALS
Δsub20.1kcal/molN/ABickerton, Pilcher, et al., 1984DRB
Δsub20.1 ± 0.33kcal/molCBickerton, Pilcher, et al., 1984AC

Enthalpy of fusion

ΔfusH (kcal/mol) Temperature (K) Reference Comment
3.44335.5Sabbah 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 = 3-Aminopyridine

By formula: C5H5N2- + H+ = C5H6N2

Quantity Value Units Method Reference Comment
Δr360.6 ± 2.1kcal/molG+TSTaft and Bordwell, 1988gas phase; B
Quantity Value Units Method Reference Comment
Δr353.3 ± 2.0kcal/molIMRETaft and Bordwell, 1988gas phase; B

Lithium ion (1+) + 3-Aminopyridine = (Lithium ion (1+) • 3-Aminopyridine)

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

Quantity Value Units Method Reference Comment
Δr48.2 ± 2.5kcal/molCIDTRodgers, 2001RCD

Sodium ion (1+) + 3-Aminopyridine = (Sodium ion (1+) • 3-Aminopyridine)

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

Quantity Value Units Method Reference Comment
Δr32.5 ± 0.9kcal/molCIDTRodgers, 2001RCD

Potassium ion (1+) + 3-Aminopyridine = (Potassium ion (1+) • 3-Aminopyridine)

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

Quantity Value Units Method Reference Comment
Δr24.2 ± 0.8kcal/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

Quantity Value Units Method Reference Comment
Proton affinity (review)228.1kcal/molN/AHunter and Lias, 1998HL
Quantity Value Units Method Reference Comment
Gas basicity220.5kcal/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
Δr360.6 ± 2.1kcal/molG+TSTaft and Bordwell, 1988gas phase; B
Quantity Value Units Method Reference Comment
Δr353.3 ± 2.0kcal/molIMRETaft and Bordwell, 1988gas phase; B

IR 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: 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 Copyright (C) 1987 by the 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 SOUTHERN RESEARCH INSTITUTE
Source reference COBLENTZ NO. 6850
Date 1967/04/13
Name(s) 3-pyridinylamine
3-pyridinamine
State SOLID (1 mg / 650 mg KBr DISC)
Instrument PERKIN-ELMER 521 (GRATING)
Instrument parameters FILTERS AT 3150, 2500, 2000, 1150, 700, 410. GRATING CHANGES: 2000, 630
Resolution 2
Data processing (ADJUSTED addcm-112-12-12)

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


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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Due to licensing restrictions, this spectrum cannot be downloaded.

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-2299
NIST MS number 230345

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, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics 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, 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 Grammaticakis, 1959
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. 12952
Instrument n.i.g.
Melting point 64.5
Boiling point 252

Gas Chromatography

Go To: Top, 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: 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-40M150.2156.Terenina, Zhuravieva, et al., 199750. m/0.3 mm/0.4 μm, He
PackedPEG-2000179.2143.Anderson, Jurel, et al., 1973He, Celite 545 (44-60 mesh); Column length: 3. m
PackedPEG-2000180.2142.Anderson, Jurel, et al., 1973He, Celite 545 (44-60 mesh); Column length: 3. m
PackedPEG-2000200.2122.Anderson, Jurel, et al., 1973He, Celite 545 (44-60 mesh); Column length: 3. m
PackedPEG-2000200.2125.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-51105.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
CapillaryCAM2111.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, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics 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]

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]

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]

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

Grammaticakis, 1959
Grammaticakis, P., Bull. soc. chim. France, 1959, Series 5, 480. [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, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, Gas Chromatography, References