3-Aminopyridine
- Formula: C5H6N2
- Molecular weight: 94.1145
- IUPAC Standard InChIKey: CUYKNJBYIJFRCU-UHFFFAOYSA-N
- CAS Registry Number: 462-08-8
- 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: 3-Pyridinamine; Pyridine, 3-amino-; β-Aminopyridine; 3-Pyridylamine; Amino-3 pyridine; m-Aminopyridine; UN 2671
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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, 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 |
---|---|---|---|---|---|
ΔfH°gas | 144.2 ± 1.6 | kJ/mol | Ccb | Bickerton, 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 |
---|---|---|---|---|---|
ΔfH°solid | 60.2 ± 0.8 | kJ/mol | Ccb | Bickerton, Pilcher, et al., 1984 | |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°solid | -2885.2 ± 0.5 | kJ/mol | Ccb | Bickerton, 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 |
---|---|---|---|---|---|
Tboil | 521.2 | K | N/A | Aldrich Chemical Company Inc., 1990 | BS |
Tboil | 525.2 | K | N/A | Weast and Grasselli, 1989 | BS |
Tboil | 519. to 521. | K | N/A | Frinton Laboratories Inc., 1986 | BS |
Tboil | 523. to 525. | K | N/A | Buckingham and Donaghy, 1982 | BS |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 337. | K | N/A | Buckingham and Donaghy, 1982 | BS |
Tfus | 337.15 | K | N/A | Waclawek and Hurwic, 1967 | Uncertainty assigned by TRC = 1.5 K; TRC |
Tfus | 337.65 | K | N/A | Cumper, Ginman, et al., 1963 | Uncertainty assigned by TRC = 0.2 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔsubH° | 80.7 ± 0.3 | kJ/mol | C | Sabbah and da Silva Eusébio, 1998 | AC |
ΔsubH° | 84.0 ± 1.4 | kJ/mol | C | Bickerton, Pilcher, et al., 1984 | ALS |
ΔsubH° | 84.0 | kJ/mol | N/A | Bickerton, Pilcher, et al., 1984 | DRB |
ΔsubH° | 84.0 ± 1.4 | kJ/mol | C | Bickerton, Pilcher, et al., 1984 | AC |
Enthalpy of fusion
ΔfusH (kJ/mol) | Temperature (K) | Reference | Comment |
---|---|---|---|
14.4 | 335.5 | Sabbah and da Silva Eusébio, 1998 | AC |
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- + =
By formula: C5H5N2- + H+ = C5H6N2
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 1509. ± 8.8 | kJ/mol | G+TS | Taft and Bordwell, 1988 | gas phase; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 1478. ± 8.4 | kJ/mol | IMRE | Taft and Bordwell, 1988 | gas phase; B |
By formula: Li+ + C5H6N2 = (Li+ • C5H6N2)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 202. ± 10. | kJ/mol | CIDT | Rodgers, 2001 | RCD |
By formula: Na+ + C5H6N2 = (Na+ • C5H6N2)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 136. ± 4. | kJ/mol | CIDT | Rodgers, 2001 | RCD |
By formula: K+ + C5H6N2 = (K+ • C5H6N2)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 101. ± 3. | kJ/mol | CIDT | Rodgers, 2001 | RCD |
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) | 954.4 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
Quantity | Value | Units | Method | Reference | Comment |
Gas basicity | 922.6 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
8.7 ± 0.1 | EI | Stefanovic and Grutzmacher, 1974 | LLK |
9.03 ± 0.05 | EI | Gronneberg and Undheim, 1973 | LLK |
9.0 | CTS | Daisey and Sonnessa, 1972 | LLK |
8.44 | PE | Kobayashi and Nagakura, 1974 | Vertical value; LLK |
De-protonation reactions
C5H5N2- + =
By formula: C5H5N2- + H+ = C5H6N2
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 1509. ± 8.8 | kJ/mol | G+TS | Taft and Bordwell, 1988 | gas phase; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 1478. ± 8.4 | kJ/mol | IMRE | Taft and Bordwell, 1988 | gas 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
By formula: K+ + C5H6N2 = (K+ • C5H6N2)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 101. ± 3. | kJ/mol | CIDT | Rodgers, 2001 |
By formula: Li+ + C5H6N2 = (Li+ • C5H6N2)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 202. ± 10. | kJ/mol | CIDT | Rodgers, 2001 |
By formula: Na+ + C5H6N2 = (Na+ • C5H6N2)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 136. ± 4. | kJ/mol | CIDT | Rodgers, 2001 |
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, 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]
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, References
- Symbols used in this document:
Tboil Boiling point Tfus Fusion (melting) point ΔcH°solid Enthalpy of combustion of solid at standard conditions ΔfH°gas Enthalpy of formation of gas at standard conditions ΔfH°solid Enthalpy of formation of solid at standard conditions ΔfusH Enthalpy of fusion ΔrG° Free energy of reaction at standard conditions ΔrH° Enthalpy of reaction at standard conditions ΔsubH° Enthalpy of sublimation at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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