Pyridazine
- Formula: C4H4N2
- Molecular weight: 80.0880
- IUPAC Standard InChIKey: PBMFSQRYOILNGV-UHFFFAOYSA-N
- CAS Registry Number: 289-80-5
- 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: Orthodiazine; 1,2-Diazabenzene; 1,2-Diazine
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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, 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
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°gas | 278.4 ± 1.3 | kJ/mol | Ccb | Tjebbes, 1962 |
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°liquid | 224.9 ± 0.92 | kJ/mol | Ccb | Tjebbes, 1962 | |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°liquid | -2370.6 ± 0.92 | kJ/mol | Ccb | Tjebbes, 1962 |
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 | 481.2 | K | N/A | Weast and Grasselli, 1989 | BS |
Tboil | 480.35 | K | N/A | Lecat, 1947 | Uncertainty assigned by TRC = 0.6 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 53.5 ± 0.4 | kJ/mol | C | Tjebbes, Mollberg, et al., 1962 | AC |
ΔvapH° | 53.5 ± 0.4 | kJ/mol | C | Tjebbes, 1962 | ALS |
ΔvapH° | 53.5 | kJ/mol | N/A | Tjebbes, 1962 | DRB |
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 by: John E. Bartmess
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
C4H3N2- + =
By formula: C4H3N2- + H+ = C4H4N2
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 1600. ± 10. | kJ/mol | TDEq | Meot-ner and Kafafi, 1988 | gas phase; Pyridazine. Anchored to 88MEO scale, not the "87 Acidity Scale". |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 1564.8 ± 2.9 | kJ/mol | N/A | Wren, Vogelhuber, et al., 2012 | gas phase |
ΔrG° | 1562. ± 8.4 | kJ/mol | TDEq | Meot-ner and Kafafi, 1988 | gas phase; Pyridazine. Anchored to 88MEO scale, not the "87 Acidity Scale". |
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
L - 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
View reactions leading to C4H4N2+ (ion structure unspecified)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
IE (evaluated) | 8.74 ± 0.11 | eV | N/A | N/A | L |
Quantity | Value | Units | Method | Reference | Comment |
Proton affinity (review) | 907.2 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
Quantity | Value | Units | Method | Reference | Comment |
Gas basicity | 877.1 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
Electron affinity determinations
EA (eV) | Method | Reference | Comment |
---|---|---|---|
0.01201 | EFD | Suess, Liu, et al., 2003 | B |
>-0.31699 | ETS | Nenner and Schultz, 1975 | Pyridazine. EA estimated as 0.25 eV based on solution phase electrochemical correlations; B |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
8.64 | PE | Gleiter, Heilbronner, et al., 1972 | LLK |
8.706 ± 0.001 | PE | Asbrink, Fridh, et al., 1972 | LLK |
8.90 | PE | Dewar and Worley, 1969 | RDSH |
8.71 ± 0.01 | PI | Yencha and El-Sayed, 1968 | RDSH |
9.31 | PE | Suffolk, 1974 | Vertical value; LLK |
9.31 | PE | Gleiter, Heilbronner, et al., 1970 | Vertical value; RDSH |
Appearance energy determinations
Ion | AE (eV) | Other Products | Method | Reference | Comment |
---|---|---|---|---|---|
C2H2+ | 14.94 ± 0.10 | ? | EI | Momigny, Urbain, et al., 1965 | RDSH |
C2H2+ | 15.79 ± 0.05 | ? | EI | Momigny, Urbain, et al., 1965 | RDSH |
C2H2+ | 15.23 ± 0.10 | ? | EI | Momigny, Urbain, et al., 1965 | RDSH |
C4H2+ | 13.67 ± 0.10 | N2+H2 | EI | Momigny, Urbain, et al., 1965 | RDSH |
C4H3+ | 13.84 ± 0.10 | N2+H | EI | Momigny, Urbain, et al., 1965 | RDSH |
C4H4+ | 11.64 ± 0.05 | N2 | EI | Momigny, Urbain, et al., 1965 | RDSH |
De-protonation reactions
C4H3N2- + =
By formula: C4H3N2- + H+ = C4H4N2
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 1600. ± 10. | kJ/mol | TDEq | Meot-ner and Kafafi, 1988 | gas phase; Pyridazine. Anchored to 88MEO scale, not the "87 Acidity Scale".; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 1564.8 ± 2.9 | kJ/mol | N/A | Wren, Vogelhuber, et al., 2012 | gas phase; B |
ΔrG° | 1562. ± 8.4 | kJ/mol | TDEq | Meot-ner and Kafafi, 1988 | gas phase; Pyridazine. Anchored to 88MEO scale, not the "87 Acidity Scale".; B |
Gas Chromatography
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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
Kovats' RI, non-polar column, isothermal
Column type | Active phase | Temperature (C) | I | Reference | Comment |
---|---|---|---|---|---|
Capillary | OV-101 | 110. | 915. | Golovnya, Kuz'menko, et al., 2000 | He; Phase thickness: 0.4 μm |
Capillary | OV-101 | 110. | 915. | Zhuravleva, 2000 | 50. m/0.3 mm/0.4 μm, He |
Capillary | OV-101 | 110. | 915. | Golovnya, Kuz'menko, et al., 1999 | 50. m/0.3 mm/0.4 μm, He |
Van Den Dool and Kratz RI, non-polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Packed | SE-30 | 894. | Peng, Ding, et al., 1988 | He, Supelcoport and Chromosorb, 40. C @ 4. min, 10. K/min, 250. C @ 60. min; Column length: 3.05 m |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Gas Chromatography, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Tjebbes, 1962
Tjebbes, J.,
The heats of combustion and formation of the three diazines and their resonance energies,
Acta Chem. Scand., 1962, 16, 916-921. [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]
Lecat, 1947
Lecat, M.,
Some azeotropes of which one constituant is heterocyclic nitrogen,
Ann. Soc. Sci. Bruxelles, Ser. 1, 1947, 61, 73. [all data]
Tjebbes, Mollberg, et al., 1962
Tjebbes, Jan; Mollberg, René; Lindberg, Bengt; McKay, James; Theander, Olof; Flood, H.,
The Heats of Combustion and Formation of the Three Diazines and their Resonance Energies.,
Acta Chem. Scand., 1962, 16, 916-921, https://doi.org/10.3891/acta.chem.scand.16-0916
. [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]
Wren, Vogelhuber, et al., 2012
Wren, S.W.; Vogelhuber, K.M.; Garver, J.M.; Kato, S.; Sheps, L.; Bierbaum, V.M.; Lineberger, W.C.,
C-H Bond Strengths and Acidities in Aromatic Systems: Effects of Nitrogen Incorporation in Mono-, Di-, and Triazines,
J. Am. Chem. Soc., 2012, 134, 15, 6584-6595, https://doi.org/10.1021/ja209566q
. [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]
Suess, Liu, et al., 2003
Suess, L.; Liu, Y.; Parthasarathy, R.; Dunning, F.B.,
Dipole-bound negative ions: Collisional destruction and blackbody-radiation-induced photodetachment,
J. Chem. Phys., 2003, 119, 24, 12890-12894, https://doi.org/10.1063/1.1628215
. [all data]
Nenner and Schultz, 1975
Nenner, I.; Schultz, G.J.,
Temporary negative ions and electron affinities of benzene and N-heterocyclic molecules: Pyridine, pyridazine, pyrimidine, pyrazine, and s-triazine,
J. Chem. Phys., 1975, 62, 1747. [all data]
Gleiter, Heilbronner, et al., 1972
Gleiter, R.; Heilbronner, E.; Hornung, V.,
Photoelectron spectra of azabenzenes azanaphthalenes: I. Pyridine, diazines s-triazine and s-tetrazine,
Helv. Chim. Acta, 1972, 55, 255. [all data]
Asbrink, Fridh, et al., 1972
Asbrink, L.; Fridh, C.; Jonsson, B.O.; Lindholm, E.,
Rydberg series in small molecules. XVII. Photoelectron, UV, mass and electron impact spectra of pyridazine,
Int. J. Mass Spectrom. Ion Phys., 1972, 8, 229. [all data]
Dewar and Worley, 1969
Dewar, M.J.S.; Worley, S.D.,
Photoelectron spectra of molecules. II.The ionization potentials of azabenzenes and azanaphthalenes,
J. Chem. Phys., 1969, 51, 263. [all data]
Yencha and El-Sayed, 1968
Yencha, A.J.; El-Sayed, M.A.,
Lowest ionization potentials of some nitrogen heterocyclics,
J. Chem. Phys., 1968, 48, 3469. [all data]
Suffolk, 1974
Suffolk, R.J.,
The photoelectron spectra of the perfluorodiazines,
J. Electron Spectrosc. Relat. Phenom., 1974, 3, 53. [all data]
Gleiter, Heilbronner, et al., 1970
Gleiter, R.; Heilbronner, E.; Hornung, V.,
Lone pair interaction in pyridazine, pyrimidine, and pyrazine,
Angew. Chem. Int. Ed. Engl., 1970, 9, 901. [all data]
Momigny, Urbain, et al., 1965
Momigny, J.; Urbain, J.; Wankenne, H.,
Les effets de l'impact electronique sur la pyridine et les diazines isomeres,
Bull. Soc. Roy. Sci. Liege, 1965, 34, 337. [all data]
Golovnya, Kuz'menko, et al., 2000
Golovnya, R.V.; Kuz'menko, T.E.; Krikunova, N.I.,
The influence of alkyl substituents on the chromatographic indicator of self-association of N-containing heterocyclic compounds,
Russ. Chem. Bull. (Engl. Transl.), 2000, 49, 2, 321-324, https://doi.org/10.1007/BF02494681
. [all data]
Zhuravleva, 2000
Zhuravleva, I.L.,
Evaluation of the polarity and boiling points of nitrogen-containing heterocyclic compounds by gas chromatography,
Russ. Chem. Bull. (Engl. Transl.), 2000, 49, 2, 325-328, https://doi.org/10.1007/BF02494682
. [all data]
Golovnya, Kuz'menko, et al., 1999
Golovnya, R.V.; Kuz'menko, T.E.; Zhuravleva, I.L.,
Gas chromatographic indicator of the ability of five- and six-membered heterocyclic nitrogen-containing compounds for self-association in pure liquids,
Russ. Chem. Bull. (Engl. Transl.), 1999, 48, 4, 726-729, https://doi.org/10.1007/BF02496256
. [all data]
Peng, Ding, et al., 1988
Peng, C.T.; Ding, S.F.; Hua, R.L.; Yang, Z.C.,
Prediction of Retention Indexes I. Structure-Retention Index Relationship on Apolar Columns,
J. Chromatogr., 1988, 436, 137-172, https://doi.org/10.1016/S0021-9673(00)94575-8
. [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, Gas Chromatography, References
- Symbols used in this document:
AE Appearance energy EA Electron affinity IE (evaluated) Recommended ionization energy Tboil Boiling point ΔcH°liquid Enthalpy of combustion of liquid at standard conditions ΔfH°gas Enthalpy of formation of gas at standard conditions ΔfH°liquid Enthalpy of formation of liquid at standard conditions ΔrG° Free energy of reaction at standard conditions ΔrH° Enthalpy of reaction at standard conditions ΔvapH° Enthalpy of vaporization at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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