1,2-Butadiene
- Formula: C4H6
- Molecular weight: 54.0904
- IUPAC Standard InChI: InChI=1S/C4H6/c1-3-4-2/h4H,1H2,2H3
- IUPAC Standard InChIKey: QNRMTGGDHLBXQZ-UHFFFAOYSA-N
- CAS Registry Number: 590-19-2
- 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: Allene, methyl-; Methylallene; CH2=C=CHCH3; Buta-1,2-diene
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Gas phase ion energetics data
Go To: Top, Mass spectrum (electron ionization), UV/Visible spectrum, 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 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
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron
View reactions leading to C4H6+ (ion structure unspecified)
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| Proton affinity (review) | 186.2 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
| Quantity | Value | Units | Method | Reference | Comment |
| Gas basicity | 179.2 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
Ionization energy determinations
| IE (eV) | Method | Reference | Comment |
|---|---|---|---|
| 9.03 | PE | Beez, Bieri, et al., 1973 | LLK |
| 9.23 ± 0.02 | PI | Parr and Elder, 1968 | RDSH |
| 9.33 ± 0.02 | PE | Bieri, Burger, et al., 1977 | Vertical value; LLK |
| 9.0 | PE | White, Carlson, et al., 1974 | Vertical value; LLK |
| 9.33 | PE | Brogli, Crandall, et al., 1973 | Vertical value; LLK |
Appearance energy determinations
| Ion | AE (eV) | Other Products | Method | Reference | Comment |
|---|---|---|---|---|---|
| CH3+ | 14.4 ± 0.2 | ? | EI | Collin and Lossing, 1957 | RDSH |
| C3H3+ | 10.86 ± 0.04 | CH3 | PI | Parr and Elder, 1968 | RDSH |
| C4H5+ | 11.04 ± 0.04 | H | PI | Parr and Elder, 1968 | RDSH |
De-protonation reactions
C4H5- + =
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 384.3 ± 2.1 | kcal/mol | G+TS | N/A | gas phase; Relative to dGacid(MeOH)= 375. Acid: MeCH=C=CH2; B |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrG° | 376.2 ± 2.0 | kcal/mol | IMRE | N/A | gas phase; Relative to dGacid(MeOH)= 375. Acid: MeCH=C=CH2; B |
Mass spectrum (electron ionization)
Go To: Top, Gas phase ion energetics data, UV/Visible spectrum, 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: NIST Mass Spectrometry Data Center, William E. Wallace, director
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. |
|---|---|
| NIST MS number | 18905 |
UV/Visible spectrum
Go To: Top, Gas phase ion energetics data, 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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Additional Data
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| Source | Jones and Taylor, 1955 |
|---|---|
| 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. 2454 |
| Instrument | Beckman DU |
| Melting point | -136.2 |
| Boiling point | 10.9 |
Gas Chromatography
Go To: Top, Gas phase ion energetics data, 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, non-polar column, isothermal
| Column type | Active phase | Temperature (C) | I | Reference | Comment |
|---|---|---|---|---|---|
| Capillary | Squalane | 50. | 428.5 | Bajus, Veselý, et al., 1979 | Column length: 100. m; Column diameter: 0.25 mm |
| Capillary | Squalane | 70. | 427.9 | Bajus, Veselý, et al., 1979 | Column length: 100. m; Column diameter: 0.25 mm |
| Packed | Squalane | 27. | 429. | Hively and Hinton, 1968 | He, Chromosorb P; Column length: 15. m; Column diameter: 0.25 mm |
| Packed | Squalane | 49. | 430. | Hively and Hinton, 1968 | He, Chromosorb P; Column length: 15. m; Column diameter: 0.25 mm |
| Packed | Squalane | 67. | 430. | Hively and Hinton, 1968 | He, Chromosorb P; Column length: 15. m; Column diameter: 0.25 mm |
| Packed | Squalane | 86. | 430. | Hively and Hinton, 1968 | He, Chromosorb P; Column length: 15. m; Column diameter: 0.25 mm |
| Packed | SE-30 | 70. | 448. | Widmer, 1967 | Diatoport S; Column length: 7.9 m |
| Packed | Squalane | 26. | 427. | Zulaïca and Guiochon, 1966 | Column length: 10. m |
Kovats' RI, non-polar column, custom temperature program
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | Petrocol DH-100 | 450. | Haagen-Smit Laboratory, 1997 | He; Column length: 100. m; Column diameter: 0.2 mm; Program: 5C(10min) => 5C/min => 50C(48min) => 1.5C/min => 195C(91min) |
Kovats' RI, polar column, isothermal
| Column type | Active phase | Temperature (C) | I | Reference | Comment |
|---|---|---|---|---|---|
| Packed | Carbowax 20M | 130. | 562. | Widmer, 1967 | Diatoport P; Column length: 7.9 m |
| Packed | Carbowax 20M | 70. | 540. | Widmer, 1967 | Diatoport P; Column length: 7.9 m |
Normal alkane RI, non-polar column, temperature ramp
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | Polydimethyl siloxane: CP-Sil 5 CB | 441. | Bramston-Cook, 2013 | 60. m/0.25 mm/1.0 μm, Helium, 45. C @ 1.45 min, 3.6 K/min, 210. C @ 2.72 min |
| Capillary | OV-101 | 427. | Zenkevich, 2005 | 25. m/0.20 mm/0.10 μm, N2/He, 6. K/min; Tstart: 50. C; Tend: 250. C |
References
Go To: Top, Gas phase ion energetics data, 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.
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]
Beez, Bieri, et al., 1973
Beez, M.; Bieri, G.; Bock, H.; Heilbronner, E.,
The ionization potentials of butadiene, hexatriene, andtheir methyl derivatives: evidence for through space interaction between double bond π-orbitals and non-bonded pseudo-π orbitals of methyl groups?,
Helv. Chim. Acta, 1973, 56, 1028. [all data]
Parr and Elder, 1968
Parr, A.C.; Elder, F.A.,
Photoionization of 1,3butadiene, 1,2-butadiene, allene, and propyne,
J. Chem. Phys., 1968, 49, 2659. [all data]
Bieri, Burger, et al., 1977
Bieri, G.; Burger, F.; Heilbronner, E.; Maier, J.P.,
Valence ionization enrgies of hydrocarbons,
Helv. Chim. Acta, 1977, 60, 2213. [all data]
White, Carlson, et al., 1974
White, R.M.; Carlson, T.A.; Spears, D.P.,
Angular distribution of the photoelectron spectra for ethylene, propylene, butene and butadiene,
J. Electron Spectrosc. Relat. Phenom., 1974, 3, 59. [all data]
Brogli, Crandall, et al., 1973
Brogli, F.; Crandall, J.K.; Heilbronner, E.; Kloster-Jensen, E.; Sojka, S.A.,
The photoelectron spectra of methyl-substituted allenes and of tetramethyl-bisallenyl,
J. Electron Spectrosc. Relat. Phenom., 1973, 2, 455. [all data]
Collin and Lossing, 1957
Collin, J.; Lossing, F.P.,
Ionization and dissociation of allene, propyne, 1-butyne, and 1,2- and 1,3-butadienes by electron impact; the C3H3+ ion,
J. Am. Chem. Soc., 1957, 79, 5848. [all data]
Jones and Taylor, 1955
Jones, L.C., Jr.; Taylor, L.W.,
Far ultraviolet absorption spectra of unsaturated and aromatic hydrocarbons,
Anal. Chem., 1955, 27, 2, 228-237. [all data]
Bajus, Veselý, et al., 1979
Bajus, M.; Veselý, V.; Leclercq, P.A.; Rijks, J.A.,
Steam cracking of hydrocarbons. 2. Pyrolysis of methylcyclohexane,
Ind. Eng. Chem. Prod. Res. Dev., 1979, 18, 2, 135-142, https://doi.org/10.1021/i360070a012
. [all data]
Hively and Hinton, 1968
Hively, R.A.; Hinton, R.E.,
Variation of the retention index with temperature on squalane substrates,
J. Gas Chromatogr., 1968, 6, 4, 203-217, https://doi.org/10.1093/chromsci/6.4.203
. [all data]
Widmer, 1967
Widmer, H.,
Gas chromatographic identification of hydrocarbons using retention indices,
J. Gas Chromatogr., 1967, 5, 10, 506-510, https://doi.org/10.1093/chromsci/5.10.506
. [all data]
Zulaïca and Guiochon, 1966
Zulaïca, J.; Guiochon, G.,
Analyse des hauts polymères par chromatographie en phase gazeuse de leurs produits de pyrolyse. II. Application à quelques hydrocarbures macromoléculaires purs,
Bull. Soc. Chim. Fr., 1966, 4, 1351-1363. [all data]
Haagen-Smit Laboratory, 1997
Haagen-Smit Laboratory,
Procedure for the detailed hydrocarbon analysis of gasolines by single column high efficiency (capillary) column gas chromatography, SOP NO. MLD 118, Revision No. 1.1, California Environmental Protection Agency, Air Resources Board, El Monte, California, 1997, 22. [all data]
Bramston-Cook, 2013
Bramston-Cook, R.,
Kovats indices for C2-C13 hydrocarbons and selected oxygenated/halocarbons with 100 % dimethylpolysiloxane columns, 2013, retrieved from http://lotusinstruments.com/monographs/List .... [all data]
Zenkevich, 2005
Zenkevich, I.G.,
Experimentally measured retention indices., 2005. [all data]
Notes
Go To: Top, Gas phase ion energetics data, Mass spectrum (electron ionization), UV/Visible spectrum, Gas Chromatography, References
- Symbols used in this document:
AE Appearance energy ΔrG° Free energy of reaction at standard conditions ΔrH° Enthalpy of reaction at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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