2-Butene, (Z)-
- Formula: C4H8
- Molecular weight: 56.1063
- IUPAC Standard InChIKey: IAQRGUVFOMOMEM-ARJAWSKDSA-N
- CAS Registry Number: 590-18-1
- 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. - Stereoisomers:
- Other names: (Z)-2-Butene; cis-Butene; cis-2-Butylene; cis-1,2-Dimethylethylene; cis-2-Butene; (Z)-2-C4H8; (2Z)-2-Butene; 2-Butene, cis-; Butene-2, cis-; 2-Butene, (2Z)-; (Z)-but-2-ene
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Gas phase ion energetics data
Go To: Top, 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 evaluated as indicated in comments:
L - Sharon G. Lias
Data compiled as indicated in comments:
LBLHLM - Sharon G. Lias, John E. Bartmess, Joel F. Liebman, John L. Holmes, Rhoda D. Levin, and W. Gary Mallard
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 C4H8+ (ion structure unspecified)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
IE (evaluated) | 9.11 ± 0.01 | eV | N/A | N/A | L |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
9.13 | PI | Traeger, 1986 | LBLHLM |
9.13 | PI | Traeger, 1984 | LBLHLM |
9.11 ± 0.02 | PI | Wood and Taylor, 1979 | LLK |
9.108 ± 0.008 | EQ | Lias and Ausloos, 1978 | LLK |
9.12 ± 0.02 | PE | Bieri, Burger, et al., 1977 | LLK |
9.124 ± 0.005 | PE | Masclet, Grosjean, et al., 1973 | LLK |
9.10 | EI | Lossing, 1972 | LLK |
9.07 | PE | Frost and Sandhu, 1971 | LLK |
9.119 | S | McDiarmid, 1969 | RDSH |
9.12 | PE | Dewar and Worley, 1969 | RDSH |
9.13 ± 0.01 | PI | Watanabe, Nakayama, et al., 1962 | RDSH |
9.13 | PI | Bralsford, Harris, et al., 1960 | RDSH |
9.32 ± 0.01 | PE | Krause, Taylor, et al., 1978 | Vertical value; LLK |
9.20 | PE | Wiberg, Ellison, et al., 1976 | Vertical value; LLK |
9.11 ± 0.03 | PE | Heilbronner, Hoshi, et al., 1976 | Vertical value; LLK |
9.36 | PE | Kimura, Katsumata, et al., 1975 | Vertical value; LLK |
9.4 | PE | White, Carlson, et al., 1974 | Vertical value; LLK |
9.29 | PE | Robin, Taylor, et al., 1973 | Vertical value; LLK |
Appearance energy determinations
Ion | AE (eV) | Other Products | Method | Reference | Comment |
---|---|---|---|---|---|
C2H4+ | 11.7 ± 0.25 | ? | EI | Meisels, Park, et al., 1970 | RDSH |
C2H5+ | 12.25 | C2H3 | EI | Omura, 1961 | RDSH |
C3H3+ | 13.75 | ? | EI | Omura, 1961 | RDSH |
C3H5+ | 11.25 | CH3 | PI | Traeger, 1984 | LBLHLM |
C3H5+ | 11.33 | CH3 | EI | Lossing, 1971 | LLK |
C4H7+ | 11.19 | H | PI | Traeger, 1986 | LBLHLM |
C4H7+ | 11.32 | H | EI | Lossing, 1972 | LLK |
Mass spectrum (electron ionization)
Go To: Top, 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: 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 | 18914 |
Gas Chromatography
Go To: Top, Gas phase ion energetics data, Mass spectrum (electron ionization), 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 | BPX-5 | 30. | 426. | Aflalaye, Sternberg, et al., 1995 | 12. m/0.15 mm/0.25 μm, H2 |
Capillary | CP Sil 5 CB | 20. | 425. | Do and Raulin, 1992 | 25. m/0.15 mm/2. μm, H2 |
Capillary | Squalane | 50. | 417.0 | Papazova, Milina, et al., 1988 | Column length: 50. m; Column diameter: 0.25 mm |
Capillary | DB-1 | 40. | 425. | Lubeck and Sutton, 1984 | 60. m/0.264 mm/0.25 μm, H2 |
Capillary | HP-PONA | 40. | 425. | Lubeck and Sutton, 1984 | 50. m/0.21 mm/0.5 μm, H2 |
Capillary | OV-1 | 20. | 418. | Nijs and Jacobs, 1981 | He; Column length: 150. m; Column diameter: 0.50 mm |
Capillary | Squalane | 50. | 416.5 | Bajus, Veselý, et al., 1979 | Column length: 100. m; Column diameter: 0.25 mm |
Capillary | Squalane | 70. | 416.5 | Bajus, Veselý, et al., 1979 | Column length: 100. m; Column diameter: 0.25 mm |
Capillary | Squalane | 50. | 416.3 | Bajus, Veselý, et al., 1979, 2 | Column length: 100. m; Column diameter: 0.25 mm |
Capillary | Squalane | 70. | 416.5 | Bajus, Veselý, et al., 1979, 2 | Column length: 100. m; Column diameter: 0.25 mm |
Capillary | Squalane | 50. | 416.85 | Pacáková and Koslík, 1978 | 50. m/0.2 mm/0.5 μm, N2 |
Packed | Squalane | 80. | 417. | Chrétien and Dubois, 1977 | |
Capillary | Squalane | 50. | 417. | Chretien and Dubois, 1976 | |
Capillary | Squalane | 100. | 427.3 | Lulova, Leont'eva, et al., 1976 | He; Column length: 120. m; Column diameter: 0.25 mm |
Capillary | Squalane | 50. | 417. | Rijks and Cramers, 1974 | N2; Column length: 100. m; Column diameter: 0.25 mm |
Capillary | Squalane | 70. | 417. | Rijks and Cramers, 1974 | N2; Column length: 100. m; Column diameter: 0.25 mm |
Capillary | Squalane | 40. | 411. | Matukuma, 1969 | N2; Column length: 91.4 m; Column diameter: 0.25 mm |
Packed | Squalane | 27. | 416. | Hively and Hinton, 1968 | He, Chromosorb P; Column length: 15. m; Column diameter: 0.25 mm |
Packed | Squalane | 49. | 417. | Hively and Hinton, 1968 | He, Chromosorb P; Column length: 15. m; Column diameter: 0.25 mm |
Packed | Squalane | 67. | 417. | Hively and Hinton, 1968 | He, Chromosorb P; Column length: 15. m; Column diameter: 0.25 mm |
Packed | Squalane | 86. | 418. | Hively and Hinton, 1968 | He, Chromosorb P; Column length: 15. m; Column diameter: 0.25 mm |
Packed | SE-30 | 70. | 427. | Widmer, 1967 | Diatoport S; Column length: 7.9 m |
Packed | SE-30 | 70. | 427. | Widmer, 1967 | Diatoport S; Column length: 7.9 m |
Kovats' RI, non-polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | Petrocol DH-100 | 428.2 | 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. | 481. | Widmer, 1967 | Diatoport P; Column length: 7.9 m |
Packed | Carbowax 20M | 70. | 468. | Widmer, 1967 | Diatoport P; Column length: 7.9 m |
Packed | Carbowax 20M | 70. | 468. | Widmer, 1967 | Diatoport P; Column length: 7.9 m |
Van Den Dool and Kratz RI, non-polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | Ultra-1 | 420. | Olson, Sinkevitch, et al., 1992 | 4. K/min; Tstart: -40. C; Tend: 230. C |
Capillary | Petrocol DH | 416.44 | White, Douglas, et al., 1992 | 100. m/0.25 mm/0.5 μm, He, 1. K/min; Tstart: 30. C; Tend: 220. C |
Capillary | Petrocol DH | 418.18 | White, Douglas, et al., 1992 | 100. m/0.25 mm/0.5 μm, He, 1. K/min; Tstart: 30. C; Tend: 220. C |
Van Den Dool and Kratz RI, non-polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | DB-5 | 411. | Zaikin and Borisov, 2002 | He; Column length: 30. m; Column diameter: 0.25 mm; Program: 30C => 5K/min=120C => 10C/min => 270C |
Normal alkane RI, non-polar column, isothermal
Column type | Active phase | Temperature (C) | I | Reference | Comment |
---|---|---|---|---|---|
Capillary | OV-101 | 40. | 417. | Li and Deng, 1998 | N2; Column length: 51. m; Column diameter: 0.25 mm |
Capillary | Methyl Silicone | 50. | 417. | N/A | N2; Column length: 74.6 m; Column diameter: 0.28 mm |
Packed | Methyl Silicone | 50. | 431. | Huguet, 1961 | Nitrogen, Celite C-22; Column length: 2.5 m |
Normal alkane RI, non-polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | Polydimethyl siloxane: CP-Sil 5 CB | 422. | 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 | Petrocol DH | 426. | Supelco, 2012 | 100. m/0.25 mm/0.50 μm, Helium, 20. C @ 15. min, 15. K/min, 220. C @ 30. min |
Capillary | PONA | 416. | Zhang, Ding, et al., 2009 | 50. m/0.20 mm/0.50 μm, Nitrogen, 35. C @ 15. min, 2. K/min, 200. C @ 10. min |
Capillary | OV-101 | 420. | Chupalov and Zenkevich, 1996 | N2, 3. K/min; Column length: 52. m; Column diameter: 0.26 mm; Tstart: 50. C; Tend: 220. C |
Capillary | SE-54 | 416. | Guan, Li, et al., 1995 | 60. C @ 2. min, 4. K/min; Column length: 50. m; Column diameter: 0.32 mm; Tend: 200. C |
Capillary | DB-1 | 416. | Ciccioli, Cecinato, et al., 1992 | 60. m/0.32 mm/1.2 μm, He, 30. C @ 10. min, 3. K/min; Tend: 240. C |
Normal alkane RI, non-polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | Polydimethyl siloxane | 417. | Junkes, Castanho, et al., 2003 | Program: not specified |
Capillary | PONA | 428. | Perkin Elmer Instruments, 2002 | Column length: 100. m; Phase thickness: 0.50 μm; Program: not specified |
Capillary | Methyl Silicone | 421. | Spieksma, 1999 | Program: not specified |
Capillary | Polydimethyl siloxanes | 420. | Zenkevich, Chupalov, et al., 1996 | Program: not specified |
Packed | SE-30 | 427. | Robinson and Odell, 1971 | N2, Chromosorb W; Column length: 6.1 m; Program: 50C910min) => 20C/min => 90(6min) => 10C/min => 150C(hold) |
Packed | Squalane | 428. | Robinson and Odell, 1971 | N2, Embacel; Column length: 3.0 m; Program: 25C(5min) => 2C/min => 35 => 4C/min => 95C(hold) |
References
Go To: Top, Gas phase ion energetics data, Mass spectrum (electron ionization), Gas Chromatography, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Traeger, 1986
Traeger, J.C.,
Heat of formation for the 1-methylallyl cation by photoionization mass spectrometry,
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Traeger, 1984
Traeger, J.C.,
A study of the allyl cation thermochemistry by photoionization mass spectrometry,
Int. J. Mass Spectrom. Ion Processes, 1984, 58, 259. [all data]
Wood and Taylor, 1979
Wood, K.V.; Taylor, J.W.,
A photoionization mass spectrometric study of autoionization in ethylene and trans-2-butene,
Int. J. Mass Spectrom. Ion Phys., 1979, 30, 307. [all data]
Lias and Ausloos, 1978
Lias, S.G.; Ausloos, P.J.,
eIonization energies of organic compounds by equilibrium measurements,
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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]
Masclet, Grosjean, et al., 1973
Masclet, P.; Grosjean, D.; Mouvier, G.,
Alkene ionization potentials. Part I. Quantitative determination of alkyl group structural effects,
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Lossing, 1972
Lossing, F.P.,
Free radicals by mass spectrometry. XLV. Ionization potentials and heats of formation of C3H3, C3H5, and C4H7 radicals and ions,
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Frost and Sandhu, 1971
Frost, D.C.; Sandhu, J.S.,
Ionization potentials of ethylene and some methyl-substituted ethylenes as determined by photoelectron spectroscopy,
Indian J. Chem., 1971, 9, 1105. [all data]
McDiarmid, 1969
McDiarmid, R.,
Rydberg progressions in cis- and trans-butene,
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Dewar and Worley, 1969
Dewar, M.J.S.; Worley, S.D.,
Photoelectron spectra of molecules. I. Ionization potentials of some organic molecules and their interpretation,
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Watanabe, Nakayama, et al., 1962
Watanabe, K.; Nakayama, T.; Mottl, J.,
Ionization potentials of some molecules,
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Bralsford, Harris, et al., 1960
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The effect of fluorine on the electronic spectra and ionization potentials of molecules,
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An analysis of the effects of alkyl substituents on the ionization potentials of n-alkenes,
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Wiberg, K.B.; Ellison, G.B.; Wendoloski, J.J.; Brundle, C.R.; Kuebler, N.A.,
Electronic states of organic molecules. 3. Photoelectron spectra of cycloalkenes and methylenecycloalkanes,
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Alkyl-induced, natural hypsochromic shifts of the 2A←2X and 2B←2X transitions of azulene and naphthalene radical cations,
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UV photoelectron spectra and sum rule consideration; out-of-plane orbitals of unsaturated compounds with planar-skeleton structure,
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Angular distribution of the photoelectron spectra for ethylene, propylene, butene and butadiene,
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Ionization and dissociation of C4H8 isomers,
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Omura, I.,
Mass spectra at low ionizing voltage and bond dissociation energies of molecular ions from hydrocarbons,
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Free radicals by mass spectrometry. XLIII. Ionization potentials and ionic heats of formation for vinyl, allyl, and benzyl radicals,
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Aflalaye, A.; Sternberg, R.; Raulin, F.; Vidal-Madjar, C.,
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Kovats Retention Indices of Selected Olefins on Bonded Phase Fused Silica Capillaries,
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On-Line Single Run Analysis of Effluents from a Fischer-Tropsch Reactor,
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Capillary reaction gas chromatography. I. Catalytic decomposition of hydrocarbons,
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Topological analysis of gas-liquid chromatographic behavior of alkenes,
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New Perspectives in the Prediction of Kovats Indices,
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High precision capillary gas chromatography of hydrocarbons,
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Matukuma, A.,
Retention indices of alkanes through C10 and alkenes through C8 and relation between boiling points and retention data,
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Variation of the retention index with temperature on squalane substrates,
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Widmer, H.,
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Haagen-Smit Laboratory,
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Olson, K.L.; Sinkevitch, R.M.; Sloane, T.M.,
Speciation and Quantitation of Hydrocarbons in Gasoline Engine Exhaust,
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Characterization of synthetic gasoline from the chloromethane-zeolite reaction,
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Zaikin, V.G.; Borisov, R.S.,
Chromatographic-mass spectrometric analysis of Fishcer-Tropsch synthesis products,
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Li, H.; Deng, C.,
Qualitative analysis of light components of gasoline cracking using Kovats retention indices,
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Huguet, M.,
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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]
Supelco, 2012
Supelco, CatalogNo. 24160-U,
Petrocol DH Columns. Catalog No. 24160-U, 2012, retrieved from http://www.sigmaaldrich.com/etc/medialib/docs/Supelco/Datasheet/1/w97949.Par.0001.File.tmp/w97949.pdf. [all data]
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Zhang, X.; Ding, L.; Sun, Z.; Song, L.; Sun, T.,
Study on quantitative structure-retention relationships for hydrocarbons in FCC gasoline,
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Chupalov, A.A.; Zenkevich, I.G.,
Chromatographic Characterization of Structural Transformations of Organic Compounds in Diels-Alder Reaction. Aliphatic Dienes and Dienophyls,
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Guan, Y.; Li, L.; Zhou, L.,
Live retention database for compound identification in capillary gas chromatography,
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Ciccioli, Cecinato, et al., 1992
Ciccioli, P.; Cecinato, A.; Brancaleoni, E.; Frattoni, M.; Liberti, A.,
Use of carbon adsorption traps combined with high resolution gas chromatography - mass spectrometry for the analysis of polar and non-polar C4-C14 hydrocarbons involved in photochemical smog formation,
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. [all data]
Junkes, Castanho, et al., 2003
Junkes, B.S.; Castanho, R.D.M.; Amboni, C.; Yunes, R.A.; Heinzen, V.E.F.,
Semiempirical Topological Index: A Novel Molecular Descriptor for Quantitative Structure-Retention Relationship Studies,
Internet Electronic Journal of Molecular Design, 2003, 2, 1, 33-49. [all data]
Perkin Elmer Instruments, 2002
Perkin Elmer Instruments,
Detailed hydrocarbon analysis (DHAX) Model 4015, 2002, retrieved from http://www.perkinelmer.com/instruments. [all data]
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Spieksma, W.,
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Notes
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- Symbols used in this document:
AE Appearance energy IE (evaluated) Recommended ionization energy - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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