1,3-Butadiene

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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:
HL - Edward P. Hunter and Sharon G. Lias
L - Sharon G. Lias

Data compiled as indicated in comments:
B - John E. Bartmess
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 C4H6+ (ion structure unspecified)

Quantity Value Units Method Reference Comment
IE (evaluated)9.072 ± 0.007eVN/AN/AL
Quantity Value Units Method Reference Comment
Proton affinity (review)187.2kcal/molN/AHunter and Lias, 1998HL
Quantity Value Units Method Reference Comment
Gas basicity181.1kcal/molN/AHunter and Lias, 1998HL

Ionization energy determinations

IE (eV) Method Reference Comment
9.082 ± 0.004SMallard, Miller, et al., 1983LBLHLM
9.07PEMasclet, Mouvier, et al., 1981LLK
9.09PEKimura, Katsumata, et al., 1981LLK
9.03EIDannacher, Flamme, et al., 1980LLK
9.03PEBieri and Asbrink, 1980LLK
9.03 ± 0.02PEBieri, Burger, et al., 1977LLK
9.0691SMcDiarmid, 1976LLK
9.06PEBrundle and Robin, 1970RDSH
9.06 ± 0.02PIMatthews and Warneck, 1969RDSH
9.09 ± 0.05PEEland, 1969RDSH
9.07 ± 0.02PIParr and Elder, 1968RDSH
9.07PEDewar and Worley, 1968RDSH
~9.2DERDewar and Worley, 1968RDSH
9.18 ± 0.04EIBock and Seidl, 1968RDSH
9.09 ± 0.03EIFranklin and Mogenis, 1967RDSH
9.075 ± 0.005PIBrehm, 1966RDSH
9.07 ± 0.01PIWatanabe, 1954RDSH
9.06 ± 0.01SPrice and Walsh, 1940RDSH
9.03PESchmidt, Schweig, et al., 1976Vertical value; LLK

Appearance energy determinations

Ion AE (eV) Other Products MethodReferenceComment
C2H2+15.4 ± 0.1?EIDannacher, Flamme, et al., 1980LLK
C2H2+16.5 ± 0.1?EIFranklin and Mogenis, 1967RDSH
C2H3+15.1 ± 0.1?EIDannacher, Flamme, et al., 1980LLK
C2H3+15.7 ± 0.2?EIFranklin and Mogenis, 1967RDSH
C2H4+12.6 ± 0.1C2H2EIDannacher, Flamme, et al., 1980LLK
C2H4+12.5 ± 0.1C2H2PIBrehm, 1966RDSH
C3H+12.44?EIField, Franklin, et al., 1957RDSH
C3H3+11.3 ± 0.1CH3EIDannacher, Flamme, et al., 1980LLK
C3H3+11.39 ± 0.03CH3PIMatthews and Warneck, 1969RDSH
C3H3+11.40 ± 0.02CH3PIParr and Elder, 1968RDSH
C3H3+11.35 ± 0.05CH3PIBrehm, 1966RDSH
C4H+15.752H2+HEIField, Franklin, et al., 1957RDSH
C4H2+16.87 ± 0.05?EIFranklin and Mogenis, 1967RDSH
C4H3+14.9 ± 0.1H3EIDannacher, Flamme, et al., 1980LLK
C4H3+16.25 ± 0.05H2+HEIFranklin and Mogenis, 1967RDSH
C4H4+13.0 ± 0.1H2EIDannacher, Flamme, et al., 1980LLK
C4H4+13.84 ± 0.07H2EIFranklin and Mogenis, 1967RDSH
C4H5+11.4 ± 0.1HPIDannacher, Flamme, et al., 1980LLK
C4H5+11.56 ± 0.04HPIParr and Elder, 1968RDSH
C4H5+11.39 ± 0.05HPIBrehm, 1966RDSH

De-protonation reactions

C4H5- + Hydrogen cation = 1,3-Butadiene

By formula: C4H5- + H+ = C4H6

Quantity Value Units Method Reference Comment
Δr399.5 ± 3.1kcal/molG+TSDevisser, Dekoning, et al., 1995gas phase; B
Quantity Value Units Method Reference Comment
Δr391.3 ± 3.0kcal/molIMRBDevisser, Dekoning, et al., 1995gas phase; B

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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NIST MS number 18901

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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

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Column type Active phase Temperature (C) I Reference Comment
CapillaryBPX-530.400.Aflalaye, Sternberg, et al., 199512. m/0.15 mm/0.25 μm, H2
CapillaryBPX-530.400.Aflalaye, Sternberg, et al., 199512. m/0.15 mm/0.25 μm, H2
CapillaryCP Sil 5 CB20.394.3Do and Raulin, 199225. m/0.15 mm/2. μm, H2
CapillarySE-3060.397.Bredael, 1982Column length: 100. m; Column diameter: 0.5 mm
CapillarySqualane50.385.6Schröder, 1980 
PackedSqualane27.386.Hively and Hinton, 1968He, Chromosorb P; Column length: 15. m; Column diameter: 0.25 mm
PackedSqualane49.386.Hively and Hinton, 1968He, Chromosorb P; Column length: 15. m; Column diameter: 0.25 mm
PackedSqualane67.387.Hively and Hinton, 1968He, Chromosorb P; Column length: 15. m; Column diameter: 0.25 mm
PackedSqualane86.388.Hively and Hinton, 1968He, Chromosorb P; Column length: 15. m; Column diameter: 0.25 mm
PackedSE-3070.405.Widmer, 1967Diatoport S; Column length: 7.9 m
PackedSqualane26.389.Zulaïca and Guiochon, 1966Column length: 10. m

Kovats' RI, non-polar column, custom temperature program

View large format table.

Column type Active phase I Reference Comment
CapillaryPetrocol DH-100393.Haagen-Smit Laboratory, 1997He; Column length: 100. m; Column diameter: 0.2 mm; Program: 5C(10min) => 5C/min => 50C(48min) => 1.5C/min => 195C(91min)
CapillaryDB-1395.Hoekman, 199360. m/0.32 mm/1.0 μm, He; Program: -40 C for 12 min; -40 - 125 C at 3 deg.min; 125-185 C at 6 deg/min; 185 - 220 C at 20 deg/min; hold 220 C for 2 min

Kovats' RI, polar column, isothermal

View large format table.

Column type Active phase Temperature (C) I Reference Comment
PackedCarbowax 20M130.507.Widmer, 1967Diatoport P; Column length: 7.9 m
PackedCarbowax 20M70.487.Widmer, 1967Diatoport P; Column length: 7.9 m

Van Den Dool and Kratz RI, non-polar column, temperature ramp

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Column type Active phase I Reference Comment
CapillaryPetrocol DH403.White, Hackett, et al., 1992100. m/0.25 mm/0.5 μm, He, 1. K/min; Tstart: 30. C; Tend: 220. C
PackedSE-30395.Fischer and Kusch, 1990Chromosorb W AW (80-100 mesh), 5. K/min; Column length: 1.5 m; Tstart: 60. C; Tend: 280. C

Van Den Dool and Kratz RI, non-polar column, custom temperature program

View large format table.

Column type Active phase I Reference Comment
PackedSE-30395.Peng, Ding, et al., 1988Supelcoport; Chromosorb; Column length: 3.05 m; Program: 40C(5min) => 10C/min => 200C or 250C (60min)

Normal alkane RI, non-polar column, isothermal

View large format table.

Column type Active phase Temperature (C) I Reference Comment
CapillarySqualane70.390.Schomburg, 1966 
PackedMethyl Silicone50.412.Huguet, 1961Nitrogen, Celite C-22; Column length: 2.5 m

Normal alkane RI, non-polar column, temperature ramp

View large format table.

Column type Active phase I Reference Comment
CapillaryPolydimethyl siloxane: CP-Sil 5 CB394.Bramston-Cook, 201360. m/0.25 mm/1.0 μm, Helium, 45. C @ 1.45 min, 3.6 K/min, 210. C @ 2.72 min
CapillaryUltra-ALLOY-5395.Tsuge, Ohtan, et al., 201130. m/0.25 mm/0.25 μm, 40. C @ 2. min, 20. K/min, 320. C @ 13. min
CapillaryOV-101389.Zenkevich, 200525. m/0.20 mm/0.10 μm, N2/He, 6. K/min; Tstart: 50. C; Tend: 250. C
CapillaryOV-101398.Chupalov and Zenkevich, 1996N2, 3. K/min; Column length: 52. m; Column diameter: 0.26 mm; Tstart: 50. C; Tend: 220. C

Normal alkane RI, non-polar column, custom temperature program

View large format table.

Column type Active phase I Reference Comment
CapillaryMethyl Silicone395.Blunden, Aneja, et al., 200560. m/0.32 mm/1.0 μm, Helium; Program: -50 0C (2 min) 8 0C/min -> 200 0C (7.75 min) 25 0C -> 225 0C (8 min)
CapillaryPONA396.Perkin Elmer Instruments, 2002Column length: 100. m; Phase thickness: 0.50 μm; Program: not specified
CapillaryOV-101390.Zenkevich, 1998He; Column length: 25. m; Column diameter: 0.20 mm; Program: not specified
CapillaryOV-101392.Zenkevich, 1998He; Column length: 25. m; Column diameter: 0.20 mm; Program: not specified
CapillarySPB-1393.Flanagan, Streete, et al., 199760. m/0.53 mm/5. μm, He; Program: 40C(6min) => 5C/min => 80C => 10C/min => 200C
PackedSE-30395.Robinson and Odell, 1971N2, Chromosorb W; Column length: 6.1 m; Program: 50C910min) => 20C/min => 90(6min) => 10C/min => 150C(hold)
PackedSqualane404.Robinson and Odell, 1971N2, 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.

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]

Mallard, Miller, et al., 1983
Mallard, W.G.; Miller, J.H.; Smyth, K.C., The ns Rydberg series of 1,3-trans-butadiene observed using multiphoton ionization, J. Chem. Phys., 1983, 79, 5900. [all data]

Masclet, Mouvier, et al., 1981
Masclet, P.; Mouvier, G.; Bocquet, J.F., Effets electroniques et effets steriques dus a la substitution alcoyle dans les dienes conjugues, J. Chim. Phys., 1981, 78, 99. [all data]

Kimura, Katsumata, et al., 1981
Kimura, K.; Katsumata, S.; Achiba, Y.; Yamazaki, T.; Iwata, S., Ionization energies, Ab initio assignments, and valence electronic structure for 200 molecules in Handbook of HeI Photoelectron Spectra of Fundamental Organic Compounds, Japan Scientific Soc. Press, Tokyo, 1981. [all data]

Dannacher, Flamme, et al., 1980
Dannacher, J.; Flamme, J.P.; Stadelmann, J.P.; Vogt, J., Unimolecular fragmentations of internal energy selected 1,3-butadiene cations, Chem. Phys., 1980, 51, 189. [all data]

Bieri and Asbrink, 1980
Bieri, G.; Asbrink, L., 30.4-nm He(II) photoelectron spectra of organic molecules, J. Electron Spectrosc. Relat. Phenom., 1980, 20, 149. [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]

McDiarmid, 1976
McDiarmid, R., On the ultraviolet spectrum of trans-1,3-butadiene, J. Chem. Phys., 1976, 64, 514. [all data]

Brundle and Robin, 1970
Brundle, C.R.; Robin, M.B., Nonplanarity in hexafluorobutadiene as revealed by photoelectron and optical spectroscopy, J. Am. Chem. Soc., 1970, 92, 5550. [all data]

Matthews and Warneck, 1969
Matthews, C.S.; Warneck, P., Heats of formation of CHO+ and C3H3+ by photoionization, J. Chem. Phys. 5, 1969, 1, 854. [all data]

Eland, 1969
Eland, J.H.D., Photoelectron spectra of conjugated hydrocarbons and heteromolecules, Intern. J. Mass Spectrom. Ion Phys., 1969, 2, 471. [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]

Dewar and Worley, 1968
Dewar, M.J.S.; Worley, S.D., Ionization potential of cis-1,3-butadiene, J. Chem. Phys., 1968, 49, 2454. [all data]

Bock and Seidl, 1968
Bock, H.; Seidl, H., 'd-Orbital effects' in silicon- substituted π-electron systems. XI. Syntheses and properties of the isomeric bis(trimethylsilyl)-1,3-butadienes, J. Am. Chem. Soc., 1968, 90, 5694. [all data]

Franklin and Mogenis, 1967
Franklin, J.L.; Mogenis, A., An electron impact study of ions from several dienes, J. Phys. Chem., 1967, 71, 2820. [all data]

Brehm, 1966
Brehm, B., Massenspektrometrische Untersuchung der Photoionisation von Molekulen, Z. Naturforsch., 1966, 21a, 196. [all data]

Watanabe, 1954
Watanabe, K., Photoionization and total absorption cross section of gases. I. Ionization potentials of several molecules. Cross sections of NH3 and NO, J. Chem. Phys., 1954, 22, 1564. [all data]

Price and Walsh, 1940
Price, W.C.; Walsh, A.D., The absorption spectra of conjugated dienes in the vacuum ultra-violet (1), Proc. Roy. Soc. (London), 1940, A174, 220. [all data]

Schmidt, Schweig, et al., 1976
Schmidt, H.; Schweig, A.; Anastassiou, A.G.; Wetzel, J.C., The dominant role of hyperconjugation in the 9-oxabicyclo[4.2.1]nona-2,4,7-triene series, Tetrahedron, 1976, 32, 2239. [all data]

Field, Franklin, et al., 1957
Field, F.H.; Franklin, J.L.; Lampe, F.W., Reactions of gaseous ions. II. Acetylene, J. Am. Chem. Soc., 1957, 79, 2665. [all data]

Devisser, Dekoning, et al., 1995
Devisser, S.P.; Dekoning, L.J.; Vanderhart, W.J.; Nibbering, N.M.M., Chemical properties of butadienyl anions in the gas-phase, Recl. Trav. Chim. Pays-Bas, 1995, 114, 6, 267, https://doi.org/10.1002/recl.19951140603 . [all data]

Aflalaye, Sternberg, et al., 1995
Aflalaye, A.; Sternberg, R.; Raulin, F.; Vidal-Madjar, C., Gas chromatography of Titan's atmosphere. VI. Analysis of low-molecular-mass hydrocarbons and nitriles with BPX5 capillary columns, J. Chromatogr. A, 1995, 708, 2, 283-291, https://doi.org/10.1016/0021-9673(95)00410-O . [all data]

Do and Raulin, 1992
Do, L.; Raulin, F., Gas chromatography of Titan's atmosphere. III. Analysis of low-molecular-weight hydrocarbons and nitriles with a CP-Sil-5 CB WCOT capillary column, J. Chromatogr., 1992, 591, 1-2, 297-301, https://doi.org/10.1016/0021-9673(92)80247-R . [all data]

Bredael, 1982
Bredael, P., Retention indices of hydrocarbons on SE-30, J. Hi. Res. Chromatogr. Chromatogr. Comm., 1982, 5, 6, 325-328, https://doi.org/10.1002/jhrc.1240050610 . [all data]

Schröder, 1980
Schröder, I.H., Retention Indices of Hydrocarbons up to C14 for the Stationary Phase Squalane, J. Hi. Res. Chromatogr. Chromatogr. Comm., 1980, 3, 1, 38-44, https://doi.org/10.1002/jhrc.1240030115 . [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]

Hoekman, 1993
Hoekman, S.K., Improved gas chromatography procedure for speciated hydrocarbon measurements of vehicle emissions, J. Chromatogr., 1993, 639, 2, 239-253, https://doi.org/10.1016/0021-9673(93)80260-F . [all data]

White, Hackett, et al., 1992
White, C.M.; Hackett, J.; Anderson, R.R.; Kail, S.; Spock, P.S., Linear temperature programmed retention indices of gasoline range hydrocarbons and chlorinated hydrocarbons on cross-linked polydimethylsiloxane, J. Hi. Res. Chromatogr., 1992, 15, 2, 105-120, https://doi.org/10.1002/jhrc.1240150211 . [all data]

Fischer and Kusch, 1990
Fischer, W.G.; Kusch, P., Automatic sampler for Curie-point pyrolysis-gas chromatography with on-column introduction of pyrolysates, J. Chromatogr., 1990, 518, 9-19, https://doi.org/10.1016/S0021-9673(01)93158-9 . [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]

Schomburg, 1966
Schomburg, G., Gaschromatographische Retentionsdaten und Struktur Chemischer Verbindungen. II. Methylverzweigungen und Doppelbindungen in Offenkettigen Kohlenwasserstoffen, J. Chromatogr., 1966, 23, 1-17, https://doi.org/10.1016/S0021-9673(01)98652-2 . [all data]

Huguet, 1961
Huguet, M., Kovats retention indices in the qualitative analysis of light hydrocarbons by gas chromatography, Journees internationales d'etude des methodes de separation immediate et de chromatographie, 1961, 69. [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]

Tsuge, Ohtan, et al., 2011
Tsuge, S.; Ohtan, H.; Watanabe, C., Pyrolysis - GC/MS Data Book of Synthetic Polymers, Elsevier, 2011, 420. [all data]

Zenkevich, 2005
Zenkevich, I.G., Experimentally measured retention indices., 2005. [all data]

Chupalov and Zenkevich, 1996
Chupalov, A.A.; Zenkevich, I.G., Chromatographic Characterization of Structural Transformations of Organic Compounds in Diels-Alder Reaction. Aliphatic Dienes and Dienophyls, Zh. Org. Khim., 1996, 32, 6, 675-684. [all data]

Blunden, Aneja, et al., 2005
Blunden, J.; Aneja, V.P.; Lonneman, W.A., Characterization of non-methane volatile organic compounds at swine facilities in eastern North Carolina, Atm. Environ., 2005, 39, 36, 6707-6718, https://doi.org/10.1016/j.atmosenv.2005.03.053 . [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]

Zenkevich, 1998
Zenkevich, I.G., Application of Methods of Molecular Dynamics in Chromato-Spectral Identification of ISomeric Products of Organic reactions (in Russian), Zh. Org. Khim., 1998, 34, 10, 1463-1470. [all data]

Flanagan, Streete, et al., 1997
Flanagan, R.J.; Streete, P.J.; Ramsey, J.D., Volatile Substance Abuse, UNODC Technical Series, No 5, United Nations, Office on Drugs and Crime, Vienna International Centre, PO Box 500, A-1400 Vienna, Austria, 1997, 56, retrieved from http://www.odccp.org/pdf/technicalseries1997-01-011.pdf. [all data]

Robinson and Odell, 1971
Robinson, P.G.; Odell, A.L., A system of standard retention indices and its uses. The characterisation of stationary phases and the prediction of retention indices, J. Chromatogr., 1971, 57, 1-10, https://doi.org/10.1016/0021-9673(71)80001-8 . [all data]


Notes

Go To: Top, Gas phase ion energetics data, Mass spectrum (electron ionization), Gas Chromatography, References