1,3-Butadiene
- Formula: C4H6
- Molecular weight: 54.0904
- IUPAC Standard InChIKey: KAKZBPTYRLMSJV-UHFFFAOYSA-N
- CAS Registry Number: 106-99-0
- 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: α,γ-Butadiene; Biethylene; Bivinyl; Buta-1,3-diene; Butadiene; Divinyl; Erythrene; Pyrrolylene; Vinylethylene; CH2=CHCH=CH2; Butadieen; Buta-1,3-dieen; Butadien; Buta-1,3-dien; NCI-C50602
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Condensed phase thermochemistry data
Go To: Top, Reaction thermochemistry data, Gas phase ion energetics 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 as indicated in comments:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DH - Eugene S. Domalski and Elizabeth D. Hearing
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°liquid | 21.63 ± 0.23 | kcal/mol | Ccb | Prosen and Rossini, 1945 | ALS |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°liquid | -602.79 ± 0.23 | kcal/mol | Ccb | Prosen and Rossini, 1945 | Corresponding ΔfHºliquid = 21.64 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS |
Quantity | Value | Units | Method | Reference | Comment |
S°liquid | 47.562 | cal/mol*K | N/A | Scott, Meyers, et al., 1945 | At vapor pressure of 2105 Torr.; DH |
Constant pressure heat capacity of liquid
Cp,liquid (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
29.553 | 298.15 | Scott, Meyers, et al., 1945 | T = 15 to 303 K.; DH |
Reaction thermochemistry data
Go To: Top, Condensed phase thermochemistry data, Gas phase ion energetics 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 as indicated in comments:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
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
By formula: C4H6 + 2H2 = C4H10
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -56.57 ± 0.10 | kcal/mol | Chyd | Kistiakowsky, Ruhoff, et al., 1936 | gas phase; Reanalyzed by Cox and Pilcher, 1970, Original value = -57.1 ± 0.1 kcal/mol; At 355 °K; ALS |
C4H5- + =
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 399.5 ± 3.1 | kcal/mol | G+TS | Devisser, Dekoning, et al., 1995 | gas phase; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 391.3 ± 3.0 | kcal/mol | IMRB | Devisser, Dekoning, et al., 1995 | gas phase; B |
By formula: Na+ + C4H6 = (Na+ • C4H6)
Free energy of reaction
ΔrG° (kcal/mol) | T (K) | Method | Reference | Comment |
---|---|---|---|---|
10.3 | 298. | IMRE | McMahon and Ohanessian, 2000 | Anchor alanine=39.89; RCD |
(CAS Reg. No. 88032-19-3 • 4294967295) +
= CAS Reg. No. 88032-19-3
By formula: (CAS Reg. No. 88032-19-3 • 4294967295C4H6) + C4H6 = CAS Reg. No. 88032-19-3
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 14.7 ± 2.1 | kcal/mol | N/A | DePuy, Gronert, et al., 1989 | gas phase; B |
By formula: C8H8O3 = C4H6 + C4H2O3
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 67.79 ± 0.23 | kcal/mol | Cm | Ghitau, Ciopec, et al., 1983 | solid phase; At 65 to 90°C; ALS |
By formula: C4H6 + O2S = C4H6O2S
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -17.9 | kcal/mol | Eqk | Mackle and McNally, 1969 | gas phase; ALS |
By formula: C4H6 + C4H2O3 = C8H8O3
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -67.788 | kcal/mol | Cm | Ghitau, Ciopec, et al., 1983 | liquid phase; ALS |
By formula: C4H6 + O2S = C4H6O2S
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -16.5 | kcal/mol | Eqk | Mackle and McNally, 1969 | gas phase; ALS |
By formula: C4H6 = C4H6
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 12.78 ± 0.16 | kcal/mol | Ccb | Prosen, Maron, et al., 1949 | gas phase; ALS |
By formula: Au+ + C4H6 = (Au+ • C4H6)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | >75. | kcal/mol | IMRB | Schroeder, Hrusak, et al., 1995 | RCD |
Gas phase ion energetics data
Go To: Top, Condensed phase thermochemistry data, Reaction thermochemistry data, 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 ± 0.007 | eV | N/A | N/A | L |
Quantity | Value | Units | Method | Reference | Comment |
Proton affinity (review) | 187.2 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
Quantity | Value | Units | Method | Reference | Comment |
Gas basicity | 181.1 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
9.082 ± 0.004 | S | Mallard, Miller, et al., 1983 | LBLHLM |
9.07 | PE | Masclet, Mouvier, et al., 1981 | LLK |
9.09 | PE | Kimura, Katsumata, et al., 1981 | LLK |
9.03 | EI | Dannacher, Flamme, et al., 1980 | LLK |
9.03 | PE | Bieri and Asbrink, 1980 | LLK |
9.03 ± 0.02 | PE | Bieri, Burger, et al., 1977 | LLK |
9.0691 | S | McDiarmid, 1976 | LLK |
9.06 | PE | Brundle and Robin, 1970 | RDSH |
9.06 ± 0.02 | PI | Matthews and Warneck, 1969 | RDSH |
9.09 ± 0.05 | PE | Eland, 1969 | RDSH |
9.07 ± 0.02 | PI | Parr and Elder, 1968 | RDSH |
9.07 | PE | Dewar and Worley, 1968 | RDSH |
~9.2 | DER | Dewar and Worley, 1968 | RDSH |
9.18 ± 0.04 | EI | Bock and Seidl, 1968 | RDSH |
9.09 ± 0.03 | EI | Franklin and Mogenis, 1967 | RDSH |
9.075 ± 0.005 | PI | Brehm, 1966 | RDSH |
9.07 ± 0.01 | PI | Watanabe, 1954 | RDSH |
9.06 ± 0.01 | S | Price and Walsh, 1940 | RDSH |
9.03 | PE | Schmidt, Schweig, et al., 1976 | Vertical value; LLK |
Appearance energy determinations
De-protonation reactions
C4H5- + =
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 399.5 ± 3.1 | kcal/mol | G+TS | Devisser, Dekoning, et al., 1995 | gas phase; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 391.3 ± 3.0 | kcal/mol | IMRB | Devisser, Dekoning, et al., 1995 | gas phase; B |
References
Go To: Top, Condensed phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Prosen and Rossini, 1945
Prosen, E.J.; Rossini, F.D.,
Heats of formation and combustion of 1,3-butadiene and styrene,
J. Res. NBS, 1945, 34, 59-63. [all data]
Scott, Meyers, et al., 1945
Scott, R.B.; Meyers, C.H.; Rands, R.D., Jr.; Brickwedde, F.G.; Bekkedahl, N.,
Thermodynamic properties of 1,3-butadiene in the solid, liquid, and vapor states,
J. Res. NBS, 1945, 35, 39-85. [all data]
Kistiakowsky, Ruhoff, et al., 1936
Kistiakowsky, G.B.; Ruhoff, J.R.; Smith, H.A.; Vaughan, W.E.,
Heats of organic reactions. IV. Hydrogenation of some dienes and of benzene,
J. Am. Chem. Soc., 1936, 58, 146-153. [all data]
Cox and Pilcher, 1970
Cox, J.D.; Pilcher, G.,
Thermochemistry of Organic and Organometallic Compounds, Academic Press, New York, 1970, 1-636. [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]
McMahon and Ohanessian, 2000
McMahon, T.B.; Ohanessian, G.,
An Experimental and Ab Initio Study of the Nature of the Binding in Gas-Phase Complexes of Sodium Ions,
Chem. Eur. J., 2000, 6, 16, 2931, https://doi.org/10.1002/1521-3765(20000818)6:16<2931::AID-CHEM2931>3.0.CO;2-7
. [all data]
DePuy, Gronert, et al., 1989
DePuy, C.H.; Gronert, S.; Barlow, S.E.; Bierbaum, V.M.; Damrauer, R.,
The Gas Phase Acidities of the Alkanes,
J. Am. Chem. Soc., 1989, 111, 6, 1968, https://doi.org/10.1021/ja00188a003
. [all data]
Ghitau, Ciopec, et al., 1983
Ghitau, M.; Ciopec, M.; Pintea, O.,
Study on Diels-Alder reaction for the synthesis of tetrahydrophthalic anhydride,
Rev. Chim. (Bucharest), 1983, 34, 299-305. [all data]
Mackle and McNally, 1969
Mackle, H.; McNally, D.V.,
Studies in the thermochemistry of sulphones. Part 9 - Thermochemistry of the butadiene and isoprene sulphones,
Trans. Faraday Soc., 1969, 65, 1738-1741. [all data]
Prosen, Maron, et al., 1949
Prosen, E.J.; Maron, F.W.; Rossini, F.D.,
Heat of isomerization of the two butadienes,
J. Res. NBS, 1949, 42, 269-275. [all data]
Schroeder, Hrusak, et al., 1995
Schroeder, D.; Hrusak, J.; Hertwig, R.H.; Koch, W.; Schwerdtfeger, P.; Schwarz, H.,
Experimental and Theoretical Studies of Gold(I) Complexes Au(L)+ (L=H2O, CO, NH3, C2H4, C3H6, C4H6, C6H6, C6F6),
Organometallics, 1995, 14, 1, 312, https://doi.org/10.1021/om00001a045
. [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]
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]
Notes
Go To: Top, Condensed phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, References
- Symbols used in this document:
AE Appearance energy Cp,liquid Constant pressure heat capacity of liquid IE (evaluated) Recommended ionization energy S°liquid Entropy of liquid at standard conditions T Temperature ΔcH°liquid Enthalpy of combustion of liquid 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 - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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