1-Butene, 2,3-dimethyl-

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Gas 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
Δfgas-65.9 ± 1.5kJ/molCcbWiberg and Hao, 1991 
Δfgas-61. ± 2.kJ/molEqkRodgers and Wu, 1971Heat of isomerization

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
Δfliquid-95.1 ± 1.5kJ/molCcbWiberg and Hao, 1991 

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

Quantity Value Units Method Reference Comment
Tboil329.0 ± 0.6KAVGN/AAverage of 19 values; Individual data points
Quantity Value Units Method Reference Comment
Tfus120. ± 20.KAVGN/AAverage of 8 values; Individual data points
Quantity Value Units Method Reference Comment
Δvap29.2kJ/molN/AReid, 1972AC
Δvap29.2kJ/molVCamin and Rossini, 1956ALS
Δvap29.2kJ/molN/ACamin and Rossini, 1956, 2Based on data from 289. to 329. K.; AC

Enthalpy of vaporization

ΔvapH (kJ/mol) Temperature (K) Method Reference Comment
30.5282.AStephenson and Malanowski, 1987Based on data from 267. to 335. K.; AC

In addition to the Thermodynamics Research Center (TRC) data available from this site, much more physical and chemical property data is available from the following TRC products:


Reaction thermochemistry data

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change 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 by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

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

2-Butene, 2,3-dimethyl- = 1-Butene, 2,3-dimethyl-

By formula: C6H12 = C6H12

Quantity Value Units Method Reference Comment
Δr7.61 ± 0.50kJ/molEqkRadyuk, Kabo, et al., 1972gas phase; At 562 K
Δr7.1 ± 0.8kJ/molEqkRodgers and Wu, 1971gas phase; Heat of isomerization

Hydrogen + 1-Butene, 2,3-dimethyl- = Butane, 2,3-dimethyl-

By formula: H2 + C6H12 = C6H14

Quantity Value Units Method Reference Comment
Δr-116.3 ± 0.58kJ/molChydRogers, Crooks, et al., 1987liquid phase
Δr-116.1 ± 0.4kJ/molChydKistiakowsky, Ruhoff, et al., 1936gas phase

1-Butene, 2,3-dimethyl- = 2-Butene, 2,3-dimethyl-

By formula: C6H12 = C6H12

Quantity Value Units Method Reference Comment
Δr-7.1 ± 0.8kJ/molEqkRodgers and Wu, 1971gas phase; Heat of isomerization
Δr-7.5kJ/molEqkAbell, 1966gas phase

1-Butene, 2,3-dimethyl- + Hydrogen chloride = Butane, 2-chloro-2,3-dimethyl-

By formula: C6H12 + HCl = C6H13Cl

Quantity Value Units Method Reference Comment
Δr-62.2 ± 1.7kJ/molCmArnett and Pienta, 1980liquid phase; solvent: Methylene chloride; Hydrochlorination

1-Hexene = 1-Butene, 2,3-dimethyl-

By formula: C6H12 = C6H12

Quantity Value Units Method Reference Comment
Δr-23.2 ± 1.4kJ/molCisoBartolo and Rossini, 1960liquid phase; Calculated from ΔHc

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:
L - Sharon G. Lias

Data compiled as indicated in comments:
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi

View reactions leading to C6H12+ (ion structure unspecified)

Quantity Value Units Method Reference Comment
IE (evaluated)9.07 ± 0.01eVN/AN/AL

Ionization energy determinations

IE (eV) Method Reference Comment
9.07 ± 0.02PEBieri, Burger, et al., 1977LLK
9.072 ± 0.005PEMasclet, Grosjean, et al., 1973LLK
8.41PEBock and Kaim, 1980Vertical value; LLK

References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change 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.

Wiberg and Hao, 1991
Wiberg, K.B.; Hao, S., Enthalpies of hydration of alkenes. 4. Formation of acyclic tert-alcohols, J. Org. Chem., 1991, 56, 5108-5110. [all data]

Rodgers and Wu, 1971
Rodgers, A.S.; Wu, M.-C.R., Thermochemistry of the gas-phase iodine catalyzed isomerization: 2,3-dimethyl-1-butene = 2,3-dimethyl-2-butene, J. Chem. Thermodyn., 1971, 3, 591-597. [all data]

Reid, 1972
Reid, Robert C., Handbook on vapor pressure and heats of vaporization of hydrocarbons and related compounds, R. C. Wilhort and B. J. Zwolinski, Texas A Research Foundation. College Station, Texas(1971). 329 pages.$10.00, AIChE J., 1972, 18, 6, 1278-1278, https://doi.org/10.1002/aic.690180637 . [all data]

Camin and Rossini, 1956
Camin, D.L.; Rossini, F.D., Physical properties of the 17 isomeric hexenes of the API research series, J. Phys. Chem., 1956, 60, 1446. [all data]

Camin and Rossini, 1956, 2
Camin, David L.; Rossini, Frederick D., Physical Properties of the 17 Isomeric Hexenes.of the API Research Series, J. Phys. Chem., 1956, 60, 10, 1446-1451, https://doi.org/10.1021/j150544a029 . [all data]

Stephenson and Malanowski, 1987
Stephenson, Richard M.; Malanowski, Stanislaw, Handbook of the Thermodynamics of Organic Compounds, 1987, https://doi.org/10.1007/978-94-009-3173-2 . [all data]

Radyuk, Kabo, et al., 1972
Radyuk, Z.A.; Kabo, G.Ya.; Andreevskii, D.N., Equilibrium and thermodynamics of the isomerization of hexene isomers, Neftekhimiya, 1972, 12, 679-686. [all data]

Rogers, Crooks, et al., 1987
Rogers, D.W.; Crooks, E.; Dejroongruang, K., Enthalpies of hydrogenation of the hexenes, J. Chem. Thermodyn., 1987, 19, 1209-1215. [all data]

Kistiakowsky, Ruhoff, et al., 1936
Kistiakowsky, G.B.; Ruhoff, J.R.; Smith, H.A.; Vaughan, W.E., Heats of organic reactions. III. Hydrogenation of some higher olefins, J. Am. Chem. Soc., 1936, 58, 137-145. [all data]

Abell, 1966
Abell, P.I., Bromine atom catalyzed isomerization of terminal olefins, J. Am. Chem. Soc., 1966, 88, 1346-1348. [all data]

Arnett and Pienta, 1980
Arnett, E.M.; Pienta, N.J., Stabilities of carbonium ions in solution. 12. Heats of formation of alkyl chlorides as an entree to heats of solvation of aliphatic carbonium ions, J. Am. Chem. Soc., 1980, 102, 3329-3334. [all data]

Bartolo and Rossini, 1960
Bartolo, H.F.; Rossini, F.D., Heats of isomerization of the seventeen isomeric hexenes, J. Phys. Chem., 1960, 64, 1685-1689. [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]

Masclet, Grosjean, et al., 1973
Masclet, P.; Grosjean, D.; Mouvier, G., Alkene ionization potentials. Part I. Quantitative determination of alkyl group structural effects, J. Electron Spectrosc. Relat. Phenom., 1973, 2, 225. [all data]

Bock and Kaim, 1980
Bock, H.; Kaim, W., Radical ions. 37. Ionization and one-electron oxidation of electron-rich silylalkyl olefins, J. Am. Chem. Soc., 1980, 102, 4429. [all data]


Notes

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