1-Butene, 2,3-dimethyl-
- Formula: C6H12
- Molecular weight: 84.1595
- IUPAC Standard InChIKey: OWWIWYDDISJUMY-UHFFFAOYSA-N
- CAS Registry Number: 563-78-0
- 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. - Species with the same structure:
- Other names: 2,3-Dimethyl-1-butene; (CH3)2CHC(CH3)=CH2; 2,3-Dimethylbutene-1; 2,3-dimethylbut-1-ene
- Information on this page:
- Other data available:
- Data at other public NIST sites:
- Options:
Data at NIST subscription sites:
NIST subscription sites provide data under the NIST Standard Reference Data Program, but require an annual fee to access. The purpose of the fee is to recover costs associated with the development of data collections included in such sites. Your institution may already be a subscriber. Follow the links above to find out more about the data in these sites and their terms of usage.
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 by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°liquid | -22.73 ± 0.35 | kcal/mol | Ccb | Wiberg and Hao, 1991 |
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 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
By formula: C6H12 = C6H12
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 1.82 ± 0.12 | kcal/mol | Eqk | Radyuk, Kabo, et al., 1972 | gas phase; At 562 K |
ΔrH° | 1.7 ± 0.2 | kcal/mol | Eqk | Rodgers and Wu, 1971 | gas phase; Heat of isomerization |
By formula: H2 + C6H12 = C6H14
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -27.80 ± 0.14 | kcal/mol | Chyd | Rogers, Crooks, et al., 1987 | liquid phase |
ΔrH° | -27.8 ± 0.1 | kcal/mol | Chyd | Kistiakowsky, Ruhoff, et al., 1936 | gas phase |
By formula: C6H12 = C6H12
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -1.7 ± 0.2 | kcal/mol | Eqk | Rodgers and Wu, 1971 | gas phase; Heat of isomerization |
ΔrH° | -1.8 | kcal/mol | Eqk | Abell, 1966 | gas phase |
By formula: C6H12 + HCl = C6H13Cl
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -14.86 ± 0.41 | kcal/mol | Cm | Arnett and Pienta, 1980 | liquid phase; solvent: Methylene chloride; Hydrochlorination |
By formula: C6H12 = C6H12
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -5.55 ± 0.34 | kcal/mol | Ciso | Bartolo and Rossini, 1960 | liquid phase; Calculated from ΔHc |
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:
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 ± 0.01 | eV | N/A | N/A | L |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
9.07 ± 0.02 | PE | Bieri, Burger, et al., 1977 | LLK |
9.072 ± 0.005 | PE | Masclet, Grosjean, et al., 1973 | LLK |
8.41 | PE | Bock and Kaim, 1980 | Vertical value; LLK |
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.
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]
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]
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]
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
Go To: Top, Condensed phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, References
- Symbols used in this document:
IE (evaluated) Recommended ionization energy ΔfH°liquid Enthalpy of formation of liquid at standard conditions ΔrH° Enthalpy of reaction at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
- The National Institute of Standards and Technology (NIST) uses its best efforts to deliver a high quality copy of the Database and to verify that the data contained therein have been selected on the basis of sound scientific judgment. However, NIST makes no warranties to that effect, and NIST shall not be liable for any damage that may result from errors or omissions in the Database.
- Customer support for NIST Standard Reference Data products.