2-Butene, 2-methyl-

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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 as indicated in comments:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DRB - Donald R. Burgess, Jr.
GT - Glushko Thermocenter, Russian Academy of Sciences, Moscow

Quantity Value Units Method Reference Comment
Δfgas-41.5 ± 0.88kJ/molEqkWiberg and Hao, 1991Heat of hydration; ALS
Δfgas-41.0kJ/molN/AGood and Smith, 1979Value computed using ΔfHliquid° value of -68.1±1.3 kj/mol from Good and Smith, 1979 and ΔvapH° value of 27.1 kj/mol from Wiberg and Hao, 1991.; DRB

Constant pressure heat capacity of gas

Cp,gas (J/mol*K) Temperature (K) Reference Comment
111.00 ± 0.33319.04Scott D.W., 1949GT
122.97 ± 0.37362.37
133.93 ± 0.40402.26
143.05 ± 0.43436.18
152.05 ± 0.46471.09

Constant pressure heat capacity of gas

Cp,gas (J/mol*K) Temperature (K) Reference Comment
105.02298.15Scott D.W., 1949Recommended results of statistical thermodynamics calculation are in good agreement with experimental data.; GT
105.52300.
133.60400.
159.28500.
181.67600.
201.00700.
217.78800.
232.30900.
244.971000.
255.891100.
265.471200.
273.711300.
280.911400.
287.151500.

Reaction 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 as indicated in comments:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
M - Michael M. Meot-Ner (Mautner) and Sharon G. Lias

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-Methyl-1-butene = 2-Butene, 2-methyl-

By formula: C5H10 = C5H10

Quantity Value Units Method Reference Comment
Δr-6.7 ± 3.0kJ/molEqkRihko, Linnekoski, et al., 1994liquid phase; solvent: Methanol/H+; ALS
Δr-8.0 ± 1.4kJ/molEqkRihko, Linnekoski, et al., 1994liquid phase; solvent: Ethanol/H+; ALS

C3H9Si+ + 2-Butene, 2-methyl- = (C3H9Si+ • 2-Butene, 2-methyl-)

By formula: C3H9Si+ + C5H10 = (C3H9Si+ • C5H10)

Quantity Value Units Method Reference Comment
Δr160.kJ/molPHPMSLi and Stone, 1989gas phase; condesation; M
Quantity Value Units Method Reference Comment
Δr201.J/mol*KPHPMSLi and Stone, 1989gas phase; condesation; M

2-Butene, 2-methyl- + Methyl Alcohol = Butane, 2-methoxy-2-methyl-

By formula: C5H10 + CH4O = C6H14O

Quantity Value Units Method Reference Comment
Δr-32.8kJ/molEqkSerda, Izquierdo, et al., 1995liquid phase; ALS
Δr-26.8 ± 2.3kJ/molEqkRihko, Linnekoski, et al., 1994liquid phase; solvent: Alcohol/alkane mixture; ALS

2-Butene, 2-methyl- + Hydrogen chloride = Butane, 2-chloro-2-methyl-

By formula: C5H10 + HCl = C5H11Cl

Quantity Value Units Method Reference Comment
Δr-59.08 ± 0.92kJ/molCmArnett and Pienta, 1980liquid phase; solvent: Methylene chloride; Hydrochloroination; ALS

2-Butene, 2-methyl- + Ethanol = Butane, 2-ethoxy-2-methyl-

By formula: C5H10 + C2H6O = C7H16O

Quantity Value Units Method Reference Comment
Δr-27.3 ± 6.7kJ/molEqkRihko, Linnekoski, et al., 1994liquid phase; solvent: Alcohol/alkane mixture; ALS

2-Butene, 2-methyl- + Trifluoroacetic acid = Acetic acid, trifluoro-, 2,2-dimethylpropyl ester

By formula: C5H10 + C2HF3O2 = C7H11F3O2

Quantity Value Units Method Reference Comment
Δr-38.1 ± 0.2kJ/molCmWiberg and Hao, 1991liquid phase; Trifluoroacetolysis; ALS

2-Butene, 2-methyl- = 1-Butene, 3-methyl-

By formula: C5H10 = C5H10

Quantity Value Units Method Reference Comment
Δr14.2 ± 1.5kJ/molEqkRadyuk, Kabo, et al., 1973gas phase; Heat of isomerization at 622 K; ALS

2-Butene, 2-methyl- = 2-Methyl-1-butene

By formula: C5H10 = C5H10

Quantity Value Units Method Reference Comment
Δr8.08 ± 0.50kJ/molEqkRadyuk, Kabo, et al., 1973gas phase; Heat of isomerization at 562 K; ALS

2-Butene, 2-methyl- + Bromine = 2,3-dibromo-2-methylbutane

By formula: C5H10 + Br2 = C5H10Br2

Quantity Value Units Method Reference Comment
Δr-127.2 ± 0.84kJ/molCmConn, Kistiakowsky, et al., 1938gas phase; At 355 °K; ALS

Hydrogen + 2-Butene, 2-methyl- = Butane, 2-methyl-

By formula: H2 + C5H10 = C5H12

Quantity Value Units Method Reference Comment
Δr-111.6 ± 0.3kJ/molChydKistiakowsky, Ruhoff, et al., 1936gas phase; ALS

2-Butene, 2-methyl- + Methyl Alcohol = Butane, 1-methoxy-2-methyl-

By formula: C5H10 + CH4O = C6H14O

Quantity Value Units Method Reference Comment
Δr-32.8 ± 1.4kJ/molEqkSerda, Izquierdo, et al., 1995liquid phase; ALS

Butane, 2-ethoxy-2-methyl- = 2-Butene, 2-methyl- + Ethanol

By formula: C7H16O = C5H10 + C2H6O

Quantity Value Units Method Reference Comment
Δr34.13 ± 0.81kJ/molEqkSharonov, Rozhnov, et al., 1995liquid phase; ALS

Gas phase ion energetics data

Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry 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 evaluated as indicated in comments:
HL - Edward P. Hunter and Sharon G. Lias
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 C5H10+ (ion structure unspecified)

Quantity Value Units Method Reference Comment
IE (evaluated)8.69 ± 0.01eVN/AN/AL
Quantity Value Units Method Reference Comment
Proton affinity (review)808.8kJ/molN/AHunter and Lias, 1998HL
Quantity Value Units Method Reference Comment
Gas basicity779.9kJ/molN/AHunter and Lias, 1998HL

Ionization energy determinations

IE (eV) Method Reference Comment
8.69PITraeger, 1986LBLHLM
8.68 ± 0.02PEBieri, Burger, et al., 1977LLK
8.682 ± 0.003PEMasclet, Grosjean, et al., 1973LLK
8.70EILossing, 1972LLK
8.83 ± 0.11EIGross and Wilkins, 1971LLK
8.72PEFrost and Sandhu, 1971LLK
8.85 ± 0.04EIBock and Seidl, 1968RDSH
8.67 ± 0.02PIWatanabe, Nakayama, et al., 1962RDSH
8.68PIBralsford, Harris, et al., 1960RDSH

Appearance energy determinations

Ion AE (eV) Other Products MethodReferenceComment
C3H6+11.70 ± 0.11C2H4EIGross and Wilkins, 1971LLK
C4H7+10.80CH3PITraeger, 1986LBLHLM
C4H7+10.84CH3EIBrand and Baer, 1984LBLHLM
C4H7+10.84CH3EILossing, 1972LLK
C4H7+11.33 ± 0.12CH3EIGross and Wilkins, 1971LLK

Mass spectrum (electron ionization)

Go To: Top, Gas phase thermochemistry data, 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: NIST Mass Spectrometry Data Center, William E. Wallace, director

Spectrum

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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.
Origin Japan AIST/NIMC Database- Spectrum MS-NW-1329
NIST MS number 233774

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References

Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, Mass spectrum (electron ionization), 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]

Good and Smith, 1979
Good, W.D.; Smith, N.K., The enthalpies of combustion of the isomeric pentenes in the liquid state. A warning to combustion calorimetrists about sample drying, J. Chem. Thermodyn., 1979, 11, 111-118. [all data]

Scott D.W., 1949
Scott D.W., Thermodynamic properties of three isomeric pentenes, J. Am. Chem. Soc., 1949, 71, 2767-2773. [all data]

Rihko, Linnekoski, et al., 1994
Rihko, L.K.; Linnekoski, J.A.; Krause, A.O., Reaction equilibria in the synthesis of 2-methoxy-2-methylbutane and 2-ethyoxy-2-methylbutane in the liquid phase, J. Chem. Eng. Data, 1994, 39, 700-704. [all data]

Li and Stone, 1989
Li, X.; Stone, J.A., Determination of the beta silicon effect from a mass spectrometric study of the association of trimethylsilylium ion with alkenes, J. Am. Chem. Soc., 1989, 111, 15, 5586, https://doi.org/10.1021/ja00197a013 . [all data]

Serda, Izquierdo, et al., 1995
Serda, J.A.; Izquierdo, J.F.; Tejero, J.; Cunill, F.; Iborra, M., Equilibrium and thermodynamics for 2-methyl-2-methoxybutane liquid-phase decomposition, Thermochim. Acta, 1995, 259, 111-120. [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]

Radyuk, Kabo, et al., 1973
Radyuk, Z.A.; Kabo, G.Ya.; Andreevskii, D.N., Isomerization equilibrium and thermodynamic properties of methylbutenes, Neftekhimiya, 1973, 13, 356-360. [all data]

Conn, Kistiakowsky, et al., 1938
Conn, J.B.; Kistiakowsky, G.B.; Smith, E.A., Heats of organic reactions. VII. Addition of halogens to olefins, J. Am. Chem. Soc., 1938, 60, 2764-2771. [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]

Sharonov, Rozhnov, et al., 1995
Sharonov, K.G.; Rozhnov, A.M.; Korol'kov, A.V.; Karaseva, S.Y., Enthalpies of formation of 2-methyl-2-ethoxypropane and 2-ethyl-2-ethoxypropane from equilibrium measurements, J. Chem. Thermodyn., 1995, 27, 751-753. [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]

Traeger, 1986
Traeger, J.C., Heat of formation for the 1-methylallyl cation by photoionization mass spectrometry, J. Phys. Chem., 1986, 90, 4114. [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]

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, Can. J. Chem., 1972, 50, 3973. [all data]

Gross and Wilkins, 1971
Gross, M.L.; Wilkins, C.L., Computer-assisted ion cyclotron resonance appearance potential measurements for C5H10 isomers, Anal. Chem., 1971, 43, 1624. [all data]

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]

Bock and Seidl, 1968
Bock, H.; Seidl, H., d-Orbitaleffekte in siliziumsubstituierten π-Elektronensystemen. VI. Spektroskopische Untersuchungen an Alkyl- und Silylathylenen, J. Organometal. Chem., 1968, 13, 87. [all data]

Watanabe, Nakayama, et al., 1962
Watanabe, K.; Nakayama, T.; Mottl, J., Ionization potentials of some molecules, J. Quant. Spectry. Radiative Transfer, 1962, 2, 369. [all data]

Bralsford, Harris, et al., 1960
Bralsford, R.; Harris, P.V.; Price, W.C., The effect of fluorine on the electronic spectra and ionization potentials of molecules, Proc. Roy. Soc. (London), 1960, A258, 459. [all data]

Brand and Baer, 1984
Brand, W.A.; Baer, T., Dissociation dynamics of energy-selected C5H10+ ions, J. Am. Chem. Soc., 1984, 106, 3154. [all data]


Notes

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