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2-Methyl-1-butene

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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
Deltafgas-8.39 ± 0.20kcal/molEqkWiberg and Hao, 1991Heat of hydration; ALS
Deltafgas-8.32kcal/molN/AGood and Smith, 1979Value computed using «DELTA»fHliquid° value of -60.96±0.84 kj/mol from Good and Smith, 1979 and «DELTA»vapH° value of 26.19 kj/mol from missing citation.; DRB

Constant pressure heat capacity of gas

Cp,gas (cal/mol*K) Temperature (K) Reference Comment
24.610273.15McCullough J.P., 1959Results of more recent statistical calculation [ Durig J.R., 1980] are different from recommended and experimental values up to 3 J/mol*K for S(T) and Cp(T).; GT
26.281298.15
26.410300.
33.200400.
39.400500.
44.720600.
49.259700.
53.150800.
56.520900.
59.4311000.
61.9601100.
64.1491200.
66.0491300.
67.7101400.
69.1491500.

Constant pressure heat capacity of gas

Cp,gas (cal/mol*K) Temperature (K) Reference Comment
27.761 ± 0.084320.66Scott D.W., 1949GT
30.681 ± 0.093362.51
33.61 ± 0.10407.11
36.60 ± 0.11453.41
39.52 ± 0.12502.21

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 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
Deltafliquid-14.57 ± 0.20kcal/molCcbGood and Smith, 1979ALS
Quantity Value Units Method Reference Comment
Deltacliquid-797.26 ± 0.19kcal/molCcbGood and Smith, 1979Corresponding «DELTA»fliquid = -14.57 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS
Quantity Value Units Method Reference Comment
liquid60.71cal/mol*KN/AChao, Hall, et al., 1983DH
liquid60.700cal/mol*KN/ATodd, Oliver, et al., 1947DH

Constant pressure heat capacity of liquid

Cp,liquid (cal/mol*K) Temperature (K) Reference Comment
37.60298.15Chao, Hall, et al., 1983T = 12 to 293 K.; DH
37.569298.15Todd, Oliver, et al., 1947T = 12 to 300 K.; DH

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 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

Hydrogen + 2-Methyl-1-butene = Butane, 2-methyl-

By formula: H2 + C5H10 = C5H12

Quantity Value Units Method Reference Comment
Deltar-30.341kcal/molChydDolliver, Gresham, et al., 1937gas phase; At 355 °K
Deltar-28.25 ± 0.10kcal/molChydKistiakowsky, Ruhoff, et al., 1936gas phase; Reanalyzed by Cox and Pilcher, 1970, Original value = -28.49 ± 0.36 kcal/mol; At 355 K

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

By formula: C5H10 + CH4O = C6H14O

Quantity Value Units Method Reference Comment
Deltar-8.56kcal/molEqkSerda, Izquierdo, et al., 1995liquid phase
Deltar-4.9 ± 0.2kcal/molEqkHwang and Wu, 1994liquid phase
Deltar-8.0 ± 1.2kcal/molEqkRihko, Linnekoski, et al., 1994liquid phase; solvent: Alcohol/alkane mixture

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

By formula: C5H10 = C5H10

Quantity Value Units Method Reference Comment
Deltar-1.6 ± 0.72kcal/molEqkRihko, Linnekoski, et al., 1994liquid phase; solvent: Methanol/H+
Deltar-1.9 ± 0.33kcal/molEqkRihko, Linnekoski, et al., 1994liquid phase; solvent: Ethanol/H+

2-Methyl-1-butene + Hydrogen chloride = Butane, 2-chloro-2-methyl-

By formula: C5H10 + HCl = C5H11Cl

Quantity Value Units Method Reference Comment
Deltar-15.23 ± 0.34kcal/molCmArnett and Pienta, 1980liquid phase; solvent: Methylene chloride; Hydrochlorination

2-Methyl-1-butene + Ethanol = Butane, 2-ethoxy-2-methyl-

By formula: C5H10 + C2H6O = C7H16O

Quantity Value Units Method Reference Comment
Deltar-8.4 ± 1.4kcal/molEqkRihko, Linnekoski, et al., 1994liquid phase; solvent: Alcohol/alkane mixture

2-Methyl-1-butene + Trifluoroacetic acid = Acetic acid, trifluoro-, 2,2-dimethylpropyl ester

By formula: C5H10 + C2HF3O2 = C7H11F3O2

Quantity Value Units Method Reference Comment
Deltar-10.93 ± 0.04kcal/molCmWiberg and Hao, 1991liquid phase; Trifuoroacetolysis

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

By formula: C5H10 = C5H10

Quantity Value Units Method Reference Comment
Deltar1.93 ± 0.12kcal/molEqkRadyuk, Kabo, et al., 1973gas phase; Heat of isomerization at 562 K

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

By formula: C5H10 + CH4O = C6H14O

Quantity Value Units Method Reference Comment
Deltar-8.56 ± 0.31kcal/molEqkSerda, Izquierdo, et al., 1995liquid phase

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

By formula: C6H14O = C5H10 + CH4O

Quantity Value Units Method Reference Comment
Deltar16.24 ± 0.093kcal/molEqkRozhnov, Safronov, et al., 1991liquid phase

References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Reaction thermochemistry 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]

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]

McCullough J.P., 1959
McCullough J.P., Thermodynamic properties, vibrational assignment and rotational conformations of 2-methyl-1-butene, J. Am. Chem. Soc., 1959, 81, 1331-1334. [all data]

Durig J.R., 1980
Durig J.R., Torsional spectra of molecules with two internal C3v rotors. 19. Vibrational spectra, torsional potential functions, and conformational and thermodynamic properties of 2-methyl-1-butene, J. Phys. Chem., 1980, 84, 3554-3561. [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]

Chao, Hall, et al., 1983
Chao, J.; Hall, K.R.; Yao, J.M., Thermodynamic properties of simple alkenes, Thermochim. Acta, 1983, 64(3), 285-303. [all data]

Todd, Oliver, et al., 1947
Todd, S.S.; Oliver, G.D.; Huffman, H.M., The heat capacities, heats of fusion and entropies of the six pentenes, J. Am. Chem. Soc., 1947, 69, 1519-1525. [all data]

Dolliver, Gresham, et al., 1937
Dolliver, M.a.; Gresham, T.L.; Kistiakowsky, G.B.; Vaughan, W.E., Heats of organic reactions. V. Heats of hydrogenation of various hydrocarbons, J. Am. Chem. Soc., 1937, 59, 831-841. [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]

Cox and Pilcher, 1970
Cox, J.D.; Pilcher, G., Thermochemistry of Organic and Organometallic Compounds, Academic Press, New York, 1970, 1-636. [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]

Hwang and Wu, 1994
Hwang, W.-S.; Wu, J.-C., Kinetics and thermodynamics of synthesis of tertiary-amyl methyl ether catalyzed by ion-exchange resin, J. Chin. Chem. Soc. (Taipei), 1994, 41, 181-186. [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]

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]

Rozhnov, Safronov, et al., 1991
Rozhnov, A.M.; Safronov, V.V.; Verevkin, S.P.; Sharonov, K.G.; Alenin, V.I., Enthalpy of combustion and enthalpy of vaporization of 2-ethyl-2-methoxypropane and thermodynamics of its gas-phase synthesis from (methanol + a 2-methylbutene), J. Chem. Thermodyn., 1991, 23, 629-635. [all data]


Notes

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