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2-Butene, 2-methyl-

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Gas phase thermochemistry data

Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, IR Spectrum, 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 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-9.92 ± 0.21kcal/molEqkWiberg and Hao, 1991Heat of hydration; ALS
Deltafgas-9.80kcal/molN/AGood and Smith, 1979Value computed using «DELTA»fHliquid° value of -68.1±1.3 kj/mol from Good and Smith, 1979 and «DELTA»vapH° value of 27.1 kj/mol from Wiberg and Hao, 1991.; DRB

Constant pressure heat capacity of gas

Cp,gas (cal/mol*K) Temperature (K) Reference Comment
26.530 ± 0.079319.04Scott D.W., 1949GT
29.391 ± 0.088362.37
32.010 ± 0.096402.26
34.19 ± 0.10436.18
36.34 ± 0.11471.09

Constant pressure heat capacity of gas

Cp,gas (cal/mol*K) Temperature (K) Reference Comment
25.100298.15Scott D.W., 1949Recommended results of statistical thermodynamics calculation are in good agreement with experimental data.; GT
25.220300.
31.931400.
38.069500.
43.420600.
48.040700.
52.051800.
55.521900.
58.5491000.
61.1591100.
63.4491200.
65.4181300.
67.1391400.
68.6301500.

Condensed phase thermochemistry data

Go To: Top, Gas phase thermochemistry data, Phase change data, Reaction thermochemistry data, IR Spectrum, 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 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-16.4 ± 0.2kcal/molEqkWiberg and Hao, 1991Heat of hydration; ALS
Deltafliquid-16.27 ± 0.31kcal/molCcbGood and Smith, 1979ALS
Quantity Value Units Method Reference Comment
Deltacliquid-795.56 ± 0.30kcal/molCcbGood and Smith, 1979Corresponding «DELTA»fliquid = -16.27 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS
Quantity Value Units Method Reference Comment
liquid60.04cal/mol*KN/AChao, Hall, et al., 1983DH
liquid60.000cal/mol*KN/ATodd, Oliver, et al., 1947DH
liquid59.49cal/mol*KN/AParks and Huffman, 1930Extrapolation below 90 K, 13.12 cal/mol*K.; DH

Constant pressure heat capacity of liquid

Cp,liquid (cal/mol*K) Temperature (K) Reference Comment
36.52298.15Chao, Hall, et al., 1983T = 13 to 301 K.; DH
36.520298.15Todd, Oliver, et al., 1947T = 12 to 300 K.; DH
34.99293.9Parks and Huffman, 1930T = 93 to 294 K. Value is unsmoothed experimental datum.; DH

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
DH - Eugene S. Domalski and Elizabeth D. Hearing

Quantity Value Units Method Reference Comment
Tboil311. ± 1.KAVGN/AAverage of 44 out of 45 values; Individual data points
Quantity Value Units Method Reference Comment
Tfus140. ± 10.KAVGN/AAverage of 10 values; Individual data points
Quantity Value Units Method Reference Comment
Ttriple139.40KN/AChao, Hall, et al., 1983, 2Uncertainty assigned by TRC = 0.02 K; TRC
Ttriple139.42KN/ATodd, Oliver, et al., 1947, 2Uncertainty assigned by TRC = 0.05 K; TRC
Ttriple139.440KN/AHuffman, 1945Uncertainty assigned by TRC = 0.6 K; TRC
Ttriple139.420KN/AHuffman, 1945Uncertainty assigned by TRC = 0.6 K; TRC
Ttriple138.9KN/AParks and Huffman, 1930, 2Uncertainty assigned by TRC = 0.2 K; TRC
Quantity Value Units Method Reference Comment
Tc470. ± 1.KN/ATsonopoulos and Ambrose, 1996 
Tc481.KN/AMajer and Svoboda, 1985 
Quantity Value Units Method Reference Comment
Pc33.8 ± 0.99atmN/ATsonopoulos and Ambrose, 1996 
Quantity Value Units Method Reference Comment
Deltavap6.534kcal/molN/AMajer and Svoboda, 1985 
Deltavap6.48kcal/molN/AReid, 1972AC
Deltavap6.48 ± 0.02kcal/molCScott, Waddington, et al., 1949AC

Enthalpy of vaporization

DeltavapH (kcal/mol) Temperature (K) Method Reference Comment
6.288311.7N/AMajer and Svoboda, 1985 
6.79286.AStephenson and Malanowski, 1987Based on data from 271. - 343. K.; AC
6.76291.N/AScott, Waddington, et al., 1949Based on data from 276. - 344. K.; AC
6.57 ± 0.02290.CScott, Waddington, et al., 1949AC
6.29 ± 0.02312.CScott, Waddington, et al., 1949AC

Enthalpy of vaporization

ΔvapH = A exp(-βTr) (1 − Tr)β
    ΔvapH = Enthalpy of vaporization (at saturation pressure) (kcal/mol)
    Tr = reduced temperature (T / Tc)

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Temperature (K) A (kcal/mol) beta Tc (K) Reference Comment
290. - 312.9.9090.2688481.Majer and Svoboda, 1985 

Antoine Equation Parameters

log10(P) = A − (B / (T + C))
    P = vapor pressure (atm)
    T = temperature (K)

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Temperature (K) A B C Reference Comment
276.19 - 343.744.041561098.619-39.889Scott, Waddington, et al., 1949Coefficents calculated by NIST from author's data.

Enthalpy of fusion

DeltafusH (kcal/mol) Temperature (K) Reference Comment
1.811139.40Chao, Hall, et al., 1983DH
1.8158139.42Todd, Oliver, et al., 1947DH
1.81139.4Domalski and Hearing, 1996AC
1.777138.9Parks and Huffman, 1930DH

Entropy of fusion

DeltafusS (cal/mol*K) Temperature (K) Reference Comment
12.99139.40Chao, Hall, et al., 1983DH
13.02139.42Todd, Oliver, et al., 1947DH
1.28138.9Parks and Huffman, 1930DH

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

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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
Deltar-1.6 ± 0.72kcal/molEqkRihko, Linnekoski, et al., 1994liquid phase; solvent: Methanol/H+; ALS
Deltar-1.9 ± 0.33kcal/molEqkRihko, Linnekoski, et al., 1994liquid phase; solvent: Ethanol/H+; ALS

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

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

Quantity Value Units Method Reference Comment
Deltar38.2kcal/molPHPMSLi and Stone, 1989gas phase; condesation; M
Quantity Value Units Method Reference Comment
Deltar48.0cal/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
Deltar-7.84kcal/molEqkSerda, Izquierdo, et al., 1995liquid phase; ALS
Deltar-6.41 ± 0.55kcal/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
Deltar-14.12 ± 0.22kcal/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
Deltar-6.5 ± 1.6kcal/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
Deltar-9.11 ± 0.04kcal/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
Deltar3.40 ± 0.35kcal/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
Deltar1.93 ± 0.12kcal/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
Deltar-30.40 ± 0.20kcal/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
Deltar-26.68 ± 0.06kcal/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
Deltar-7.84 ± 0.33kcal/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
Deltar8.16 ± 0.19kcal/molEqkSharonov, Rozhnov, et al., 1995liquid phase; ALS

IR Spectrum

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change 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 compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director

Gas Phase Spectrum

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IR spectrum
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Additional Data

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Owner NIST Standard Reference Data Program
Collection (C) 2018 copyright by the U.S. Secretary of Commerce
on behalf of the United States of America. All rights reserved.
Origin Sadtler Research Labs Under US-EPA Contract
State gas

This IR spectrum is from the NIST/EPA Gas-Phase Infrared Database .


Mass spectrum (electron ionization)

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, IR Spectrum, 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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Mass spectrum
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Additional Data

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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

All mass spectra in this site (plus many more) are available from the NIST/EPA/NIH Mass Spectral Library. Please see the following for information about the library and its accompanying search program.


References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, IR Spectrum, 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]

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]

Parks and Huffman, 1930
Parks, G.S.; Huffman, H.M., Thermal data on organic compounds. IX. A study of the effect of unsaturation on the heat capacities, entropies and free energies of some hydrocarbons and other compounds, J. Am. Chem. Soc., 1930, 52, 4381-4391. [all data]

Chao, Hall, et al., 1983, 2
Chao, J.; Hall, K.R.; Yao, J.M., Thermodynamic Properties of Simple Alkenes, Thermochim. Acta, 1983, 64, 285. [all data]

Todd, Oliver, et al., 1947, 2
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. [all data]

Huffman, 1945
Huffman, H.M., Personal Commun., U. S. Bur. Mines, Bartlesville, OK, July 25, 1945. [all data]

Parks and Huffman, 1930, 2
Parks, G.S.; Huffman, H.M., Thermal data on organic compounds. IX. A study of the effect of unsaturation on the heat capacities, entropies and free energies of some hydrocarbons and other compounds, J. Am. Chem. Soc., 1930, 52, 4381. [all data]

Tsonopoulos and Ambrose, 1996
Tsonopoulos, C.; Ambrose, D., Vapor-Liquid Critical Properties of Elements and Compounds. 6. Unsaturated Aliphatic Hydrocarbons, J. Chem. Eng. Data, 1996, 41, 645-656. [all data]

Majer and Svoboda, 1985
Majer, V.; Svoboda, V., Enthalpies of Vaporization of Organic Compounds: A Critical Review and Data Compilation, Blackwell Scientific Publications, Oxford, 1985, 300. [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]

Scott, Waddington, et al., 1949
Scott, D.W.; Waddington, G.; Smith, J.C.; Huffman, H.M., Thermodynamic properties of three isomeric pentenes, J. Am. Chem. Soc., 1949, 71, 2767-2773. [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]

Domalski and Hearing, 1996
Domalski, Eugene S.; Hearing, Elizabeth D., Heat Capacities and Entropies of Organic Compounds in the Condensed Phase. Volume III, J. Phys. Chem. Ref. Data, 1996, 25, 1, 1, https://doi.org/10.1063/1.555985 . [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]


Notes

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, IR Spectrum, Mass spectrum (electron ionization), References