1-Propene, 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
GT - Glushko Thermocenter, Russian Academy of Sciences, Moscow

Quantity Value Units Method Reference Comment
Δfgas-17.9 ± 1.1kJ/molCmProsen, Maron, et al., 1951ALS
Quantity Value Units Method Reference Comment
Δcgas-2699.5 ± 1.0kJ/molCmProsen, Maron, et al., 1951Corresponding Δfgas = -17.9 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS
Δcgas-2722.kJ/molCcbGuinchant, 1918Corresponding Δfgas = 4.6 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS
Quantity Value Units Method Reference Comment
gas293.59J/mol*KN/AStull D.R., 1969This value was obtained on the basis of calorimetric data [ Todd S.S., 1936]. Experimental value of S(298 K)=288.7 J/mol*K [ Todd S.S., 1936] could not be recommended because of its large uncertainty.; GT

Constant pressure heat capacity of gas

Cp,gas (J/mol*K) Temperature (K) Reference Comment
35.6850.Thermodynamics Research Center, 1997p=1 bar. Recommended values are in close agreement with other statistically calculated values [ Kilpatrick J.E., 1946] as well as with ab initio value of S(298.15 K)=293.37 J/mol*K [ East A.L.L., 1997].; GT
45.92100.
56.83150.
67.34200.
82.72273.15
88.09298.15
88.49300.
109.79400.
129.35500.
146.48600.
161.35700.
174.30800.
185.59900.
195.451000.
204.031100.
211.501200.
217.991300.
223.651400.
228.581500.
238.391750.
245.512000.
250.792250.
254.782500.
257.832750.
260.203000.

Constant pressure heat capacity of gas

Cp,gas (J/mol*K) Temperature (K) Reference Comment
75.86 ± 0.38239.15Scott R.B., 1945GT
82.89 ± 0.41272.15
91.67 ± 0.46312.15
100.25 ± 0.50353.15

Phase change data

Go To: Top, Gas 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 as indicated in comments:
DH - Eugene S. Domalski and Elizabeth D. Hearing
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

Quantity Value Units Method Reference Comment
Tboil266.7 ± 0.7KAVGN/AAverage of 25 out of 28 values; Individual data points
Quantity Value Units Method Reference Comment
Tfus132.38KN/ARabinovich and Lebedev, 1971DH
Tfus132.45KN/AKistiakowsky, Ruhoff, et al., 1935Uncertainty assigned by TRC = 0.3 K; TRC
Tfus125.4KN/ACoffin and Maass, 1928Uncertainty assigned by TRC = 0.5 K; TRC
Quantity Value Units Method Reference Comment
Ttriple132.4KN/ATodd and Parks, 1936Uncertainty assigned by TRC = 0.2 K; TRC
Quantity Value Units Method Reference Comment
Tc417.9 ± 0.1KN/ATsonopoulos and Ambrose, 1996 
Tc417.88KN/ABeattie, Ingersoll, et al., 1942Uncertainty assigned by TRC = 0.1 K; TRC
Tc420.15KN/ACoffin and Maass, 1928Uncertainty assigned by TRC = 2. K; TRC
Quantity Value Units Method Reference Comment
Pc40.00 ± 0.10barN/ATsonopoulos and Ambrose, 1996 
Pc40.0031barN/ABeattie, Ingersoll, et al., 1942Uncertainty assigned by TRC = 0.1013 bar; TRC
Quantity Value Units Method Reference Comment
Vc0.2388l/molN/ATsonopoulos and Ambrose, 1996 
Quantity Value Units Method Reference Comment
ρc4.19 ± 0.010mol/lN/ATsonopoulos and Ambrose, 1996 
ρc4.17mol/lN/ABeattie, Ingersoll, et al., 1942Uncertainty assigned by TRC = 0.05 mol/l; TRC
Quantity Value Units Method Reference Comment
Δvap20.6kJ/molN/AReid, 1972AC

Enthalpy of vaporization

ΔvapH (kJ/mol) Temperature (K) Method Reference Comment
23.1264.AStephenson and Malanowski, 1987Based on data from 212. to 279. K.; AC
22.7281.AStephenson and Malanowski, 1987Based on data from 266. to 313. K.; AC
22.2325.AStephenson and Malanowski, 1987Based on data from 310. to 376. K.; AC
22.3386.AStephenson and Malanowski, 1987Based on data from 371. to 418. K.; AC
22.2350.N/ABeattie, Ingersoll, et al., 1942, 2Based on data from 303. to 398. K.; AC
22.8258.N/ALamb and Roper, 1940Based on data from 216. to 273. K. See also Boublik, Fried, et al., 1984.; AC

Antoine Equation Parameters

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

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Temperature (K) A B C Reference Comment
216.40 to 273.3.64709799.055-46.615Lamb and Roper, 1940Coefficents calculated by NIST from author's data.

Enthalpy of fusion

ΔfusH (kJ/mol) Temperature (K) Reference Comment
5.92132.4Domalski and Hearing, 1996AC
5.920132.4Todd and Parks, 1936, 2DH

Entropy of fusion

ΔfusS (J/mol*K) Temperature (K) Reference Comment
44.71132.4Todd and Parks, 1936, 2DH

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:


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:
HL - Edward P. Hunter and Sharon G. Lias
L - Sharon G. Lias

Data compiled as indicated in comments:
B - John E. Bartmess
MM - Michael M. Meot-Ner (Mautner)
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 C4H8+ (ion structure unspecified)

Quantity Value Units Method Reference Comment
IE (evaluated)9.22 ± 0.02eVN/AN/AL
Quantity Value Units Method Reference Comment
Proton affinity (review)802.1kJ/molN/AHunter and Lias, 1998HL
Quantity Value Units Method Reference Comment
Gas basicity775.6kJ/molN/AHunter and Lias, 1998HL

Proton affinity at 298K

Proton affinity (kJ/mol) Reference Comment
802.3 ± 4.8Bouchoux and Salpin, 1999T = 300K; Re-evaluated thermokinetic parametric fitting by the authors using reference base GBs and PAs from Hunter and Lias, 1998; MM
802.3 ± 4.8Bouchoux and Salpin, 1999T = 298K; MM
805.0 ± 6.7Cleven, Hoke, et al., 1996PA > butyronitrile, < benzonitrile; MM

Gas basicity at 298K

Gas basicity (review) (kJ/mol) Reference Comment
776.3 ± 2.7Bouchoux and Salpin, 1999T = 300K; Re-evaluated thermokinetic parametric fitting by the authors using reference base GBs and PAs from Hunter and Lias, 1998; MM
776.3 ± 2.7Bouchoux and Salpin, 1999T = 298K; MM

Ionization energy determinations

IE (eV) Method Reference Comment
9.19PITraeger, 1986LBLHLM
9.24 ± 0.05EIHolmes and Lossing, 1983LBLHLM
9.24 ± 0.02PEBieri, Burger, et al., 1977LLK
9.239 ± 0.003PEMasclet, Grosjean, et al., 1973LLK
9.19EILossing, 1972LLK
9.21PEFrost and Sandhu, 1971LLK
9.17PEDewar and Worley, 1969RDSH
9.23 ± 0.02PIWatanabe, Nakayama, et al., 1962RDSH
9.23PIBralsford, Harris, et al., 1960RDSH
9.41PEWiberg, Ellison, et al., 1976Vertical value; LLK
9.39PEKoenig, Balle, et al., 1975Vertical value; LLK
9.45PEKimura, Katsumata, et al., 1975Vertical value; LLK

Appearance energy determinations

Ion AE (eV) Other Products MethodReferenceComment
CH3+16.4C3H5EISenSharma and Franklin, 1973LLK
C2H4+12.0 ± 0.25?EIMeisels, Park, et al., 1970RDSH
C3H5+11.33CH3PITraeger, 1984LBLHLM
C3H5+11.8CH3EISenSharma and Franklin, 1973LLK
C3H5+11.45CH3EILossing, 1972LLK
C4H6+11.3 ± 0.1H2EIHolmes, Weese, et al., 1977LLK
C4H7+11.26HPITraeger, 1986LBLHLM
C4H7+11.41HEILossing, 1972LLK

De-protonation reactions

C4H7- + Hydrogen cation = 1-Propene, 2-methyl-

By formula: C4H7- + H+ = C4H8

Quantity Value Units Method Reference Comment
Δr1644. ± 7.5kJ/molEndoWenthold, Hu, et al., 1999gas phase; B
Δr1619. ± 8.4kJ/molD-EAWenthold, Polak, et al., 1996gas phase; B
Δr1633. ± 9.6kJ/molG+TSBartmess and Burnham, 1984gas phase; B
Quantity Value Units Method Reference Comment
Δr1613. ± 7.9kJ/molH-TSWenthold, Hu, et al., 1999gas phase; B
Δr1588. ± 8.8kJ/molH-TSWenthold, Polak, et al., 1996gas phase; B
Δr1602. ± 9.2kJ/molIMREBartmess and Burnham, 1984gas phase; B

References

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

Prosen, Maron, et al., 1951
Prosen, E.J.; Maron, F.W.; Rossini, F.D., Heats of combustion, formation, and insomerization of ten C4 hydrocarbons, J. Res. NBS, 1951, 46, 106-112. [all data]

Guinchant, 1918
Guinchant, M.J., Etude sur la fonction acide dans les derives metheniques et methiniques, Ann. Chem., 1918, 10, 30-84. [all data]

Stull D.R., 1969
Stull D.R., Jr., The Chemical Thermodynamics of Organic Compounds. Wiley, New York, 1969. [all data]

Todd S.S., 1936
Todd S.S., Thermal data on organic compounds. XV. Some heat capacity, entropy and free energy data for the isomeric butenes, J. Am. Chem. Soc., 1936, 58, 134-137. [all data]

Thermodynamics Research Center, 1997
Thermodynamics Research Center, Selected Values of Properties of Chemical Compounds., Thermodynamics Research Center, Texas A&M University, College Station, Texas, 1997. [all data]

Kilpatrick J.E., 1946
Kilpatrick J.E., Heat content, free energy function, entropy, and heat capacity of ethylene, propylene, and the four butenes to 1500 K, J. Res. Nat. Bur. Stand, 1946, 37, 163-171. [all data]

East A.L.L., 1997
East A.L.L., Ab initio statistical thermodynamical models for the computation of third-law entropies, J. Chem. Phys., 1997, 106, 6655-6674. [all data]

Scott R.B., 1945
Scott R.B., Specific heats of gaseous 1,3-butadiene, isobutene, styrene, and ethylbenzene, J. Res. Nat. Bur. Stand., 1945, 34, 243-254. [all data]

Rabinovich and Lebedev, 1971
Rabinovich, I.B.; Lebedev, B.V., On the thermodynamic stability of polyisobutylene. Tr. Khim. Khim. Tekhnol., 1971, 194-196. [all data]

Kistiakowsky, Ruhoff, et al., 1935
Kistiakowsky, G.B.; Ruhoff, J.R.; Smith, H.A.; Vaughan, W.E., Heats of Organic Reactions II. Hydrogenation of Some Simpler Olefinic Hydrocarbons, J. Am. Chem. Soc., 1935, 57, 876-82. [all data]

Coffin and Maass, 1928
Coffin, C.C.; Maass, O., The Preparation and Physical Properties of α-,β- and γ-Butylene and Normal and Isobutane, J. Am. Chem. Soc., 1928, 50, 1427-37. [all data]

Todd and Parks, 1936
Todd, S.S.; Parks, G.S., Thermal Data on Organic Compounds XV. Some Heat Capacity, Entropy and Free Energy Data for the Isomeric Butenes, J. Am. Chem. Soc., 1936, 58, 134. [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]

Beattie, Ingersoll, et al., 1942
Beattie, J.A.; Ingersoll, H.G.; Stockmayer, W.H., Vapor Pressure and Critical Consants of Isobutene, J. Am. Chem. Soc., 1942, 64, 546. [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]

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]

Beattie, Ingersoll, et al., 1942, 2
Beattie, James A.; Ingersoll, Henry G.; Stockmayer, Walter H., Vapor Pressures and Critical Constants of Isobutene, J. Am. Chem. Soc., 1942, 64, 3, 546-548, https://doi.org/10.1021/ja01255a021 . [all data]

Lamb and Roper, 1940
Lamb, Arthur B.; Roper, Edwin E., The Vapor Pressures of Certain Unsaturated Hydrocarbons, J. Am. Chem. Soc., 1940, 62, 4, 806-814, https://doi.org/10.1021/ja01861a032 . [all data]

Boublik, Fried, et al., 1984
Boublik, T.; Fried, V.; Hala, E., The Vapour Pressures of Pure Substances: Selected Values of the Temperature Dependence of the Vapour Pressures of Some Pure Substances in the Normal and Low Pressure Region, 2nd ed., Elsevier, New York, 1984, 972. [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]

Todd and Parks, 1936, 2
Todd, S.S.; Parks, G.S., Thermal data on organic compounds. XV. Some heat capacity, entropy and free energy data for the isomeric butenes, J. Am. Chem. Soc., 1936, 58, 134-137. [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]

Bouchoux and Salpin, 1999
Bouchoux, J.; Salpin, J.Y., Re-evaluated gas-phase basicity and proton affinity data from the thermokinetic method, Rapid Com. Mass Spectrom., 1999, 13, 932. [all data]

Cleven, Hoke, et al., 1996
Cleven, C.D.; Hoke, S.H.; Cooks, R.G.; Hrovat, D.A.; Smith, J.M.; Lee, M.S.; Borden, W.T., Effect of Olefin Pyramidalization on the Proton Affinity of Tricyclo[3.3.3.03,7]undec-3(7)-ene as Determined by ab Initio Calculations and Kinetic Method Measurements, J. Am. Chem. Soc., 1996, 118, 10872. [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]

Holmes and Lossing, 1983
Holmes, J.L.; Lossing, F.P., The need for adequate thermochemical data for the interpretation of fragmentation mechanisms and ion structure assignments, Int. J. Mass Spectrom. Ion Phys., 1983, 47, 133. [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]

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]

Dewar and Worley, 1969
Dewar, M.J.S.; Worley, S.D., Photoelectron spectra of molecules. I. Ionization potentials of some organic molecules and their interpretation, J. Chem. Phys., 1969, 50, 654. [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]

Wiberg, Ellison, et al., 1976
Wiberg, K.B.; Ellison, G.B.; Wendoloski, J.J.; Brundle, C.R.; Kuebler, N.A., Electronic states of organic molecules. 3. Photoelectron spectra of cycloalkenes and methylenecycloalkanes, J. Am. Chem. Soc., 1976, 98, 7179. [all data]

Koenig, Balle, et al., 1975
Koenig, T.; Balle, T.; Snell, W., Helium(I) photoelectron spectra of organic radicals, J. Am. Chem. Soc., 1975, 97, 662. [all data]

Kimura, Katsumata, et al., 1975
Kimura, K.; Katsumata, S.; Yamazaki, T.; Wakabayashi, H., UV photoelectron spectra and sum rule consideration; out-of-plane orbitals of unsaturated compounds with planar-skeleton structure, J. Electron Spectrosc. Relat. Phenom., 1975, 6, 41. [all data]

SenSharma and Franklin, 1973
SenSharma, D.K.; Franklin, J.L., Heat of formation of free radicals by mass spectrometry, J. Am. Chem. Soc., 1973, 95, 6562. [all data]

Meisels, Park, et al., 1970
Meisels, G.G.; Park, J.Y.; Giessner, B.G., Ionization and dissociation of C4H8 isomers, J. Am. Chem. Soc., 1970, 92, 254. [all data]

Traeger, 1984
Traeger, J.C., A study of the allyl cation thermochemistry by photoionization mass spectrometry, Int. J. Mass Spectrom. Ion Processes, 1984, 58, 259. [all data]

Holmes, Weese, et al., 1977
Holmes, J.L.; Weese, G.M.; Blair, A.S.; Terlouw, J.K., Metastable ion studies IX-Thermochemistry and ion structures among fragmenting [C4H8]+ ions, an electron impact and field ionization investigation, Org. Mass Spectrom., 1977, 12, 424. [all data]

Wenthold, Hu, et al., 1999
Wenthold, P.G.; Hu, J.; Squires, R.R.; Lineberger, W.C., Photoelectron spectroscopy of the trimethylenemethane negative ion, J. Am. Soc. Mass Spectrom., 1999, 10, 9, 800-809, https://doi.org/10.1016/S1044-0305(99)00043-4 . [all data]

Wenthold, Polak, et al., 1996
Wenthold, P.G.; Polak, M.L.; Lineberger, W.C., Photoelectron Spectroscopy of the Allyl and 2-Methylallyl Anions, J. Phys. Chem., 1996, 100, 17, 6920, https://doi.org/10.1021/jp953401n . [all data]

Bartmess and Burnham, 1984
Bartmess, J.E.; Burnham, R., Effect of central substituents on the gas phase acidities of propenes, J. Org. Chem., 1984, 49, 1382. [all data]


Notes

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