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2-Pentene, 4,4-dimethyl-, (E)-

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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 by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Quantity Value Units Method Reference Comment
Deltacliquid-4633.61 ± 0.84kJ/molCcbRockenfeller and Rossini, 1961Derived from the ratio of Heat of combustion; Corresponding «DELTA»fliquid = -121.8 kJ/mol (simple calculation by NIST; no Washburn corrections)

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
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Quantity Value Units Method Reference Comment
Tboil349.7 ± 0.6KAVGN/AAverage of 8 values; Individual data points
Quantity Value Units Method Reference Comment
Tfus157.84KN/ABoord, Greenlee, et al., 1950Uncertainty assigned by TRC = 0.2 K; TRC
Tfus157.88KN/AStreiff, Soule, et al., 1950Uncertainty assigned by TRC = 0.06 K; TRC
Tfus157.91KN/AStreiff, Soule, et al., 1950Uncertainty assigned by TRC = 0.02 K; TRC
Tfus157.82KN/ABoord, Greenlee, et al., 1949Uncertainty assigned by TRC = 0.4 K; TRC
Quantity Value Units Method Reference Comment
Deltavap32.8kJ/molN/AReid, 1972AC
Deltavap32.8kJ/molVCamin and Rossini, 1960ALS

Enthalpy of vaporization

DeltavapH (kJ/mol) Temperature (K) Method Reference Comment
32.8310.AStephenson and Malanowski, 1987Based on data from 295. - 352. K.; AC
33.0304.MMCamin and Rossini, 1960, 2Based on data from 289. - 350. K.; AC

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 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-Pentene, 4,4-dimethyl-, (E)- = Pentane, 2,2-dimethyl-

By formula: H2 + C7H14 = C7H16

Quantity Value Units Method Reference Comment
Deltar-114.2 ± 0.4kJ/molChydRogers and Dejroongruang, 1989liquid phase; solvent: Cyclohexane
Deltar-111.kJ/molChydTurner, Nettleton, et al., 1958liquid phase; solvent: Acetic acid

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 compiled as indicated in comments:
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi

Ionization energy determinations

IE (eV) Method Reference Comment
8.908 ± 0.008PEMasclet, Grosjean, et al., 1973LLK

IR Spectrum

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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: 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)

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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: 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.
NIST MS number 908

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.


Gas Chromatography

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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: NIST Mass Spectrometry Data Center, William E. Wallace, director

Kovats' RI, non-polar column, isothermal

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Column type Active phase Temperature (C) I Reference Comment
CapillaryMethyl Silicone30.625.5Soják, Addová, et al., 2002He; Column length: 150. m; Column diameter: 0.250 mm
CapillarySqualane30.614.8Soják, Addová, et al., 2002He; Column length: 93. m; Column diameter: 0.250 mm
CapillaryOV-10140.622.Laub and Purnell, 1988 
CapillaryOV-10160.621.Laub and Purnell, 1988 
CapillaryOV-10180.621.Laub and Purnell, 1988 
CapillaryOV-10150.621.3Boneva and Dimov, 1986100. m/0.27 mm/0.9 «mu»m, N2
CapillaryOV-10170.621.2Boneva and Dimov, 1986100. m/0.27 mm/0.9 «mu»m, N2
CapillarySqualane50.614.7Boneva and Dimov, 1986N2; Column length: 100. m; Column diameter: 0.25 mm
CapillarySqualane70.614.7Boneva and Dimov, 1986N2; Column length: 100. m; Column diameter: 0.25 mm
CapillaryDB-140.625.Lubeck and Sutton, 198460. m/0.264 mm/0.25 «mu»m, H2
CapillaryHP-PONA40.625.Lubeck and Sutton, 198450. m/0.21 mm/0.5 «mu»m, H2
PackedSqualane80.615.Chrétien and Dubois, 1977 
CapillarySqualane100.617.Lulova, Leont'eva, et al., 1976He; Column length: 120. m; Column diameter: 0.25 mm
CapillarySqualane50.615.Rijks and Cramers, 1974N2; Column length: 100. m; Column diameter: 0.25 mm
CapillarySqualane70.615.Rijks and Cramers, 1974N2; Column length: 100. m; Column diameter: 0.25 mm
CapillarySqualane40.617.Matukuma, 1969N2; Column length: 91.4 m; Column diameter: 0.25 mm
PackedSqualane27.615.Hively and Hinton, 1968He, Chromosorb P; Column length: 15. m; Column diameter: 0.25 mm
PackedSqualane49.615.Hively and Hinton, 1968He, Chromosorb P; Column length: 15. m; Column diameter: 0.25 mm
PackedSqualane67.615.Hively and Hinton, 1968He, Chromosorb P; Column length: 15. m; Column diameter: 0.25 mm
PackedSqualane86.615.Hively and Hinton, 1968He, Chromosorb P; Column length: 15. m; Column diameter: 0.25 mm
PackedSqualane30.614.5Tourres, 1967H2; Column length: 10. m
PackedSqualane50.615.Tourres, 1967H2; Column length: 10. m
PackedSqualane26.617.Zulaïca and Guiochon, 1966Column length: 10. m

Kovats' RI, non-polar column, custom temperature program

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Column type Active phase I Reference Comment
CapillaryPetrocol DH-100623.1Haagen-Smit Laboratory, 1997He; Column length: 100. m; Column diameter: 0.2 mm; Program: 5C(10min) => 5C/min => 50C(48min) => 1.5C/min => 195C(91min)

Van Den Dool and Kratz RI, non-polar column, temperature ramp

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Column type Active phase I Reference Comment
CapillaryMethyl Silicone625.9Soják, Addová, et al., 2002He, 1. K/min; Column length: 150. m; Column diameter: 0.250 mm; Tstart: 30. C; Tend: 200. C

Normal alkane RI, non-polar column, isothermal

View large format table.

Column type Active phase Temperature (C) I Reference Comment
CapillarySqualane40.614.8Sojak, Addova, et al., 2000He; Column length: 93. m; Column diameter: 0.25 mm
CapillaryMethyl Silicone40.614.Meng and Liu, 1991115. m/0.20 mm/0.30 «mu»m
CapillaryMethyl Silicone50.615.N/AN2; Column length: 74.6 m; Column diameter: 0.28 mm
CapillarySqualane60.616.Lehmkuhl, Olbrysch, et al., 1975Nitrogen; Column length: 100. m

Normal alkane RI, non-polar column, temperature ramp

View large format table.

Column type Active phase I Reference Comment
CapillaryPolydimethyl siloxane: CP-Sil 5 CB611.Bramston-Cook, 201360. m/0.25 mm/1.0 «mu»m, Helium, 45. C @ 1.45 min, 3.6 K/min, 210. C @ 2.72 min
CapillaryPetrocol DH622.Supelco, 2012100. m/0.25 mm/0.50 «mu»m, Helium, 20. C @ 15. min, 15. K/min, 220. C @ 30. min
CapillaryPONA622.Zhang, Ding, et al., 200950. m/0.20 mm/0.50 «mu»m, Nitrogen, 35. C @ 15. min, 2. K/min, 200. C @ 10. min
CapillaryOV-101620.Orav, Kailas, et al., 199950. m/0.20 mm/0.50 «mu»m, Helium, 30. C @ 6. min, 1. K/min; Tend: 100. C

Normal alkane RI, non-polar column, custom temperature program

View large format table.

Column type Active phase I Reference Comment
CapillaryPolydimethyl siloxane615.Junkes, Castanho, et al., 2003Program: not specified
CapillaryMethyl Silicone615.Meng and Liu, 1991115. m/0.20 mm/0.30 «mu»m; Program: not specified

References

Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), Gas Chromatography, NIST Free Links, Notes

Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Rockenfeller and Rossini, 1961
Rockenfeller, J.D.; Rossini, F.D., Heats of combustion, isomerization, and formation of selected C7, C8, and C10 monoolefin hydrocarbons, J. Phys. Chem., 1961, 65, 267-272. [all data]

Boord, Greenlee, et al., 1950
Boord, C.E.; Greenlee, K.W.; Derfer, J.M., The Synthesis, Purification and Prop. of Hydrocarbons of Low Mol. Wt., Am. Pet. Inst. Res. Proj. 45, Twelfth Annu. Rep., Ohio State Univ., 1950. [all data]

Streiff, Soule, et al., 1950
Streiff, A.J.; Soule, L.F.; Kennedy, C.M.; Janes, M.E.; Sedlak, V.A.; Willingham, C.B.; Rossini, F.D., Purification, purity, and freezing points of twenty-nine hydrocarbons of the API-standard and API-NBS series., J. Res. Natl. Bur. Stand. (U. S.), 1950, 45, 173. [all data]

Boord, Greenlee, et al., 1949
Boord, C.E.; Greenlee, K.W.; Perilstein, W.L.; Derfer, J.M., The Synthesis, Purification and Prop. of Hydrocarbons of Low Mol. Wt., Am. Pet. Inst. Res. Proj. 45, Eleventh Annu. Rep., Ohio State Univ., 1949. [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]

Camin and Rossini, 1960
Camin, D.L.; Rossini, F.D., Physical properties of to selected C7 and C8 alkene hydrocarbons, J. Chem. Eng. Data, 1960, 5, 368. [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]

Camin and Rossini, 1960, 2
Camin, D.L.; Rossini, F.D., Physical Properties of 16 Selected C 7 and C 8 Alkene Hydrocarbons., J. Chem. Eng. Data, 1960, 5, 3, 368-372, https://doi.org/10.1021/je60007a037 . [all data]

Rogers and Dejroongruang, 1989
Rogers, D.W.; Dejroongruang, K., Enthalpies of hydrogenation of the dimethylpentenes, ethylpentenes, methylbutene, and trimethylbutene, J. Chem. Thermodyn., 1989, 21, 1115-1120. [all data]

Turner, Nettleton, et al., 1958
Turner, R.B.; Nettleton, J.E.; Perelman, Heats of Hydrogenation. VI. Heats of hydrogenation of some substituted ethylenes, J. Am. Chem. Soc., 1958, 80, 1430-1433. [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]

Soják, Addová, et al., 2002
Soják, L.; Addová, G.; Kubinec, R.; Kraus, A.; Hu, G., Gas chromatographic-mass spectrometric characterization of all acyclic C5-C7 alkenes from fluid catalytic cracked gasoline using polydimethylsiloxane and squalane stationary phases, J. Chromatogr. A, 2002, 947, 1, 103-117, https://doi.org/10.1016/S0021-9673(01)01564-3 . [all data]

Laub and Purnell, 1988
Laub, R.J.; Purnell, J.H., Specific retention volumes, retention indices, and family-plot regressions of aliphatic, alicyclic, and aromatic hydrocarbon solutes with OV-101 poly (dimethylsiloxane) stationary phase, J. Hi. Res. Chromatogr. Chromatogr. Comm., 1988, 11, 9, 649-660, https://doi.org/10.1002/jhrc.1240110908 . [all data]

Boneva and Dimov, 1986
Boneva, S.; Dimov, N., Gas Chromatographic Retention Indices for Alkenes on OV-101 and Squalane Capillary Columns, Chromatographia, 1986, 21, 3, 149-151, https://doi.org/10.1007/BF02311743 . [all data]

Lubeck and Sutton, 1984
Lubeck, A.J.; Sutton, D.L., Kovats Retention Indices of Selected Olefins on Bonded Phase Fused Silica Capillaries, J. Hi. Res. Chromatogr. Chromatogr. Comm., 1984, 7, 9, 542-544, https://doi.org/10.1002/jhrc.1240070913 . [all data]

Chrétien and Dubois, 1977
Chrétien, J.R.; Dubois, J.E., Topological analysis of gas-liquid chromatographic behavior of alkenes, Anal. Chem., 1977, 49, 6, 747-756, https://doi.org/10.1021/ac50014a021 . [all data]

Lulova, Leont'eva, et al., 1976
Lulova, N.I.; Leont'eva, S.A.; Timofeeva, A.N., Gas-chromatographic method of determination of individual hydrocarbons in catalytic cracking gasolines in Proceedings of All-Union Research Institute on Oil Processes. Vol.18, All-Union Research Institute on Oil Processes, Moscow, 1976, 30-53. [all data]

Rijks and Cramers, 1974
Rijks, J.A.; Cramers, C.A., High precision capillary gas chromatography of hydrocarbons, Chromatographia, 1974, 7, 3, 99-106, https://doi.org/10.1007/BF02269819 . [all data]

Matukuma, 1969
Matukuma, A., Retention indices of alkanes through C10 and alkenes through C8 and relation between boiling points and retention data, Gas Chromatogr., Int. Symp. Anal. Instrum. Div Instrum Soc. Amer., 1969, 7, 55-75. [all data]

Hively and Hinton, 1968
Hively, R.A.; Hinton, R.E., Variation of the retention index with temperature on squalane substrates, J. Gas Chromatogr., 1968, 6, 4, 203-217, https://doi.org/10.1093/chromsci/6.4.203 . [all data]

Tourres, 1967
Tourres, D.A., Structural analysis of industrial butene dimers by gas chromatography, J. Gas Chromatogr., 1967, 5, 1, 35-40, https://doi.org/10.1093/chromsci/5.1.35 . [all data]

Zulaïca and Guiochon, 1966
Zulaïca, J.; Guiochon, G., Analyse des hauts polymères par chromatographie en phase gazeuse de leurs produits de pyrolyse. II. Application à quelques hydrocarbures macromoléculaires purs, Bull. Soc. Chim. Fr., 1966, 4, 1351-1363. [all data]

Haagen-Smit Laboratory, 1997
Haagen-Smit Laboratory, Procedure for the detailed hydrocarbon analysis of gasolines by single column high efficiency (capillary) column gas chromatography, SOP NO. MLD 118, Revision No. 1.1, California Environmental Protection Agency, Air Resources Board, El Monte, California, 1997, 22. [all data]

Sojak, Addova, et al., 2000
Sojak, L.; Addova, G.; Kubinec, R.; Ruman, J.; Hu, G., GC-MS characterization of all acyclic C5-C7 alkenes from FCC gasoline using squalane stationary phase, Petroleum and Coal, 2000, 42, 3-4, 188-194. [all data]

Meng and Liu, 1991
Meng, W.; Liu, C., Gas chromatographic analysis of alkene imourities in solvent naphtha, China Synth. Rubber Ind., 1991, 14, 2, 109-111. [all data]

Lehmkuhl, Olbrysch, et al., 1975
Lehmkuhl, H.; Olbrysch, O.; Reinehr, D.; Schomburg, G.; Henneberg, D., Vergleich der Additionsrichtungen von tert.-Butyl und Isopropylverbindungen des Magnesiums, Aluminiums and Lithiums an 1-Alkene, Liebigs Ann. Chem., 1975, 1975, 1, 145-159, https://doi.org/10.1002/jlac.197519750114 . [all data]

Bramston-Cook, 2013
Bramston-Cook, R., Kovats indices for C2-C13 hydrocarbons and selected oxygenated/halocarbons with 100 % dimethylpolysiloxane columns, 2013, retrieved from http://lotusinstruments.com/monographs/List .... [all data]

Supelco, 2012
Supelco, CatalogNo. 24160-U, Petrocol DH Columns. Catalog No. 24160-U, 2012, retrieved from http://www.sigmaaldrich.com/etc/medialib/docs/Supelco/Datasheet/1/w97949.Par.0001.File.tmp/w97949.pdf. [all data]

Zhang, Ding, et al., 2009
Zhang, X.; Ding, L.; Sun, Z.; Song, L.; Sun, T., Study on quantitative structure-retention relationships for hydrocarbons in FCC gasoline, Chromatographia, 2009, 70, 3/4, 511-518, https://doi.org/10.1365/s10337-009-1174-0 . [all data]

Orav, Kailas, et al., 1999
Orav, A.; Kailas, T.; Muurisepp, M.; Kann, J., Composition of the oil from waste tires. 1. Fraction boiling at yp to 160 0C, Proc. Estonian Acad. Sci. Chem., 1999, 48, 1, 30-39. [all data]

Junkes, Castanho, et al., 2003
Junkes, B.S.; Castanho, R.D.M.; Amboni, C.; Yunes, R.A.; Heinzen, V.E.F., Semiempirical Topological Index: A Novel Molecular Descriptor for Quantitative Structure-Retention Relationship Studies, Internet Electronic Journal of Molecular Design, 2003, 2, 1, 33-49. [all data]


Notes

Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), Gas Chromatography, NIST Free Links, References