2-Pentene, 4,4-dimethyl-, (E)-
- Formula: C7H14
- Molecular weight: 98.1861
- IUPAC Standard InChIKey: BIDIHFPLDRSAMB-AATRIKPKSA-N
- CAS Registry Number: 690-08-4
- Chemical structure:
This structure is also available as a 2d Mol file or as a computed 3d SD file
The 3d structure may be viewed using Java or Javascript. - Stereoisomers:
- Other names: (E)-4,4-Dimethyl-2-pentene; trans-4,4-Dimethyl-2-Pentene; 4,4-Dimethyl-trans-2-pentene; (E)-(CH3)3CCH=CHCH3; 4,4-Dimethyl-2-pentene, trans; 4,4-Dimethyl-(E)-2-pentene; trans-1,1,1-Trimethyl-2-butene; (E)-4,4-dimethylpent-2-ene
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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 |
---|---|---|---|---|---|
ΔcH°liquid | -1107.46 ± 0.20 | kcal/mol | Ccb | Rockenfeller and Rossini, 1961 | Derived from the ratio of Heat of combustion; Corresponding ΔfHºliquid = -29.10 kcal/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 |
---|---|---|---|---|---|
Tboil | 349.7 ± 0.6 | K | AVG | N/A | Average of 8 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 157.84 | K | N/A | Boord, Greenlee, et al., 1950 | Uncertainty assigned by TRC = 0.2 K; TRC |
Tfus | 157.88 | K | N/A | Streiff, Soule, et al., 1950 | Uncertainty assigned by TRC = 0.06 K; TRC |
Tfus | 157.91 | K | N/A | Streiff, Soule, et al., 1950 | Uncertainty assigned by TRC = 0.02 K; TRC |
Tfus | 157.82 | K | N/A | Boord, Greenlee, et al., 1949 | Uncertainty assigned by TRC = 0.4 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 7.84 | kcal/mol | N/A | Reid, 1972 | AC |
ΔvapH° | 7.85 | kcal/mol | V | Camin and Rossini, 1960 | ALS |
Enthalpy of vaporization
ΔvapH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
7.84 | 310. | A | Stephenson and Malanowski, 1987 | Based on data from 295. to 352. K.; AC |
7.89 | 304. | MM | Camin and Rossini, 1960, 2 | Based on data from 289. to 350. K.; AC |
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
By formula: H2 + C7H14 = C7H16
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -27.29 ± 0.1 | kcal/mol | Chyd | Rogers and Dejroongruang, 1989 | liquid phase; solvent: Cyclohexane |
ΔrH° | -26.5 | kcal/mol | Chyd | Turner, Nettleton, et al., 1958 | liquid 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 ± 0.008 | PE | Masclet, Grosjean, et al., 1973 | LLK |
Mass spectrum (electron ionization)
Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Gas Chromatography, 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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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 |
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
Column type | Active phase | Temperature (C) | I | Reference | Comment |
---|---|---|---|---|---|
Capillary | Methyl Silicone | 30. | 625.5 | Soják, Addová, et al., 2002 | He; Column length: 150. m; Column diameter: 0.250 mm |
Capillary | Squalane | 30. | 614.8 | Soják, Addová, et al., 2002 | He; Column length: 93. m; Column diameter: 0.250 mm |
Capillary | OV-101 | 40. | 622. | Laub and Purnell, 1988 | |
Capillary | OV-101 | 60. | 621. | Laub and Purnell, 1988 | |
Capillary | OV-101 | 80. | 621. | Laub and Purnell, 1988 | |
Capillary | OV-101 | 50. | 621.3 | Boneva and Dimov, 1986 | 100. m/0.27 mm/0.9 μm, N2 |
Capillary | OV-101 | 70. | 621.2 | Boneva and Dimov, 1986 | 100. m/0.27 mm/0.9 μm, N2 |
Capillary | Squalane | 50. | 614.7 | Boneva and Dimov, 1986 | N2; Column length: 100. m; Column diameter: 0.25 mm |
Capillary | Squalane | 70. | 614.7 | Boneva and Dimov, 1986 | N2; Column length: 100. m; Column diameter: 0.25 mm |
Capillary | DB-1 | 40. | 625. | Lubeck and Sutton, 1984 | 60. m/0.264 mm/0.25 μm, H2 |
Capillary | HP-PONA | 40. | 625. | Lubeck and Sutton, 1984 | 50. m/0.21 mm/0.5 μm, H2 |
Packed | Squalane | 80. | 615. | Chrétien and Dubois, 1977 | |
Capillary | Squalane | 100. | 617. | Lulova, Leont'eva, et al., 1976 | He; Column length: 120. m; Column diameter: 0.25 mm |
Capillary | Squalane | 50. | 615. | Rijks and Cramers, 1974 | N2; Column length: 100. m; Column diameter: 0.25 mm |
Capillary | Squalane | 70. | 615. | Rijks and Cramers, 1974 | N2; Column length: 100. m; Column diameter: 0.25 mm |
Capillary | Squalane | 40. | 617. | Matukuma, 1969 | N2; Column length: 91.4 m; Column diameter: 0.25 mm |
Packed | Squalane | 27. | 615. | Hively and Hinton, 1968 | He, Chromosorb P; Column length: 15. m; Column diameter: 0.25 mm |
Packed | Squalane | 49. | 615. | Hively and Hinton, 1968 | He, Chromosorb P; Column length: 15. m; Column diameter: 0.25 mm |
Packed | Squalane | 67. | 615. | Hively and Hinton, 1968 | He, Chromosorb P; Column length: 15. m; Column diameter: 0.25 mm |
Packed | Squalane | 86. | 615. | Hively and Hinton, 1968 | He, Chromosorb P; Column length: 15. m; Column diameter: 0.25 mm |
Packed | Squalane | 30. | 614.5 | Tourres, 1967 | H2; Column length: 10. m |
Packed | Squalane | 50. | 615. | Tourres, 1967 | H2; Column length: 10. m |
Packed | Squalane | 26. | 617. | Zulaïca and Guiochon, 1966 | Column length: 10. m |
Kovats' RI, non-polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | Petrocol DH-100 | 623.1 | Haagen-Smit Laboratory, 1997 | He; 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
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | Methyl Silicone | 625.9 | Soják, Addová, et al., 2002 | He, 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
Column type | Active phase | Temperature (C) | I | Reference | Comment |
---|---|---|---|---|---|
Capillary | Squalane | 40. | 614.8 | Sojak, Addova, et al., 2000 | He; Column length: 93. m; Column diameter: 0.25 mm |
Capillary | Methyl Silicone | 40. | 614. | Meng and Liu, 1991 | 115. m/0.20 mm/0.30 μm |
Capillary | Methyl Silicone | 50. | 615. | N/A | N2; Column length: 74.6 m; Column diameter: 0.28 mm |
Capillary | Squalane | 60. | 616. | Lehmkuhl, Olbrysch, et al., 1975 | Nitrogen; Column length: 100. m |
Normal alkane RI, non-polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | Polydimethyl siloxane: CP-Sil 5 CB | 611. | Bramston-Cook, 2013 | 60. m/0.25 mm/1.0 μm, Helium, 45. C @ 1.45 min, 3.6 K/min, 210. C @ 2.72 min |
Capillary | Petrocol DH | 622. | Supelco, 2012 | 100. m/0.25 mm/0.50 μm, Helium, 20. C @ 15. min, 15. K/min, 220. C @ 30. min |
Capillary | PONA | 622. | Zhang, Ding, et al., 2009 | 50. m/0.20 mm/0.50 μm, Nitrogen, 35. C @ 15. min, 2. K/min, 200. C @ 10. min |
Capillary | OV-101 | 620. | Orav, Kailas, et al., 1999 | 50. m/0.20 mm/0.50 μm, Helium, 30. C @ 6. min, 1. K/min; Tend: 100. C |
Normal alkane RI, non-polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | Polydimethyl siloxane | 615. | Junkes, Castanho, et al., 2003 | Program: not specified |
Capillary | Methyl Silicone | 615. | Meng and Liu, 1991 | 115. m/0.20 mm/0.30 μm; Program: not specified |
References
Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Mass spectrum (electron ionization), Gas Chromatography, 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, Mass spectrum (electron ionization), Gas Chromatography, References
- Symbols used in this document:
Tboil Boiling point Tfus Fusion (melting) point ΔcH°liquid Enthalpy of combustion of liquid at standard conditions ΔrH° Enthalpy of reaction at standard conditions ΔvapH Enthalpy of vaporization ΔvapH° Enthalpy of vaporization at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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