Cyclopentane, 1-ethyl-2-methyl-, cis-

Formula: C₈H₁₆
Molecular weight: 112.2126
IUPAC Standard InChI: InChI=1S/C8H16/c1-3-8-6-4-5-7(8)2/h7-8H,3-6H2,1-2H3/t7-,8+/m0/s1
IUPAC Standard InChIKey: BSKOLJVTLRLTHE-JGVFFNPUSA-N
CAS Registry Number: 930-89-2
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: cis-1-Ethyl-2-Methylcyclopentane; cis-1-Methyl-2-ethylcyclopentane; 1-Methyl-cis-2-ethylcyclopentane; c-1-Ethyl-2-methylcyclopentane; 1-Ethyl-2-methylcyclopentane, (Z)-; 1-Ethyl-2-methylcyclopentane, cis
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- Mass spectrum (electron ionization)
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Condensed phase thermochemistry data

Go To: Top, Phase change data, Gas Chromatography, References, Notes

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

Quantity	Value	Units	Method	Reference	Comment
Δ_fH°_liquid	-190.8 ± 1.0	kJ/mol	Ccr	Good, 1971
Quantity	Value	Units	Method	Reference	Comment
Δ_cH°_liquid	-5243.89 ± 0.92	kJ/mol	Ccr	Good, 1971	Corresponding Δ_fHº_liquid = -190.8 kJ/mol (simple calculation by NIST; no Washburn corrections)

Phase change data

Go To: Top, Condensed phase thermochemistry data, Gas Chromatography, References, Notes

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

Quantity	Value	Units	Method	Reference	Comment
T_boil	401.1 ± 0.1	K	AVG	N/A	Average of 6 values; Individual data points
Quantity	Value	Units	Method	Reference	Comment
T_fus	190. ± 100.	K	AVG	N/A	Average of 8 values; Individual data points
Quantity	Value	Units	Method	Reference	Comment
Δ_vapH°	40.2	kJ/mol	N/A	Reid, 1972	AC

Enthalpy of vaporization

Δ_vapH (kJ/mol)	Temperature (K)	Method	Reference	Comment
42.5	253.	A	Stephenson and Malanowski, 1987	Based on data from 238. to 304. K.; AC
39.3	318.	A	Stephenson and Malanowski, 1987	Based on data from 303. to 403. K.; AC
41.6	273.	IP	Osborn and Douslin, 1974	Based on data from 238. to 288. K.; AC
38.3	337.	N/A	Forziati, Norris, et al., 1949	Based on data from 322. to 402. K.; 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
238. to 288.	4.7961	1760.951	-27.21	Osborn and Douslin, 1974	Coefficents calculated by NIST from author's data.
322.00 to 402.17	4.04224	1395.706	-55.428	Forziati, Norris, et al., 1949, 2	Coefficents calculated by NIST from author's data.

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 Chromatography

Go To: Top, Condensed phase thermochemistry data, Phase change data, References, Notes

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

Kovats' RI, non-polar column, isothermal

View large format table.

Column type	Active phase	Temperature (C)	I	Reference	Comment
Capillary	Squalane	50.	820.1	Lunskii and Paizanskaya, 1988	He; Column length: 50. m; Column diameter: 0.22 mm
Capillary	Squalane	70.	825.3	Lunskii and Paizanskaya, 1988	He; Column length: 50. m; Column diameter: 0.22 mm
Capillary	Squalane	50.	820.7	Krupcik, Cellar, et al., 1986	Column length: 180. m; Column diameter: 0.25 mm
Capillary	DB-1	60.	820.3	Lubeck and Sutton, 1983	Column length: 60. m; Column diameter: 0.264 mm
Capillary	DB-1	60.	820.8	Lubeck and Sutton, 1983	60. m/0.259 mm/1. μm
Capillary	Squalane	70.	825.3	Nabivach and Kirilenko, 1979	N2; Column length: 50. m
Capillary	Squalane	70.	825.4	Nabivach and Kirilenko, 1979	N2; Column length: 50. m
Capillary	Squalane	100.	833.	Dielmann, Schwengers, et al., 1974	Column length: 100. m; Column diameter: 0.25 mm
Capillary	Squalane	60.	823.	Dielmann, Schwengers, et al., 1974	Column length: 100. m; Column diameter: 0.25 mm
Capillary	Squalane	80.	828.	Dielmann, Schwengers, et al., 1974	Column length: 100. m; Column diameter: 0.25 mm
Capillary	Squalane	50.	821.	Rijks and Cramers, 1974	N2; Column length: 100. m; Column diameter: 0.25 mm
Capillary	Squalane	70.	826.	Rijks and Cramers, 1974	N2; Column length: 100. m; Column diameter: 0.25 mm
Capillary	Vacuum Grease Oil (VM-4)	35.	820.	Sidorov, Petrova, et al., 1972
Capillary	Vacuum Grease Oil (VM-4)	45.	823.	Sidorov, Petrova, et al., 1972
Capillary	Vacuum Grease Oil (VM-4)	50.	824.	Sidorov, Petrova, et al., 1972
Capillary	Vacuum Grease Oil (VM-4)	58.	826.	Sidorov, Petrova, et al., 1972
Capillary	Vacuum Grease Oil (VM-4)	68.	829.	Sidorov, Petrova, et al., 1972
Capillary	Squalane	70.	821.1	Dimov and Schopov, 1971	Column length: 100. m; Column diameter: 0.25 mm
Packed	Vacuum Grease Oil (VM-4)	35.	820.	Sidorov, Ivanova, et al., 1971
Packed	SE-30	130.	846.	Mitra and Saha, 1970	N2, Chromosorb W; Column length: 6.1 m
Packed	Squalane	27.	816.	Hively and Hinton, 1968	He, Chromosorb P; Column length: 15. m; Column diameter: 0.25 mm
Packed	Squalane	49.	821.	Hively and Hinton, 1968	He, Chromosorb P; Column length: 15. m; Column diameter: 0.25 mm
Packed	Squalane	67.	826.	Hively and Hinton, 1968	He, Chromosorb P; Column length: 15. m; Column diameter: 0.25 mm
Packed	Squalane	86.	830.	Hively and Hinton, 1968	He, Chromosorb P; Column length: 15. m; Column diameter: 0.25 mm

Kovats' RI, non-polar column, temperature ramp

View large format table.

Column type	Active phase	I	Reference	Comment
Capillary	Apiezon L	837.	Louis, 1971	N2, 1. K/min; Column length: 50. m; Column diameter: 0.25 mm; T_start: 60. C

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

View large format table.

Column type	Active phase	I	Reference	Comment
Capillary	Petrocol DH	820.6	Censullo, Jones, et al., 2003	50. m/0.25 mm/0.5 μm, He, 35. C @ 10. min, 3. K/min, 200. C @ 10. min
Capillary	SPB-1	815.95	LECO Corporation, 2003	30. m/0.25 mm/0.25 μm, 40. C @ 2. min, 10. K/min, 250. C @ 2. min
Capillary	DB-5	827.0	Xu, van Stee, et al., 2003	30. m/0.25 mm/1. μm, He, 2.5 K/min; T_start: 50. C; T_end: 200. C
Capillary	OV-101	818.9	Yin, Liu, et al., 2001	N2, 1. K/min; Column length: 80. m; Column diameter: 0.22 mm; T_start: 30. C; T_end: 130. C
Capillary	Petrocol DH	817.	White, Hackett, et al., 1992	100. m/0.25 mm/0.5 μm, He, 1. K/min; T_start: 30. C; T_end: 220. C

Normal alkane RI, non-polar column, isothermal

View large format table.

Column type	Active phase	Temperature (C)	I	Reference	Comment
Capillary	Squalane	100.	832.	Krupcik, Cellar, et al., 1986, 2	Column length: 180. m; Column diameter: 0.25 mm
Capillary	Squalane	40.	817.	Krupcik, Cellar, et al., 1986, 2	Column length: 180. m; Column diameter: 0.25 mm
Capillary	Squalane	70.	825.	Krupcik, Cellar, et al., 1986, 2	Column length: 180. m; Column diameter: 0.25 mm
Capillary	OV-101	50.	816.	Wu and Lu, 1984
Capillary	OV-101	70.	822.	Wu and Lu, 1984

Normal alkane RI, non-polar column, temperature ramp

View large format table.

Column type	Active phase	I	Reference	Comment
Capillary	Polydimethyl siloxane: CP-Sil 5 CB	790.	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	PONA	822.	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	Squalane	821.3	Krupcik, Cellar, et al., 1986	0.1 K/min; Column length: 100. m; Column diameter: 0.25 mm
Capillary	Squalane	823.2	Krupcik, Cellar, et al., 1986	0.2 K/min; Column length: 100. m; Column diameter: 0.25 mm
Capillary	Squalane	826.0	Krupcik, Cellar, et al., 1986	0.4 K/min; Column length: 100. m; Column diameter: 0.25 mm
Capillary	Squalane	828.1	Krupcik, Cellar, et al., 1986	0.6 K/min; Column length: 100. m; Column diameter: 0.25 mm
Capillary	Squalane	829.8	Krupcik, Cellar, et al., 1986	0.8 K/min; Column length: 100. m; Column diameter: 0.25 mm
Capillary	Squalane	831.3	Krupcik, Cellar, et al., 1986	1. K/min; Column length: 100. m; Column diameter: 0.25 mm
Capillary	Squalane	820.	Krupcik, Cellar, et al., 1986, 2	0.1 K/min; Column length: 180. m; Column diameter: 0.25 mm; T_start: 40. C
Capillary	Squalane	822.	Krupcik, Cellar, et al., 1986, 2	0.2 K/min; Column length: 180. m; Column diameter: 0.25 mm; T_start: 40. C
Capillary	Squalane	825.	Krupcik, Cellar, et al., 1986, 2	0.4 K/min; Column length: 180. m; Column diameter: 0.25 mm; T_start: 40. C
Capillary	Squalane	827.	Krupcik, Cellar, et al., 1986, 2	0.6 K/min; Column length: 180. m; Column diameter: 0.25 mm; T_start: 40. C
Capillary	Squalane	829.	Krupcik, Cellar, et al., 1986, 2	0.8 K/min; Column length: 180. m; Column diameter: 0.25 mm; T_start: 40. C
Capillary	Squalane	831.	Krupcik, Cellar, et al., 1986, 2	1.0 K/min; Column length: 180. m; Column diameter: 0.25 mm; T_start: 40. C

References

Go To: Top, Condensed phase thermochemistry data, Phase change data, Gas Chromatography, Notes

Good, 1971
Good, W.D., The enthalpies of combustion and formation of n-propylcyclopentane and five methylethylcyclopentanes, J. Chem. Thermodyn., 1971, 3, 97-103. [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]

Osborn and Douslin, 1974
Osborn, Ann G.; Douslin, Donald R., Vapor-pressure relations for 15 hydrocarbons, J. Chem. Eng. Data, 1974, 19, 2, 114-117, https://doi.org/10.1021/je60061a022 . [all data]

Forziati, Norris, et al., 1949
Forziati, Alphonse F.; Norris, William R.; Rossini, Frederick D., Vapor pressures and boiling points of sixty API-NBS hydrocarbons, J. RES. NATL. BUR. STAN., 1949, 43, 6, 555-17, https://doi.org/10.6028/jres.043.050 . [all data]

Forziati, Norris, et al., 1949, 2
Forziati, A.F.; Norris, W.R.; Rossini, F.D., Vapor Pressures and Boiling Points of Sixty API-NBS Hydrocarbons, J. Res. Natl. Bur. Stand. (U.S.), 1949, 43, 6, 555-563, https://doi.org/10.6028/jres.043.050 . [all data]

Lunskii and Paizanskaya, 1988
Lunskii, M.Kh.; Paizanskaya, I.L., Identification of hydrocarbons C₁-C₉ of petrol fractions of oils and condensates in the use of capillary columns with dinonylphthalate, Zh. Anal. Khim., 1988, 43, 127-135. [all data]

Krupcik, Cellar, et al., 1986
Krupcik, J.; Cellar, P.; Repka, D.; Garaj, J.; Guiochon, G., Use of Kováts retention indices for characterization of solutes in linear temperature-programmed capillary gas-liquid chromatography, J. Chromatogr., 1986, 351, 111-121, https://doi.org/10.1016/S0021-9673(01)83477-4 . [all data]

Lubeck and Sutton, 1983
Lubeck, A.J.; Sutton, DL., Kovats retention indices of selected hydrocarbons through C₁₀ on bonded phase fused silica capillaries, J. Hi. Res. Chromatogr. Chromatogr. Comm., 1983, 6, 6, 328-332, https://doi.org/10.1002/jhrc.1240060612 . [all data]

Nabivach and Kirilenko, 1979
Nabivach, V.M.; Kirilenko, A.V., The use of retention indices for identifying the components of crude benzene, Solid Fuel Chem. (Engl. Transl.), 1979, 13, 3, 82-87. [all data]

Dielmann, Schwengers, et al., 1974
Dielmann, G.; Schwengers, D.; Schomburg, G., Gas-chromatographische Retentionsdaten und Strukture chemischer Verbindungen Gesättigte und ungesättigte alkylsubstituierte Cyclopentane und Methylcyclopentane, Chromatographia, 1974, 7, 5, 215-224, https://doi.org/10.1007/BF02321771 . [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]

Sidorov, Petrova, et al., 1972
Sidorov, R.I.; Petrova, V.I.; Ivanova, M.P., Qualitative analysis of wide-boiling fraction C5-C10 with capillary chromatography in Processes in chromatographic columns. Vol.17, 1972, 14-25. [all data]

Dimov and Schopov, 1971
Dimov, N.; Schopov, D., Empirische korrektion der physikalisch-chemischen retentionsindexe von kohlenwasserstoffen auf squalan, J. Chromatogr., 1971, 63, 223-228, https://doi.org/10.1016/S0021-9673(01)85634-X . [all data]

Sidorov, Ivanova, et al., 1971
Sidorov, R.I.; Ivanova, M.P.; Petrova, V.I., Temperature dependence of cycloalkane's retention and its using in identification of structure, Gazovaya Khromatografiya, 1971, 15, 18-26. [all data]

Mitra and Saha, 1970
Mitra, G.D.; Saha, N.C., Determination of Retention Indices of Saturated Hydrocarbons by Graphical Methods, J. Chromatogr. Sci., 1970, 8, 2, 95-102, https://doi.org/10.1093/chromsci/8.2.95 . [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]

Louis, 1971
Louis, R., Kovats-index-tafeln zur gaschromatographischen analyse von kohlenwasserstoffgemischen, Erdoel Kohle Erdgas Petrochem., 1971, 24, 2, 88-94. [all data]

Censullo, Jones, et al., 2003
Censullo, A.C.; Jones, D.R.; Wills, M.T., Speciation of the volatile organic compounds (VOCs) in solventborne aerosol coatings by solid phase microextraction-gas chromatography, J. Coat. Technol., 2003, 75, 936, 47-53, https://doi.org/10.1007/BF02697922 . [all data]

LECO Corporation, 2003
LECO Corporation, Determination of hydrocarbon components in petroleum naphthas, 2003, retrieved from http://www.leco.org/customersupport/apps/separationscience/-190.pdf. [all data]

Xu, van Stee, et al., 2003
Xu, X.; van Stee, L.L.P.; Williams, J.; Beens, J.; Adahchour, M.; Vreuls, R.J.J.; Brinkman, U.A.Th.; Lelieveld, J., Comprehensive two-dimensional gas chromatography (GC×GC) measurements of volatile organic compounds in the atmosphere, Atmos. Chem. Phys., 2003, 3, 3, 665-682, https://doi.org/10.5194/acp-3-665-2003 . [all data]

Yin, Liu, et al., 2001
Yin, C.; Liu, W.; Li, Z.; Pan, Z.; Lin, T.; Zhang, M., Chemometrics to chemical modeling: structural coding in hydrocarbons and retention indices of gas chromatography, J. Sep. Sci., 2001, 24, 3, 213-220, https://doi.org/10.1002/1615-9314(20010301)24:3<213::AID-JSSC213>3.0.CO;2-4 . [all data]

White, Hackett, et al., 1992
White, C.M.; Hackett, J.; Anderson, R.R.; Kail, S.; Spock, P.S., Linear temperature programmed retention indices of gasoline range hydrocarbons and chlorinated hydrocarbons on cross-linked polydimethylsiloxane, J. Hi. Res. Chromatogr., 1992, 15, 2, 105-120, https://doi.org/10.1002/jhrc.1240150211 . [all data]

Krupcik, Cellar, et al., 1986, 2
Krupcik, J.; Cellar, P.; Repka, D., Analyza cyklickych a aromatickych uhlovodnikov s poctom uhlikovych atomov 8 kapilarnou plynovou chromatografiou, Ropa a Uhlie, 1986, 28, 8, 485-495. [all data]

Wu and Lu, 1984
Wu, J.; Lu, W., Kovats indices of C4-C10 hydrocarbons in apolar quartz capillary OV-101, Chin. J. Chromatogr., 1984, 1, 1, 11-17. [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]

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]

Notes

Go To: Top, Condensed phase thermochemistry data, Phase change data, Gas Chromatography, References

Symbols used in this document:

T_boil	Boiling point
T_fus	Fusion (melting) point
Δ_cH°_liquid	Enthalpy of combustion of liquid at standard conditions
Δ_fH°_liquid	Enthalpy of formation of liquid at standard conditions
Δ_vapH	Enthalpy of vaporization
Δ_vapH°	Enthalpy of vaporization at standard conditions

Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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