Cyclopentane

• Formula: C₅H₁₀
• Molecular weight: 70.1329
• IUPAC Standard InChI: InChI=1S/C5H10/c1-2-4-5-3-1/h1-5H2 Copy

  
• IUPAC Standard InChIKey: RGSFGYAAUTVSQA-UHFFFAOYSA-N Copy
• CAS Registry Number: 287-92-3
• 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.
• Other names: Pentamethylene; UN 1146
• Permanent link for this species. Use this link for bookmarking this species for future reference.
• Information on this page:
  • Gas phase thermochemistry data
  • Phase change data
  • Reaction thermochemistry data
  • Mass spectrum (electron ionization)
  • Gas Chromatography
  • References
  • Notes
• Other data available:
  • Condensed phase thermochemistry data
  • Henry's Law data
  • Gas phase ion energetics data
  • IR Spectrum
  • UV/Visible spectrum
• Data at other public NIST sites:
  • Gas Phase Kinetics Database
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• NIST / TRC Web Thermo Tables, professional edition (thermophysical and thermochemical data)

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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
DRB - Donald R. Burgess, Jr.
GT - Glushko Thermocenter, Russian Academy of Sciences, Moscow

Constant pressure heat capacity of gas

Constant pressure heat capacity of gas

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
DRB - Donald R. Burgess, Jr.
DH - Eugene S. Domalski and Elizabeth D. Hearing

Enthalpy of vaporization

Enthalpy of vaporization

Δ_vapH = A exp(-βT_r) (1 − T_r)^β
    Δ_vapH = Enthalpy of vaporization (at saturation pressure) (kJ/mol)
    T_r = reduced temperature (T / T_c)

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Entropy of vaporization

Antoine Equation Parameters

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

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Enthalpy of sublimation

Enthalpy of fusion

Enthalpy of phase transition

Entropy of phase transition

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
B - John E. Bartmess

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 + C₅H₈ = C₅H₁₀

C₅H₉^- +  =

By formula: C₅H₉^- + H⁺ = C₅H₁₀

 +  =

By formula: H₂ + C₅H₈ = C₅H₁₀

2 +  =

By formula: 2H₂ + C₅H₆ = C₅H₁₀

2 +  =

By formula: 2H₂ + C₅H₆ = C₅H₁₀

 +  = 2 + 

By formula: C₅H₁₀ + I₂ = 2HI + C₅H₈

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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Additional Data

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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Kovats' RI, non-polar column, temperature ramp

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

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Kovats' RI, polar column, isothermal

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

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

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Normal alkane RI, non-polar column, isothermal

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Normal alkane RI, non-polar column, temperature ramp

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

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References

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

McCullough, Pennington, et al., 1959
McCullough, J.P.; Pennington, R.E.; Smith, J.C.; Hossenlopp, I.A.; Waddington, G., Thermodynamics of cyclopentane, methylcyclopentane and 1,cis-3-dimethylcyclopentane: Verification of the concept of pseudorotation, J. Am. Chem. Soc., 1959, 81, 5880-5883. [all data]

Spitzer and Huffman, 1947
Spitzer, R.; Huffman, H.M., The heats of combustion of cyclopentane, cyclohexane, cycloheptane and cyclooctane, J. Am. Chem. Soc., 1947, 69, 211-213. [all data]

Prosen, Johnson, et al., 1946
Prosen, E.J.; Johnson, W.H.; Rossini, F.D., Heats of formation and combustion of the normal alkylcyclopentanes and cyclohexanes and the increment per CH₂ group for several homologous series of hydrocarbons, J. Res. NBS, 1946, 37, 51-56. [all data]

Dorofeeva O.V., 1986
Dorofeeva O.V., Thermodynamic properties of twenty-one monocyclic hydrocarbons, J. Phys. Chem. Ref. Data, 1986, 15, 437-464. [all data]

Kilpatrick J.E., 1947
Kilpatrick J.E., The thermodynamics and molecular structure of cyclopentane, J. Am. Chem. Soc., 1947, 69, 2483-2488. [all data]

McCullough J.P., 1959
McCullough J.P., Thermodynamics of cyclopentane, methylcyclopentane and 1,cis-3-dimethylcyclopentane: verification of the concept of pseudorotation, J. Am. Chem. Soc., 1959, 81, 5880-5883. [all data]

Sundaram S., 1963
Sundaram S., Thermodynamic functions of some propellants, Z. Phys. Chem. (Frankfurt), 1963, 36, 376-377. [all data]

Spitzer R., 1946
Spitzer R., The heat capacity of gaseous cyclopentane, cyclohexane and methylcyclohexane, J. Am. Chem. Soc., 1946, 68, 2537-2538. [all data]

Douslin and Huffman, 1946
Douslin, D.R.; Huffman, H.M., The heat capacities, heats of transition, heats of fusion and entropies of cyclopentane, methylcyclopentane and methylcyclohexane., J. Am. Chem. Soc., 1946, 68, 173. [all data]

Aston, Finke, et al., 1943
Aston, J.G.; Finke, H.L.; Schumann, S.C., The heat capacity and entropy, heats of transition, fusion and vaporization and the vapor pressures of cyclopentane. Evidence for a non-planar structure, J. Am. Chem. Soc., 1943, 65, 341. [all data]

Jacobs and Parks, 1934
Jacobs, C.J.; Parks, G.S., Thermal data on organic compounds. XIV. Some heat capacity, entropy and free energy data for cyclic substances, J. Am. Chem. Soc., 1934, 56, 1513-17. [all data]

Daubert, 1996
Daubert, T.E., Vapor-Liquid Critical Properties of Elements and Compounds. 5. Branched Alkanes and Cycloalkanes, J. Chem. Eng. Data, 1996, 41, 365-372. [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]

Kudchadker, Alani, et al., 1968
Kudchadker, A.P.; Alani, G.H.; Zwolinski, B.J., The Critical Constants of Organic Substances, Chem. Rev., 1968, 68, 659. [all data]

Ambrose and Grant, 1957
Ambrose, D.; Grant, D.G., The Critical Temperatures of Some Hydrocarbons and Pyridine Bases, Trans. Faraday Soc., 1957, 53, 771. [all data]

Kay, 1947
Kay, W.B., Vapor Pressures and Saturated Liquid and Vapor DEensities of Cyclopentane, Methylcyclopentane, Ethylcyclopentane, and Methylcyclohexane, J. Am. Chem. Soc., 1947, 69, 1273-7. [all data]

Aston, Fink, et al., 1943
Aston, J.G.; Fink, H.L.; Schumann, S.C., The heat capacity and entropy, heats of transition, fusion and vaporization and the vapor pressures of cyclopentane. Evidence for a non-planar structure, J. Am. Chem. Soc., 1943, 65, 341-346. [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]

Spitzer and Pitzer, 1946
Spitzer, Ralph; Pitzer, Kenneth S., The Heat Capacity of Gaseous Cyclopentane, Cyclohexane and Methylcyclohexane, J. Am. Chem. Soc., 1946, 68, 12, 2537-2538, https://doi.org/10.1021/ja01216a032 . [all data]

Willingham, Taylor, et al., 1945
Willingham, C.B.; Taylor, W.J.; Pignocco, J.M.; Rossini, F.D., Vapor pressures and boiling points of some paraffin, alkylcyclopentane, alkylcyclohexane, and alkylbenzene hydrocarbons, J. RES. NATL. BUR. STAN., 1945, 35, 3, 219-17, https://doi.org/10.6028/jres.035.009 . [all data]

Williamham, Taylor, et al., 1945
Williamham, C.B.; Taylor, W.J.; Pignocco, J.M.; Rossini, F.D., Vapor Pressures and Boiling Points of Some Paraffin, Alkylcyclopentane, Alkylcyclohexane, and Alkylbenzene Hydrocarbons, J. Res. Natl. Bur. Stand. (U.S.), 1945, 35, 3, 219-244, https://doi.org/10.6028/jres.035.009 . [all data]

Bondi, 1963
Bondi, A., Heat of Siblimation of Molecular Crystals: A Catalog of Molecular Structure Increments., J. Chem. Eng. Data, 1963, 8, 3, 371-381, https://doi.org/10.1021/je60018a027 . [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]

Rahm and Gmelin, 1992
Rahm, U.; Gmelin, E., Low temperature microcalorimetry by differential scanning, J. Therm. Anal., 1992, 38(3), 335-344. [all data]

Szasz, Morrison, et al., 1947
Szasz, G.J.; Morrison, J.A.; Pace, E.L.; Aston, J.G., Thermal properties of cyclopentane and its use as a standard substance in low temperature thermal measurements, J. Chem. Phys., 1947, 15, 562-564. [all data]

Douslin and Huffman, 1946, 2
Douslin, D.R.; Huffman, H.M., The heat capacities, heats of transition, heats of fusion and entropies of cyclopentane, methylcyclopentane and methylcylohexane, J. Am. Chem. Soc., 1946, 68, 173-176. [all data]

Jacobs and Parks, 1934, 2
Jacobs, C.J.; Parks, G.S., Thermal data on organic compounds. XIV. Some heat capacity, entropy and free energy data for cyclic substances, J. Am. Chem. Soc., 1934, 56, 1513-1517. [all data]

Allinger, Dodziuk, et al., 1982
Allinger, N.L.; Dodziuk, H.; Rogers, D.W.; Naik, S.N., Heats of hydrogenation and formation of some 5-membered ring compounds by molecular mechanics calculations and direct measurements, Tetrahedron, 1982, 38, 1593-1597. [all data]

Roth and Lennartz, 1980
Roth, W.R.; Lennartz, H.W., Heats of hydrogenation. I. Determination of heats of hydrogenation with an isothermal titration calorimeter, Chem. Ber., 1980, 113, 1806-1817. [all data]

Turner, Jarrett, et al., 1973
Turner, R.B.; Jarrett, A.D.; Goebel, P.; Mallon, B.J., Heats of hydrogenation. 9. Cyclic acetylenes and some miscellaneous olefins, J. Am. Chem. Soc., 1973, 95, 790-792. [all data]

Rogers and McLafferty, 1971
Rogers, D.W.; McLafferty, F.J., A new hydrogen calorimeter. Heats of hydrogenation of allyl and vinyl unsaturation adjacent to a ring, Tetrahedron, 1971, 27, 3765-3775. [all data]

Dolliver, Gresham, et al., 1937
Dolliver, M.a.; Gresham, T.L.; Kistiakowsky, G.B.; Vaughan, W.E., Heats of organic reactions. V. Heats of hydrogenation of various hydrocarbons, J. Am. Chem. Soc., 1937, 59, 831-841. [all data]

Cox and Pilcher, 1970
Cox, J.D.; Pilcher, G., Thermochemistry of Organic and Organometallic Compounds, Academic Press, New York, 1970, 1-636. [all data]

DePuy, Gronert, et al., 1989
DePuy, C.H.; Gronert, S.; Barlow, S.E.; Bierbaum, V.M.; Damrauer, R., The Gas Phase Acidities of the Alkanes, J. Am. Chem. Soc., 1989, 111, 6, 1968, https://doi.org/10.1021/ja00188a003 . [all data]

Peerboom, Rademaker, et al., 1992
Peerboom, R.A.L.; Rademaker, G.J.; Dekoning, L.J.; Nibbering, N.M.M., Stabilization of Cycloalkyl Carbanions in the Gas Phase, Rapid Commun. Mass Spectrom., 1992, 6, 6, 394, https://doi.org/10.1002/rcm.1290060608 . [all data]

Roth, Klarner, et al., 1980
Roth, W.R.; Klarner, F.-G.; Lennartz, H.-W., Heats of hydrogenation. II. Heat of hydrogenation of bicyclo[2.1.0]pent-2-ene, an antiaromatic system, Chem. Ber., 1980, 113, 1806-1818. [all data]

Turner, Goebel, et al., 1968
Turner, R.B.; Goebel, P.; Mallon, B.J.; Doering, W.E.; Coburn, J.F., Jr.; Pomerantz, M., Heats of hydrogenation. VIII. Compounds with three- and four-membered rings, J. Am. Chem. Soc., 1968, 90, 4315-4322. [all data]

Kistiakowsky, Ruhoff, et al., 1936
Kistiakowsky, G.B.; Ruhoff, J.R.; Smith, H.A.; Vaughan, W.E., Heats of organic reactions. IV. Hydrogenation of some dienes and of benzene, J. Am. Chem. Soc., 1936, 58, 146-153. [all data]

Furuyama, Golden, et al., 1970
Furuyama, S.; Golden, D.M.; Benson, S.W., Thermochemistry of cyclopentene and cyclopentadiene from studies of gas-phase equilibria, J. Chem. Thermodyn., 1970, 2, 161-169. [all data]

Kurbatova, Finkelstein, et al., 2004
Kurbatova, S.V.; Finkelstein, E.E.; Kolosova, E.A.; Kartashev, A.V.; Rashkin, S.V., Structural analogy method in studies of adamantanes, J. Struct. Chem., 2004, 45, 1, 144-150, https://doi.org/10.1023/B:JORY.0000041513.82837.4e . [all data]

Dallos, Sisak, et al., 2000
Dallos, A.; Sisak, A.; Kulcsár, Z.; Kováts, E., Pair-wise interactions by gas chromatography VII. Interaction free enthalpies of solutes with secondary alcohol groups, J. Chromatogr. A, 2000, 904, 2, 211-242, https://doi.org/10.1016/S0021-9673(00)00908-0 . [all data]

Skrbic, 1997
Skrbic, B.D., Unified retention concept -- statistical treatment of Kováts retention index, J. Chromatogr. A, 1997, 764, 2, 257-264, https://doi.org/10.1016/S0021-9673(96)00955-7 . [all data]

Aflalaye, Sternberg, et al., 1995
Aflalaye, A.; Sternberg, R.; Raulin, F.; Vidal-Madjar, C., Gas chromatography of Titan's atmosphere. VI. Analysis of low-molecular-mass hydrocarbons and nitriles with BPX5 capillary columns, J. Chromatogr. A, 1995, 708, 2, 283-291, https://doi.org/10.1016/0021-9673(95)00410-O . [all data]

Estel, Mohnke, et al., 1995
Estel, D.; Mohnke; Biermans; Rotzsche, The analysis of C₄-C₁₁ hydrocarbons in naphtha and reformate with a new apolar fused silica column, J. Hi. Res. Chromatogr., 1995, 18, 7, 403-412, https://doi.org/10.1002/jhrc.1240180703 . [all data]

Cha and Lee, 1994
Cha, K.-W.; Lee, D.-J., Prediction of retention indices of various compounds in gas-liquid chromatography, J. Korean Chem. Soc., 1994, 38, 2, 108-120, retrieved from http://journal.kcsnet.or.kr/publi/dh/dh94n2/108.pdf. [all data]

Hilal, Carreira, et al., 1994
Hilal, S.H.; Carreira, L.A.; Karickhoff, S.W.; Melton, C.M., Estimation of Gas-Liquid Chromatographic Retention Times from Molecular Structure, J. Chromatogr. A, 1994, 662, 2, 269-280, https://doi.org/10.1016/0021-9673(94)80515-6 . [all data]

Krupcik, Skacani, et al., 1994
Krupcik, J.; Skacani, I.; Benicka, E.; Sandra, P., Dependence of gas chromatographic retention data of hydrocarbons on the film thickness of the polydimethylsiloxane stationary phase, Collect. Czech. Chem. Commun., 1994, 59, 11, 2390-2396, https://doi.org/10.1135/cccc19942390 . [all data]

Do and Raulin, 1992
Do, L.; Raulin, F., Gas chromatography of Titan's atmosphere. III. Analysis of low-molecular-weight hydrocarbons and nitriles with a CP-Sil-5 CB WCOT capillary column, J. Chromatogr., 1992, 591, 1-2, 297-301, https://doi.org/10.1016/0021-9673(92)80247-R . [all data]

Reddy, Dutoit, et al., 1992
Reddy, K.S.; Dutoit, J.-Cl.; Kovats, E. sz., Pair-wise interactions by gas chromatography. I. Interaction free enthalpies of solutes with non-associated primary alcohol groups, J. Chromatogr., 1992, 609, 1-2, 229-259, https://doi.org/10.1016/0021-9673(92)80167-S . [all data]

Dutoit, 1991
Dutoit, J., Gas chromatographic retention behaviour of some solutes on structurally similar polar and non-polar stationary phases, J. Chromatogr., 1991, 555, 1-2, 191-204, https://doi.org/10.1016/S0021-9673(01)87179-X . [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]

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]

Papazova, Milina, et al., 1988
Papazova, D.; Milina, R.; Dimov, N., Comparative evaluation of retention of hydrocarbons present in the C₅-petroleum fraction of methylsilicone and squalane phases, Chromatographia, 1988, 25, 3, 177-180, https://doi.org/10.1007/BF02316441 . [all data]

Boneva and Dimov, 1986
Boneva, S.; Dimov, N., Unified retention index of hydrocarbons separated on dimethylsilicone OV-101, Chromatographia, 1986, 21, 12, 697-700, https://doi.org/10.1007/BF02313682 . [all data]

Anders, Anders, et al., 1985
Anders, G.; Anders, K.; Engewald, W., Identification of non-branched alkenylcycloalkanes with a terminal double bond from retention index increments, Chromatographia, 1985, 20, 2, 83-86, https://doi.org/10.1007/BF02280602 . [all data]

Chien, Furio, et al., 1983
Chien, C.-F.; Furio, D.L.; Kopecni, M.M.; Laub, R.J., Specific Retention Volumes and Retention Indices of Selected Hydrocarbon Solutes with OV-101 and SP-2100 Polydimethylsiloxane Solvents, J. Hi. Res. Chromatogr. Chromatogr. Comm., 1983, 6, 10, 577-580, https://doi.org/10.1002/jhrc.1240061013 . [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]

Winskowski, 1983
Winskowski, J., Gaschromatographische Identifizierung von Stoffen anhand von Indexziffem und unterschiedlichen Detektoren, Chromatographia, 1983, 17, 3, 160-165, https://doi.org/10.1007/BF02271041 . [all data]

Anders, Scheller, et al., 1982
Anders, G.; Scheller, M.; Schuhler, C.; Struppe, H.G., Zur Vorausberechnung von Bruttoretentioszeiten bei temperaturprogramierter Gaschromatographie mit Hilfe isotherm bestimmter Retentionsindices und einer Anpassung an experimentelle Retentionszeiten, Chromatographia, 1982, 15, 1, 43-47, https://doi.org/10.1007/BF02269039 . [all data]

Bredael, 1982
Bredael, P., Retention indices of hydrocarbons on SE-30, J. Hi. Res. Chromatogr. Chromatogr. Comm., 1982, 5, 6, 325-328, https://doi.org/10.1002/jhrc.1240050610 . [all data]

Johansen and Ettre, 1982
Johansen, N.G.; Ettre, L.S., Retention index values of hydrocarbons on open-tubular columns coated with methylsilicone liquid phases, Chromatographia, 1982, 15, 10, 625-630, https://doi.org/10.1007/BF02279488 . [all data]

Nabivach and Kirilenko, 1980
Nabivach, V.M.; Kirilenko, A.V., Relationship between the gas chromatographic behaviour and the molecular structure of hydrocarbon samples and various stationary phases. Part II. Correlation between the retention index, physicochemical properties and molecular structure, Chromatographia, 1980, 13, 2, 93-100, https://doi.org/10.1007/BF02263060 . [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]

Pacáková and Koslík, 1978
Pacáková, V.; Koslík, V., Capillary reaction gas chromatography. I. Catalytic decomposition of hydrocarbons, Chromatographia, 1978, 11, 5, 266-273, https://doi.org/10.1007/BF02282952 . [all data]

Stopp, Engewald, et al., 1978
Stopp, I.; Engewald, W.; Kühn, H.; Welsch, Th., Molekülstruktur und retentionsverhalten. VIII. Zum gaschromatographischen retentionsverhalten von dicyclopentadienderivaten, J. Chromatogr., 1978, 147, 21-30, https://doi.org/10.1016/S0021-9673(00)85113-4 . [all data]

Riedo, Fritz, et al., 1976
Riedo, F.; Fritz, D.; Tarján, G.; Kováts, E.Sz., A tailor-made C₈₇ hydrocarbon as a possible non-polar standard stationary phase for gas chromatography, J. Chromatogr., 1976, 126, 63-83, https://doi.org/10.1016/S0021-9673(01)84063-2 . [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]

Besson and Gäumann, 1973
Besson, R.; Gäumann, T., Indices de rétention de cycloalcanes, cycloalcènes, bicycloalkyles, cycloalkyl-cycloalcényles et bicycloalcényles en chromatographie en phase gazeuse, Helv. Chim. Acta, 1973, 56, 3, 1159-1164, https://doi.org/10.1002/hlca.19730560339 . [all data]

Pacáková, Hoch, et al., 1973
Pacáková, V.; Hoch, K.; Smolková, E., The Effect of Instrumentation on the Precision of Retention Indexes, Chromatographia, 1973, 6, 7, 320-324, https://doi.org/10.1007/BF02269334 . [all data]

Agrawal, Tesarík, et al., 1972
Agrawal, B.B.; Tesarík, K.; Janák, J., Gas chromatographic characterization of sulphur compounds in the 93-162° gasoline cut from Romashkino crude oil using Kováts retention indices, J. Chromatogr., 1972, 65, 1, 207-215, https://doi.org/10.1016/S0021-9673(00)86933-2 . [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]

Robinson and Odell, 1971
Robinson, P.G.; Odell, A.L., A system of standard retention indices and its uses. The characterisation of stationary phases and the prediction of retention indices, J. Chromatogr., 1971, 57, 1-10, https://doi.org/10.1016/0021-9673(71)80001-8 . [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]

Cramers, Rijks, et al., 1970
Cramers, C.A.; Rijks, J.A.; Pacáková, V.; de Andrade, I.R., The application of precision gas chromatography to the identification of types of hydrocarbons, J. Chromatogr., 1970, 51, 13-21, https://doi.org/10.1016/S0021-9673(01)96835-9 . [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]

Evans, 1966
Evans, M.B., Retention indices of solutes on squalane, dinonyl phthalate, and polyethylene glycol 400, J. Gas Chromatogr., 1966, 4, 1, 1-3, https://doi.org/10.1093/chromsci/4.1.1 . [all data]

Schomburg, 1966
Schomburg, G., Gaschromatographische Retentionsdaten und struktur chemischer verbindungen. III. Alkylverzweigte und ungesättigte cyclische Kohlenwasserstoffe, J. Chromatogr., 1966, 23, 18-41, https://doi.org/10.1016/S0021-9673(01)98653-4 . [all data]

Antheaume and Guiochon, 1965
Antheaume, J.; Guiochon, G., Application de la chromatographie en phase gazeuse à l'étude de la composition des fractions moyennes d'un brut pétrolier, Bull. Soc. Chim. Fr., 1965, 2, 298-307. [all data]

Schomburg, 1964
Schomburg, G., Gas-Chromatographische Retentionsdaten und Struktur Chemischer Verbindungen. I. Verzweigte Aliphatische und Alicyclische Carbonsäure-Methylester, J. Chromatogr., 1964, 14, 157-177, https://doi.org/10.1016/S0021-9673(00)86608-X . [all data]

Wehrli and Kováts, 1959
Wehrli, A.; Kováts, E., Gas-chromatographische Charakterisierung ogranischer Verbindungen. Teil 3: Berechnung der Retentionsindices aliphatischer, alicyclischer und aromatischer Verbindungen, Helv. Chim. Acta, 1959, 7, 7, 2709-2736, https://doi.org/10.1002/hlca.19590420745 . [all data]

Hayes and Pitzer, 1982
Hayes, P.C., Jr.; Pitzer, E.W., Characterizing petroleum- and shale-derived jet fuel distillates via temperature-programmed Kováts indices, J. Chromatogr., 1982, 253, 179-198, https://doi.org/10.1016/S0021-9673(01)88376-X . [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]

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]

Hoekman, 1993
Hoekman, S.K., Improved gas chromatography procedure for speciated hydrocarbon measurements of vehicle emissions, J. Chromatogr., 1993, 639, 2, 239-253, https://doi.org/10.1016/0021-9673(93)80260-F . [all data]

Anderson, Jurel, et al., 1973
Anderson, A.; Jurel, S.; Shymanska, M.; Golender, L., Gas-liquid chromatography of some aliphatic and heterocyclic mono- and pollyfunctional amines. VII. Retention indices of amines in some polar and unpolar stationary phases, Latv. PSR Zinat. Akad. Vestis Kim. Ser., 1973, 1, 51-63. [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]

Subramaniam, Bochniak, et al., 1994
Subramaniam, B.; Bochniak, D.; Snavely, K., Fischer-Tropsch synthesis in supercritical reaction media, Lawrence Department of Chemical and Petroleum Engineering (DOE/PC/92532--T7), United States Department of Energy, Pittsburgh, PA, 1994, 8, retrieved from http://www.NTIS.gov. [all data]

White, Douglas, et al., 1992
White, C.M.; Douglas, L.J.; Hackett, J.P.; Anderson, R.R., Characterization of synthetic gasoline from the chloromethane-zeolite reaction, Energy Fuels, 1992, 6, 1, 76-82, https://doi.org/10.1021/ef00031a012 . [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]

Hayes and Pitzer, 1981
Hayes, P.C., Jr.; Pitzer, E.W., Kovats indices as a tool in characterizing hydrocarbon fuels in temperature programmed glass capillary gas chromatography. Part 1. Qualitative identification, Inhouse rpt. for Air Force Wright Aeronautical Labs., Air Force Wright Aeronautical Labs., Wright-Patterson AFB, Ohio, 1981, 75. [all data]

Peng, 2000
Peng, C.T., Prediction of retention indices. V. Influence of electronic effects and column polarity on retention index, J. Chromatogr. A, 2000, 903, 1-2, 117-143, https://doi.org/10.1016/S0021-9673(00)00901-8 . [all data]

Peng, Ding, et al., 1988
Peng, C.T.; Ding, S.F.; Hua, R.L.; Yang, Z.C., Prediction of Retention Indexes I. Structure-Retention Index Relationship on Apolar Columns, J. Chromatogr., 1988, 436, 137-172, https://doi.org/10.1016/S0021-9673(00)94575-8 . [all data]

Li and Deng, 1998
Li, H.; Deng, C., Qualitative analysis of light components of gasoline cracking using Kovats retention indices, J. Instrumental Analysis, 1998, 17, 1, 67-69. [all data]

Xieyun, Maoqi, et al., 1996
Xieyun, H.; Maoqi, C.; Shiyan, Y., Gas Chromatographic analysis during the process of heptaldehyde production using 1-hexene, Chin. J. Chromatogr., 1996, 14, 4, 291-293. [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]

Dufka, Malinsky, et al., 1971
Dufka, O.; Malinsky, J.; Vladyka, J., Sorpcni materialy pro plynovou chromatographii - III, Chemicky promysl., 1971, 21/46, 9, 459-463. [all data]

Vigdergauz and Martynov, 1971
Vigdergauz, M.S.; Martynov, A.A., Some applications of the gas chromatographic linear retention indices, Chromatographia, 1971, 4, 10, 463-467, https://doi.org/10.1007/BF02268816 . [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]

Health Safety Executive, 2000
Health Safety Executive, MDHS 96 Volatile organic compounds in air - Laboratory method using pumed solid sorbent tubes, solvent desorption and gas chromatography in Methods for the Determination of Hazardous Substances (MDHS) guidance, Crown, Colegate, Norwich, 2000, 1-24, retrieved from http://www.hse.gov.uk/pubns/mdhs/pdfs/mdhs96.pdf. [all data]

Shoenmakers, Oomen, et al., 2000
Shoenmakers, P.J.; Oomen, J.L.M.M.; Blomberg, J.; Genuit, W.; van Velzen, G., Comparison of comprehensive two-dimensional gas chromatography and gas chromatography-mass spectrometry for the characterization of complex hydrocarbon mixtures, J. Chromatogr. A, 2000, 892, 1-2, 29-46, https://doi.org/10.1016/S0021-9673(00)00744-5 . [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]

Guan, Li, et al., 1995
Guan, Y.; Li, L.; Zhou, L., Live retention database for compound identification in capillary gas chromatography, Chin. J. Chromatogr., 1995, 13, 5, 851-857. [all data]

Chen, 2008
Chen, H.-F., Quantitative prediction of gas chromatography retention indices with support vector machines, radial basis neutral networks and multiple linear regression, Anal. Chim. Acta, 2008, 609, 1, 24-36, https://doi.org/10.1016/j.aca.2008.01.003 . [all data]

Blunden, Aneja, et al., 2005
Blunden, J.; Aneja, V.P.; Lonneman, W.A., Characterization of non-methane volatile organic compounds at swine facilities in eastern North Carolina, Atm. Environ., 2005, 39, 36, 6707-6718, https://doi.org/10.1016/j.atmosenv.2005.03.053 . [all data]

Finkelstein, Kurbatova, et al., 2002
Finkelstein, E.E.; Kurbatova, S.V.; Kolosova, E.A., Study of biological activity of structure analogies of adamantane, Proc. Samara State Univ., 2002, 26, 4, 121-128. [all data]

Perkin Elmer Instruments, 2002
Perkin Elmer Instruments, Detailed hydrocarbon analysis (DHAX) Model 4015, 2002, retrieved from http://www.perkinelmer.com/instruments. [all data]

Zhu and Wang, 2001
Zhu, X.; Wang, W., The relationship between partition coefficients of hydrocarbons and their retention indices, Acta Scientific Circumstantiae, 2001, 21, 5, 631-633. [all data]

Zenkevich, 2000
Zenkevich, I.G., Mutual Correlation between Gas Chromatographic Retention Indices of Unsaturated and Saturated Hydrocarbons found by Molecular Dynamics, Z. Anal. Chem., 2000, 55, 10, 1091-1097. [all data]

Spieksma, 1999
Spieksma, W., Determination of vapor liquid equilibrium from the Kovats retention index on dimethylsilicone using the Wilson mixing tool, J. Hi. Res. Chromatogr., 1999, 22, 10, 565-588, https://doi.org/10.1002/(SICI)1521-4168(19991001)22:10<565::AID-JHRC565>3.0.CO;2-2 . [all data]

Zenkevich, 1998
Zenkevich, I.G., Reciprocally Unambiguous Conformity Between GC Retention Indices and Boiling Points within Two- and Multidimensional Taxonomic Groups of Organic Compounds, J. Hi. Res. Chromatogr., 1998, 21, 10, 565-568, https://doi.org/10.1002/(SICI)1521-4168(19981001)21:10<565::AID-JHRC565>3.0.CO;2-6 . [all data]

Zenkevich, 1996
Zenkevich, I.G., Informational Maitenance of Gas Chromatographic Identification of Organic Compounds in Ecoanalytical Investigations, Z. Anal. Chem., 1996, 51, 11, 1140-1148. [all data]

Ciccioli, Cecinato, et al., 1994
Ciccioli, P.; Cecinato, A.; Brancaleoni, E.; Brachetti, A.; Frattoni, M.; Sparapani, R., Composition and Distribution of Polar and Non-Polar VOCs in Urban, Rural, Forest and Remote Areas, Eur Commission EUR, 1994, 549-568. [all data]

Skrbic and Cvejanov, 1993
Skrbic, B.D.; Cvejanov, J.Dj., Correlation of unified retention indices for OV-101 and squalane, Chromatographia, 1993, 35, 1/2, 109-110, https://doi.org/10.1007/BF02278566 . [all data]

Strete, Ruprah, et al., 1992
Strete, P.J.; Ruprah, M.; Ramsey, J.D.; Flanagan, R.J., Detection and identification of volatile substances by headspace capillary gas chromatography to aid the diagnosis of acute poisoning, Analyst, 1992, 117, 7, 1111-1127, https://doi.org/10.1039/an9921701111 . [all data]

van Langenhove and Schamp, 1986
van Langenhove, H.; Schamp, N., Identification of Volatiles in the Head Space of Acid-Treated Phosphate Rock by Gas Chromatography-Mass Spectromety, J. Chromatogr., 1986, 351, 65-75, https://doi.org/10.1016/S0021-9673(01)83473-7 . [all data]

Waggott and Davies, 1984
Waggott, A.; Davies, I.W., Identification of organic pollutants using linear temperature programmed retention indices (LTPRIs) - Part II, 1984, retrieved from http://dwi.defra.gov.uk/research/completed-research/reports/dwi0383.pdf. [all data]

Robinson and Odell, 1971, 2
Robinson, P.G.; Odell, A.L., Comparison of isothermal and non-linear temperature programmed gas chromatography. The temperature dependence of the retention indices of a number of hydrocarbons on squalane and SE-30, J. Chromatogr., 1971, 57, 11-17, https://doi.org/10.1016/0021-9673(71)80002-X . [all data]

Notes

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

• Symbols used in this document:
  

  Cp,gas	Constant pressure heat capacity of gas
  Pc	Critical pressure
  Tboil	Boiling point
  Tc	Critical temperature
  Tfus	Fusion (melting) point
  Ttriple	Triple point temperature
  Vc	Critical volume
  ΔHtrs	Enthalpy of phase transition
  ΔStrs	Entropy of phase transition
  ΔfH°gas	Enthalpy of formation of gas at standard conditions
  ΔfusH	Enthalpy of fusion
  ΔrG°	Free energy of reaction at standard conditions
  ΔrH°	Enthalpy of reaction at standard conditions
  ΔsubH	Enthalpy of sublimation
  ΔvapH	Enthalpy of vaporization
  ΔvapH°	Enthalpy of vaporization at standard conditions
  ΔvapS	Entropy of vaporization
  ρc	Critical density

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