Cyclododecane

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

Quantity Value Units Method Reference Comment
Δcgas-1777.kcal/molCcbSmith and Easley, 1963Corresponding Δfgas = -172. kcal/mol (simple calculation by NIST; no Washburn corrections)

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
Δcsolid-1840.42kcal/molCcbGollis, Belenyessy, et al., 1962Corresponding Δfsolid = -107.97 kcal/mol (simple calculation by NIST; no Washburn corrections)
Δcsolid-1875.10 ± 0.31kcal/molCcbCoops, Van Kamp, et al., 1960Reanalyzed by Cox and Pilcher, 1970, Original value = -1875.0 ± 0.31 kcal/mol; Corresponding Δfsolid = -73.298 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:
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
AC - William E. Acree, Jr., James S. Chickos
CAL - James S. Chickos, William E. Acree, Jr., Joel F. Liebman, Students of Chem 202 (Introduction to the Literature of Chemistry), University of Missouri -- St. Louis

Quantity Value Units Method Reference Comment
Tfus333.8KN/ADrotloff and Moller, 1987Crystal phase 1 phase; Uncertainty assigned by TRC = 0.3 K; TRC
Tfus332.5KN/AMueller, Padeken, et al., 1965Uncertainty assigned by TRC = 1. K; TRC
Tfus316.KN/AGollis, Belenyessy, et al., 1962, 2Uncertainty assigned by TRC = 1.66 K; TRC
Quantity Value Units Method Reference Comment
Δvap15.1kcal/molCGCChickos, Hesse, et al., 1998AC
Δvap15.0kcal/molCGCChickos, Hosseini, et al., 1995Based on data from 403. to 453. K.; AC
Quantity Value Units Method Reference Comment
Δsub18.2kcal/molCGC-DSCChickos, Hesse, et al., 1998AC

Enthalpy of vaporization

ΔvapH (kcal/mol) Temperature (K) Method Reference Comment
12.6401.A,EBStephenson and Malanowski, 1987Based on data from 386. to 441. K. See also Meyer and Hotz, 1976.; AC
11.9455.A,EBStephenson and Malanowski, 1987Based on data from 440. to 529. K. See also Meyer and Hotz, 1976.; AC

Enthalpy of fusion

ΔfusH (kcal/mol) Temperature (K) Reference Comment
3.54333.8Drotloff and Möller, 1987AC

Entropy of fusion

ΔfusS (cal/mol*K) Temperature (K) Reference Comment
0.722199.Drotloff and Moller, 1987CAL
10.60333.8

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

Cyclododecyne + 2Hydrogen = Cyclododecane

By formula: C12H20 + 2H2 = C12H24

Quantity Value Units Method Reference Comment
Δr-61.75 ± 0.40kcal/molChydTurner, Jarrett, et al., 1973liquid phase; solvent: Acetic acid
Δr-61.7kcal/molChydSicher, Svoboda, et al., 1968liquid phase; solvent: Acetic acid

Hydrogen + Cyclododecene, (E)- = Cyclododecane

By formula: H2 + C12H22 = C12H24

Quantity Value Units Method Reference Comment
Δr-26.8kcal/molChydSicher, Svoboda, et al., 1968liquid phase; solvent: Acetic acid

Cyclododecene, (Z)- + Hydrogen = Cyclododecane

By formula: C12H22 + H2 = C12H24

Quantity Value Units Method Reference Comment
Δr-26.3kcal/molChydSicher, Svoboda, et al., 1968liquid 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
9.72 ± 0.03PIGolubitskii, Kulikov, et al., 1979LLK
10.04 ± 0.05EIPuttemans, 1974LLK

IR Spectrum

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Data compiled by: Coblentz Society, Inc.

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


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.
Origin Japan AIST/NIMC Database- Spectrum MS-NW-3626
NIST MS number 229170

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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

View large format table.

Column type Active phase Temperature (C) I Reference Comment
CapillaryOV-1150.1338.3Rudenko and Rudenko, 2005He; Column diameter: 0.25 mm
CapillaryOV-1170.1351.6Rudenko and Rudenko, 2005He; Column diameter: 0.25 mm
CapillaryOV-1190.1372.4Rudenko and Rudenko, 2005He; Column diameter: 0.25 mm
CapillaryOV-1150.1338.3Rudenko and Rudenko, 2000He; Column diameter: 0.25 mm
CapillaryOV-1170.1351.6Rudenko and Rudenko, 2000He; Column diameter: 0.25 mm
CapillaryOV-1190.1372.4Rudenko and Rudenko, 2000He; Column diameter: 0.25 mm
CapillaryMethyl Silicone160.1360.Boneva and Balbolov, 199350. m/0.25 mm/1.0 μm, N2
CapillaryMethyl Silicone170.1370.Boneva and Balbolov, 199350. m/0.25 mm/1.0 μm, N2
CapillaryMethyl Silicone180.1378.Boneva and Balbolov, 199350. m/0.25 mm/1.0 μm, N2
CapillaryOV-1100.1323.7Engewald, Billing, et al., 1987Column length: 50. m; Column diameter: 0.3 mm
CapillarySqualane120.1326.Engewald, Epsch, et al., 1974N2; Column length: 100. m; Column diameter: 0.23 mm
CapillarySqualane120.1330.Schomburg, 1967Ar; Column length: 100. m
CapillarySqualane120.1325.Schomburg, 1966 
PackedApiezon L130.1384.Wehrli and Kováts, 1959Celite; Column length: 2.25 m

Kovats' RI, polar column, isothermal

View large format table.

Column type Active phase Temperature (C) I Reference Comment
CapillaryCarbowax 40M150.1497.2Rudenko and Rudenko, 2005He; Column diameter: 0.25 mm
CapillaryCarbowax 40M170.1516.9Rudenko and Rudenko, 2005He; Column diameter: 0.25 mm
CapillaryCarbowax 40M190.1549.3Rudenko and Rudenko, 2005He; Column diameter: 0.25 mm
CapillaryCarbowax 40M150.1497.2Rudenko and Rudenko, 2000He; Column diameter: 0.25 mm
CapillaryCarbowax 40M170.1516.9Rudenko and Rudenko, 2000He; Column diameter: 0.25 mm
CapillaryCarbowax 40M190.1549.3Rudenko and Rudenko, 2000He; Column diameter: 0.25 mm

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

View large format table.

Column type Active phase I Reference Comment
CapillaryDB-11316.Peng, 200015. m/0.53 mm/1. μm, He; Program: 40C(3min) => 8C/min => 200(1min) => 5C/min => 300C(25min)

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

View large format table.

Column type Active phase I Reference Comment
CapillaryDB-Wax1519.Bertoli, Menichini, et al., 200430. m/0.25 mm/0.25 μm, N2, 60. C @ 10. min, 5. K/min; Tend: 220. C
CapillaryDB-Wax1521.Peng, 200015. m/0.53 mm/1. μm, He, 40. C @ 3. min, 5. K/min, 220. C @ 30. min
CapillaryHP-Wax1510.Peng, 200015. m/0.53 mm/1. μm, He, 40. C @ 3. min, 5. K/min, 220. C @ 30. min

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

View large format table.

Column type Active phase I Reference Comment
CapillarySqualane1326.Chen, 2008Program: not specified
CapillaryMethyl Silicone1384.N/AProgram: not specified

References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, 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.

Smith and Easley, 1963
Smith, J.O.; Easley, K.W., Ortho-substituted bicyclohexyl hydrocarbons as high energy fuels, Patent No. 3,113,425 to Monsanto Research Corp., Everett, MA, USA 12/10/63, 1963, 1. [all data]

Gollis, Belenyessy, et al., 1962
Gollis, M.H.; Belenyessy, L.I.; Gudzinowicz, B.J.; Koch, S.D.; Smith, J.O.; Wineman, R.J., Evaluation of pure hydrocarbons as jet fuels, J. Chem. Eng. Data, 1962, 7, 331-316. [all data]

Coops, Van Kamp, et al., 1960
Coops, J.; Van Kamp, H.; Lambregts, W.A.; Visser, B.J.; Dekker, H., Thermal quantities of cycloparaffins. Part IV. Heats of combustion of cycloparaffins with 10-17 C atoms, Rec. Trav. Chim. Pays/Bas, 1960, 79, 1226-1234. [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]

Drotloff and Moller, 1987
Drotloff, H.; Moller, M., On the phase transitions of cycloalkanes, Thermochim. Acta, 1987, 112, 1, 57, https://doi.org/10.1016/0040-6031(87)88079-6 . [all data]

Mueller, Padeken, et al., 1965
Mueller, E.; Padeken, H.G.; Salamon, M.; Fiedler, G., Direct Photooxidation of Cycloalkanes, Chem. Ber., 1965, 98, 1893-1909. [all data]

Gollis, Belenyessy, et al., 1962, 2
Gollis, M.H.; Belenyessy, L.I.; Gudzinowicz, B.J.; Koch, S.D.; Smith, J.O.; Wineman, R.J., Evaluation of pure hydrocarbons as jet fuels., J. Chem. Eng. Data, 1962, 7, 311-6. [all data]

Chickos, Hesse, et al., 1998
Chickos, James; Hesse, Donald; Hosseini, Sarah; Nichols, Gary; Webb, Paul, Sublimation enthalpies at 298.15K using correlation gas chromatography and differential scanning calorimetry measurements, Thermochimica Acta, 1998, 313, 2, 101-110, https://doi.org/10.1016/S0040-6031(97)00432-2 . [all data]

Chickos, Hosseini, et al., 1995
Chickos, James S.; Hosseini, Sarah; Hesse, Donald G., Determination of vaporization enthalpies of simple organic molecules by correlations of changes in gas chromatographic net retention times, Thermochimica Acta, 1995, 249, 41-62, https://doi.org/10.1016/0040-6031(95)90670-3 . [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]

Meyer and Hotz, 1976
Meyer, Edwin F.; Hotz, Carol A., Cohesive energies in polar organic liquids. 3. Cyclic ketones, J. Chem. Eng. Data, 1976, 21, 3, 274-279, https://doi.org/10.1021/je60070a035 . [all data]

Drotloff and Möller, 1987
Drotloff, Hansotto; Möller, Martin, On the phase transitions of cycloalkanes, Thermochimica Acta, 1987, 112, 1, 57-62, https://doi.org/10.1016/0040-6031(87)88079-6 . [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]

Sicher, Svoboda, et al., 1968
Sicher, J.; Svoboda, M.; Mallon, B.J.; Turner, R.B., Stereochemical studies. Part XLVII. Conformational analysis of many-membered ring compounds. The cyclododecenes, J. Chem. Soc. B, 1968, 441-447. [all data]

Golubitskii, Kulikov, et al., 1979
Golubitskii, A.E.; Kulikov, N.S.; Zyakun, A.M.; Valovoi, V.A.; Alekseev, A.M.; Volkov, V.N., Photoionization mass spectra of alicyclic compounds with various substituents, and their ionization energies and appearance energies, Bull. Acad. Sci. USSR, Div. Chem. Sci., 1979, 11, 2602. [all data]

Puttemans, 1974
Puttemans, J.P., Ionisation de cycloalcanes (C5 a C12) en spectroscopie photoelectronique et par impact electronique, Ing. Chim. (Brussels), 1974, 56, 64. [all data]

Rudenko and Rudenko, 2005
Rudenko, B.A.; Rudenko, G.I., Gas chromatography with open tubular columns of cyclododecane derivatives, J. Anal. Chem. USSR (Engl. Transl.), 2005, 60, 4, 345-348. [all data]

Rudenko and Rudenko, 2000
Rudenko, B.A.; Rudenko, G.I., Capillary chromatography of cyclododecane derivatives, Proceedings, 23rd ISCC; CD-ROM, 2000, retrieved from http://www.richrom.com/assets/CD23PDF. [all data]

Boneva and Balbolov, 1993
Boneva, S.; Balbolov, E., Capillary gas chromatography of hydrogenation products of 1,5,9-cyclododecatriene stereoisomers, Chromatographia, 1993, 37, 5/6, 277-280, https://doi.org/10.1007/BF02278633 . [all data]

Engewald, Billing, et al., 1987
Engewald, W.; Billing, U.; Welsch, T.; Haufe, G., Structure-retention correlations of hydrocarbons in gas-liquid and gas-solid chromatography. Cycloalkenes and cycloalkadienes, Chromatographia, 1987, 23, 8, 590-594, https://doi.org/10.1007/BF02324870 . [all data]

Engewald, Epsch, et al., 1974
Engewald, W.; Epsch, K.; Graefe, J.; Welsch, Th., Molekülstruktur und retentionsverhalten. II. Retentionsverhalten cycloaliphatischer kohlenwasser-stoffe bei der gas-adsorptions- und gas-verteilungschromatographie, J. Chromatogr., 1974, 91, 623-631, https://doi.org/10.1016/S0021-9673(01)97943-9 . [all data]

Schomburg, 1967
Schomburg, G., Struktur und Retentionsverhalten von Offenkettigen und Cyclischen Kohlenwasserstoffen und Deren Einfacher Substitutionsprodukte, Anal. Chim. Acta., 1967, 38, 45-64, https://doi.org/10.1016/S0003-2670(01)80560-2 . [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]

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]

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]

Bertoli, Menichini, et al., 2004
Bertoli, A.; Menichini, F.; Noccioli, C.; Morelli, I.; Pistelli, L., Volatile constituents of different organs of Psoralea bituminosa L., Flavour Fragr. J., 2004, 19, 2, 166-171, https://doi.org/10.1002/ffj.1315 . [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]


Notes

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