Cyclotetradecane

• Formula: C₁₄H₂₈
• Molecular weight: 196.3721
• IUPAC Standard InChI: InChI=1S/C14H28/c1-2-4-6-8-10-12-14-13-11-9-7-5-3-1/h1-14H2 Copy

  
• IUPAC Standard InChIKey: KATXJJSCAPBIOB-UHFFFAOYSA-N Copy
• CAS Registry Number: 295-17-0
• Chemical structure:
  This structure is also available as a 2d Mol file or as a computed 3d SD file
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• Information on this page:
  • Gas phase thermochemistry data
  • Phase change data
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • Gas Chromatography
  • References
  • Notes
• Other data available:
  • Condensed phase thermochemistry data
  • Reaction thermochemistry 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 by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

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
DRB - Donald R. Burgess, Jr.
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Enthalpy of vaporization

Enthalpy of sublimation

Enthalpy of fusion

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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Additional Data

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

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, temperature ramp

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References

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

Frisch, Bautista, et al., 1964
Frisch, M.A.; Bautista, R.G.; Margrave, J.L.; Parsons, C.G.; Wotiz, J.H., Strain energies in hydrocarbons from heats of combustion. II. Concerning the possibility of a transannular interaction in 1,8-cyclotetradecadiyne, J. Am. Chem. Soc., 1964, 86, 335-336. [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]

Frisch, 1962
Frisch, M.A., A high precision calorimeter for ther measurement of small energy differences, Ph.D. Thesis for University of Wisconsin, 1962, 1-100. [all data]

Chickos, Hesse, et al., 1990
Chickos, J.S.; Hesse, D.G.; Liebman, J.F., Estimating entropies and enthalpies of fusion of hydrocarbons, J. Org. Chem., 1990, 55, 3833-40. [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]

Sondheimer, Amiel, et al., 1957
Sondheimer, F.; Amiel, Y.; Wolovsky, R., Unsaturated Macrocyclic Compounds IV. The Oxidation of Terminal Diacetylenes to Macrocyclic Tetraacetaylenes, J. Am. Chem. Soc., 1957, 79, 6263. [all data]

Chickos, Hesse, et al., 1992
Chickos, James S.; Hesse, Donald G.; Panshin, Sandra Y.; Rogers, Donald W.; Saunders, Martin; Uffer, Philip M.; Liebman, Joel F., The strain energy of cyclotetradecane is small, J. Org. Chem., 1992, 57, 6, 1897-1899, https://doi.org/10.1021/jo00032a052 . [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]

Cox and Pilcher, 1970, 2
Cox, J.D.; Pilcher, G., Thermochemistry of Organic and Organometallic Compounds, Academic Press Inc., London, 1970, 643. [all data]

Engelsman, 1955
Engelsman, J.J., , Ph.D. Thesis, Vrije Universiteit Te Amsterdam, 1955. [all data]

Borgen and Dale, 1970
Borgen, Gerd; Dale, Johannes, Conformational analysis of 14- and 16-membered rings, J. Chem. Soc. D, 1970, 20, 1340b, https://doi.org/10.1039/c2970001340b . [all data]

Liu J.M., Nan P., et al., 2006
Liu J.M.; Nan P.; Tsering Q.; Tsering T.; Bai Z.K.; Wang L.; Liu Z.J.; Zhong Y., Volatile constituents of the leaves and flowers of Salvia przewalskii Maxim. from Tibet, Flavour Fragr. J., 2006, 21, 3, 435-438, https://doi.org/10.1002/ffj.1607 . [all data]

Bruni, Pellati, et al., 2005
Bruni, R.; Pellati, F.; Grazia Bellardi, M.; Benvenuti, S.; Paltrinieri, S.; Bertaccini, A.; Bianchi, A., Herbal drug quality and phytochemical composition of Hypericum perforatum L. affected by ash yellows phytoplasma infection, J. Agric. Food Chem., 2005, 53, 4, 964-968, https://doi.org/10.1021/jf0487654 . [all data]

Robledo and Arzuffi, 2004
Robledo, N.; Arzuffi, R., Identificacion de los compuestos volatiles de papaya y cuaguayote mediante microextraccion en fase solida, cromatografia de gases y espectrometria de masas, Rev. Latinoamericana Quim., 2004, 32, 1, 30-36. [all data]

Notes

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• Symbols used in this document:
  

  Tfus	Fusion (melting) point
  ΔfH°gas	Enthalpy of formation of gas at standard conditions
  ΔfusH	Enthalpy of fusion
  ΔsubH	Enthalpy of sublimation
  ΔsubH°	Enthalpy of sublimation 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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