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:
  • Phase change data
  • Reaction thermochemistry data
  • References
  • Notes
• Other data available:
  • Gas phase thermochemistry data
  • Condensed phase thermochemistry data
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • Gas Chromatography
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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

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

4 +  =

By formula: 4H₂ + C₁₄H₂₀ = C₁₄H₂₈

References

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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

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]

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]

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]

Cox and Pilcher, 1970
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]

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]

Notes

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• Symbols used in this document:
  

  Tfus	Fusion (melting) point
  ΔfusH	Enthalpy of fusion
  ΔrH°	Enthalpy of reaction at standard conditions
  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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