Cyclotetradecane

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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
Δfgas-57.18 ± 0.56kcal/molCcbFrisch, Bautista, et al., 1964Reanalyzed by Cox and Pilcher, 1970, Original value = -56.73 ± 0.76 kcal/mol; see Frisch, 1962

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
Δfsolid-88.94 ± 0.98kcal/molCcbFrisch, Bautista, et al., 1964see Frisch, 1962
Quantity Value Units Method Reference Comment
Δcsolid-2184.19 ± 0.88kcal/molCcbFrisch, Bautista, et al., 1964see Frisch, 1962; Corresponding Δfsolid = -88.94 kcal/mol (simple calculation by NIST; no Washburn corrections)
Δcsolid-2183.68 ± 0.31kcal/molCcbCoops, Van Kamp, et al., 1960Reanalyzed by Cox and Pilcher, 1970, Original value = -2183.5 ± 0.31 kcal/mol; Corresponding Δfsolid = -89.450 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
DRB - Donald R. Burgess, Jr.
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Quantity Value Units Method Reference Comment
Tfus330.KN/AChickos, Hesse, et al., 1990Crystal phase 1 phase; Uncertainty assigned by TRC = 1. K; TRC
Tfus329.KN/ADrotloff and Moller, 1987Crystal phase 1 phase; Uncertainty assigned by TRC = 0.3 K; TRC
Tfus325.KN/ASondheimer, Amiel, et al., 1957Uncertainty assigned by TRC = 3. K; TRC
Quantity Value Units Method Reference Comment
Δvap15.6 ± 0.05kcal/molN/AChickos, Hesse, et al., 1992AC
Quantity Value Units Method Reference Comment
Δsub22.8kcal/molCGC-DSCChickos, Hesse, et al., 1998AC
Δsub31.76kcal/molN/AFrisch, Bautista, et al., 1964DRB

Enthalpy of vaporization

ΔvapH (kcal/mol) Temperature (K) Reference Comment
14.9 ± 0.05343.Chickos, Hesse, et al., 1992AC

Enthalpy of sublimation

ΔsubH (kcal/mol) Temperature (K) Method Reference Comment
23.4 ± 0.41310.HSAChickos, Hesse, et al., 1992Based on data from 300. to 321. K.; AC
32.21 ± 0.35355.VFrisch, Bautista, et al., 1964see Frisch, 1962; ALS
32.22 ± 0.36301.MEFrisch, Bautista, et al., 1964Based on data from 295. to 307. K. See also Cox and Pilcher, 1970, 2.; AC
21.3 ± 0.1287.TMEngelsman, 1955Based on data from 285. to 290. K.; AC

Enthalpy of fusion

ΔfusH (kcal/mol) Temperature (K) Reference Comment
6.86328.Borgen and Dale, 1970AC

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

4Hydrogen + 1,8-Cyclotetradecadiyne = Cyclotetradecane

By formula: 4H2 + C14H20 = C14H28

Quantity Value Units Method Reference Comment
Δr-125.4 ± 0.14kcal/molChydTurner, Jarrett, et al., 1973liquid phase; solvent: Acetic acid

References

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

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]

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]

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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