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
- IUPAC Standard InChIKey: KATXJJSCAPBIOB-UHFFFAOYSA-N
- 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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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 |
|---|---|---|---|---|---|
| ΔfH°gas | -57.18 ± 0.56 | kcal/mol | Ccb | Frisch, Bautista, et al., 1964 | Reanalyzed 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 |
|---|---|---|---|---|---|
| ΔfH°solid | -88.94 ± 0.98 | kcal/mol | Ccb | Frisch, Bautista, et al., 1964 | see Frisch, 1962 |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔcH°solid | -2184.19 ± 0.88 | kcal/mol | Ccb | Frisch, Bautista, et al., 1964 | see Frisch, 1962; Corresponding ΔfHºsolid = -88.94 kcal/mol (simple calculation by NIST; no Washburn corrections) |
| ΔcH°solid | -2183.68 ± 0.31 | kcal/mol | Ccb | Coops, Van Kamp, et al., 1960 | Reanalyzed by Cox and Pilcher, 1970, Original value = -2183.5 ± 0.31 kcal/mol; Corresponding ΔfHºsolid = -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 |
|---|---|---|---|---|---|
| Tfus | 330. | K | N/A | Chickos, Hesse, et al., 1990 | Crystal phase 1 phase; Uncertainty assigned by TRC = 1. K; TRC |
| Tfus | 329. | K | N/A | Drotloff and Moller, 1987 | Crystal phase 1 phase; Uncertainty assigned by TRC = 0.3 K; TRC |
| Tfus | 325. | K | N/A | Sondheimer, Amiel, et al., 1957 | Uncertainty assigned by TRC = 3. K; TRC |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔvapH° | 15.6 ± 0.05 | kcal/mol | N/A | Chickos, Hesse, et al., 1992 | AC |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔsubH° | 22.8 | kcal/mol | CGC-DSC | Chickos, Hesse, et al., 1998 | AC |
| ΔsubH° | 31.76 | kcal/mol | N/A | Frisch, Bautista, et al., 1964 | DRB |
Enthalpy of vaporization
| ΔvapH (kcal/mol) | Temperature (K) | Reference | Comment |
|---|---|---|---|
| 14.9 ± 0.05 | 343. | Chickos, Hesse, et al., 1992 | AC |
Enthalpy of sublimation
| ΔsubH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
|---|---|---|---|---|
| 23.4 ± 0.41 | 310. | HSA | Chickos, Hesse, et al., 1992 | Based on data from 300. to 321. K.; AC |
| 32.21 ± 0.35 | 355. | V | Frisch, Bautista, et al., 1964 | see Frisch, 1962; ALS |
| 32.22 ± 0.36 | 301. | ME | Frisch, Bautista, et al., 1964 | Based on data from 295. to 307. K. See also Cox and Pilcher, 1970, 2.; AC |
| 21.3 ± 0.1 | 287. | TM | Engelsman, 1955 | Based on data from 285. to 290. K.; AC |
Enthalpy of fusion
| ΔfusH (kcal/mol) | Temperature (K) | Reference | Comment |
|---|---|---|---|
| 6.86 | 328. | Borgen and Dale, 1970 | AC |
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
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -125.4 ± 0.14 | kcal/mol | Chyd | Turner, Jarrett, et al., 1973 | liquid phase; solvent: Acetic acid |
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
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | HP-5 | 1673. | Liu J.M., Nan P., et al., 2006 | 30. m/0.25 mm/0.25 μm, He, 60. C @ 2. min, 10. K/min, 250. C @ 10. min |
Van Den Dool and Kratz RI, non-polar column, custom temperature program
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | SE-52 | 1677. | Bruni, Pellati, et al., 2005 | 30. m/0.32 mm/0.15 μm, He; Program: 45C => 1C/min => 100C => 5C/min => 250C(10min) |
Normal alkane RI, non-polar column, temperature ramp
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | DB-5MS | 1669. | Robledo and Arzuffi, 2004 | 30. m/0.25 mm/0.25 μm, 30. K/min, 200. C @ 10. min; Tstart: 90. C |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, 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]
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]
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
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas Chromatography, References
- Symbols used in this document:
Tfus Fusion (melting) point ΔcH°solid Enthalpy of combustion of solid at standard conditions ΔfH°gas Enthalpy of formation of gas at standard conditions ΔfH°solid Enthalpy of formation of solid at standard conditions 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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