1,8-Cyclotetradecadiyne
- Formula: C14H20
- Molecular weight: 188.3086
- IUPAC Standard InChIKey: BVTCHBNCNJEJTD-UHFFFAOYSA-N
- CAS Registry Number: 1540-80-3
- Chemical structure:
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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 | 313.8 ± 4.0 | kJ/mol | Ccb | Frisch, Bautista, et al., 1964 | 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 | 147.7 ± 2.3 | kJ/mol | Ccb | Frisch, Bautista, et al., 1964 | see Frisch, 1962 |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°solid | -8515.2 ± 1.7 | kJ/mol | Ccb | Frisch, Bautista, et al., 1964 | see Frisch, 1962; Corresponding ΔfHºsolid = 147.7 kJ/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 | 370. | K | N/A | Chickos, Hesse, et al., 1990 | Uncertainty assigned by TRC = 0.3 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔsubH° | 94.3 | kJ/mol | CGC-DSC | Chickos, Hesse, et al., 1998 | AC |
ΔsubH° | 166.1 | kJ/mol | N/A | Frisch, Bautista, et al., 1964 | DRB |
Antoine Equation Parameters
log10(P) = A − (B / (T + C))
P = vapor pressure (bar)
T = temperature (K)
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Temperature (K) | A | B | C | Reference | Comment |
---|---|---|---|---|---|
317.09 to 332.39 | 3.85915 | 686.983 | -233.124 | Frisch, Bautista, et al., 1964 | Coefficents calculated by NIST from author's data. |
Enthalpy of sublimation
ΔsubH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
87.6 ± 1.0 | 338. | HSA | Chickos, Hesse, et al., 1998 | Based on data from 315. to 364. K.; AC |
166.0 ± 3.2 | 355. | V | Frisch, Bautista, et al., 1964 | see Frisch, 1962; ALS |
166.0 ± 3.2 | 325. | ME | Frisch, Bautista, et al., 1964 | Based on data from 317. to 332. K. See also Cox and Pilcher, 1970.; AC |
Enthalpy of fusion
ΔfusH (kJ/mol) | Temperature (K) | Reference | Comment |
---|---|---|---|
22.6 | 370. | Augdahl, Borgen, et al., 1974 | 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
By formula: 4H2 + C14H20 = C14H28
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -524.7 ± 0.59 | kJ/mol | Chyd | Turner, Jarrett, et al., 1973 | liquid phase; solvent: Acetic acid |
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
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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 | Chemical Concepts |
NIST MS number | 155380 |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Mass spectrum (electron ionization), NIST Subscription Links, 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]
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]
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
Cox, J.D.; Pilcher, G.,
Thermochemistry of Organic and Organometallic Compounds, Academic Press Inc., London, 1970, 643. [all data]
Augdahl, Borgen, et al., 1974
Augdahl, Else; Borgen, Gerd; Dale, Johannes; Krane, Jostein; Taticchi, A.; Mannervik, Bengt,
The Conformations of Cyclotetradeca-1,8-diyne.,
Acta Chem. Scand., 1974, 28b, 125-129, https://doi.org/10.3891/acta.chem.scand.28b-0125
. [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 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 - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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