1,3,5-Cycloheptatriene
- Formula: C7H8
- Molecular weight: 92.1384
- IUPAC Standard InChIKey: CHVJITGCYZJHLR-UHFFFAOYSA-N
- CAS Registry Number: 544-25-2
- Chemical structure:
This structure is also available as a 2d Mol file or as a computed 3d SD file
The 3d structure may be viewed using Java or Javascript. - Other names: Tropilidene; Cyclohepta-1,3,5-triene; Cycloheptatriene; Tropilidin; UN 2603
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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 as indicated in comments:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DH - Eugene S. Domalski and Elizabeth D. Hearing
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔcH°liquid | -965.6 ± 0.5 | kcal/mol | Ccb | Jackson, Hung, et al., 1971 | Corresponding ΔfHºliquid = 34.0 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS |
Quantity | Value | Units | Method | Reference | Comment |
S°liquid | 51.300 | cal/mol*K | N/A | Finke, Scott, et al., 1956 | DH |
Constant pressure heat capacity of liquid
Cp,liquid (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
38.901 | 298.15 | Finke, Scott, et al., 1956 | T = 10 to 320 K.; DH |
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:
BS - Robert L. Brown and Stephen E. Stein
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
AC - William E. Acree, Jr., James S. Chickos
CAL - James S. Chickos, William E. Acree, Jr., Joel F. Liebman, Students of Chem 202 (Introduction to the Literature of Chemistry), University of Missouri -- St. Louis
DH - Eugene S. Domalski and Elizabeth D. Hearing
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tboil | 389.7 | K | N/A | Aldrich Chemical Company Inc., 1990 | BS |
Quantity | Value | Units | Method | Reference | Comment |
Ttriple | 197.92 | K | N/A | McCullough and Waddington, 1957 | Uncertainty assigned by TRC = 0.07 K; IPTS-48; TRC |
Ttriple | 197.91 | K | N/A | Finke, Scott, et al., 1956, 2 | Crystal phase 1 phase; Uncertainty assigned by TRC = 0.07 K; TRC |
Ttriple | 197.92 | K | N/A | Finke, Scott, et al., 1956, 2 | Crystal phase 1 phase; Uncertainty assigned by TRC = 0.05 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 9.250 ± 0.050 | kcal/mol | V | Finke, Scott, et al., 1956, 3 | ALS |
ΔvapH° | 9.25 ± 0.05 | kcal/mol | N/A | Finke, Scott, et al., 1956 | AC |
Reduced pressure boiling point
Tboil (K) | Pressure (atm) | Reference | Comment |
---|---|---|---|
390.2 | 0.986 | Weast and Grasselli, 1989 | BS |
333.7 | 0.161 | Weast and Grasselli, 1989 | BS |
Enthalpy of vaporization
ΔvapH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
9.75 | 288. | A | Stephenson and Malanowski, 1987 | Based on data from 273. to 338. K. See also Kkykj and Repas, 1973.; AC |
9.42 | 288. | A,EB | Stephenson and Malanowski, 1987 | Based on data from 273. to 416. K. See also Finke, Scott, et al., 1956.; AC |
Antoine Equation Parameters
log10(P) = A − (B / (T + C))
P = vapor pressure (atm)
T = temperature (K)
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Temperature (K) | A | B | C | Reference | Comment |
---|---|---|---|---|---|
273. to 338. | 4.17940 | 1422.104 | -48.151 | Finke, Scott, et al., 1956 | Coefficents calculated by NIST from author's data. |
Enthalpy of fusion
ΔfusH (kcal/mol) | Temperature (K) | Reference | Comment |
---|---|---|---|
0.277 | 198. | Domalski and Hearing, 1996 | AC |
Entropy of fusion
ΔfusS (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
3.642 | 154.0 | Domalski and Hearing, 1996 | CAL |
1.40 | 198.0 |
Enthalpy of phase transition
ΔHtrs (kcal/mol) | Temperature (K) | Initial Phase | Final Phase | Reference | Comment |
---|---|---|---|---|---|
0.56090 | 153.98 | crystaline, II | crystaline, I | Finke, Scott, et al., 1956 | DH |
0.27739 | 197.92 | crystaline, I | liquid | Finke, Scott, et al., 1956 | DH |
Entropy of phase transition
ΔStrs (cal/mol*K) | Temperature (K) | Initial Phase | Final Phase | Reference | Comment |
---|---|---|---|---|---|
3.642 | 153.98 | crystaline, II | crystaline, I | Finke, Scott, et al., 1956 | DH |
1.40 | 197.92 | crystaline, I | liquid | Finke, Scott, et al., 1956 | DH |
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 as indicated in comments:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
B - John E. Bartmess
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: 3H2 + C7H8 = C7H14
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -72.8 ± 0.1 | kcal/mol | Chyd | Roth, Klaerner, et al., 1983 | liquid phase; solvent: Isooctane; ALS |
ΔrH° | -70.49 ± 0.39 | kcal/mol | Chyd | Turner, Meador, et al., 1957 | liquid phase; solvent: Acetic acid; ALS |
ΔrH° | -72.11 ± 0.30 | kcal/mol | Chyd | Conn, Kistiakowsky, et al., 1939 | gas phase; Reanalyzed by Cox and Pilcher, 1970, Original value = -72.85 ± 0.01 kcal/mol; at 355 K; ALS |
C7H7- + =
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 375.2 ± 2.2 | kcal/mol | G+TS | Bartmess, Scott, et al., 1979 | gas phase; value altered from reference due to change in acidity scale; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 369.2 ± 2.0 | kcal/mol | IMRE | Bartmess, Scott, et al., 1979 | gas phase; value altered from reference due to change in acidity scale; B |
By formula: C7H8 = C7H8
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 0.160 | kcal/mol | Eqk | Gorlitz and Gunther, 1969 | liquid phase; NMR; ALS |
References
Go To: Top, 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.
Jackson, Hung, et al., 1971
Jackson, W.; Hung, T.S.; Hopkins, H.P., Jr.,
Delocalization energies of troponoids from bomb calorimetric and vapour pressure measurements,
J. Chem. Thermodyn., 1971, 3, 347-353. [all data]
Finke, Scott, et al., 1956
Finke, H.L.; Scott, D.W.; Gross, M.E.; Messerly, J.F.; Waddington, G.,
Cycloheptane, cyclooctane and 1,3,5-cycloheptatriene. Low temperature thermal properties, vapor pressure and derived chemical thermodynamic properties,
J. Am. Chem. Soc., 1956, 78, 5469-5476. [all data]
Aldrich Chemical Company Inc., 1990
Aldrich Chemical Company Inc.,
Catalog Handbook of Fine Chemicals, Aldrich Chemical Company, Inc., Milwaukee WI, 1990, 1. [all data]
McCullough and Waddington, 1957
McCullough, J.P.; Waddington, G.,
Melting-point purity determinations: limitations as evidenced by calorimetric studies in the melting region,
Anal. Chim. Acta, 1957, 17, 80. [all data]
Finke, Scott, et al., 1956, 2
Finke, H.L.; Scott, D.W.; Gross, M.E.; Messerly, J.F.; Waddington, G.,
Cycloheptane, Cyclooctane and 1,3,5-Cycloheptatriene. Low Temperature Thermal Properties, Vapor Pressure and Derived Chemical Thermodynamic Prop.,
J. Am. Chem. Soc., 1956, 78, 5469. [all data]
Finke, Scott, et al., 1956, 3
Finke, H.L.; Scott, D.W.; Gross, M.E.; Messerly, J.F.; Waddington, G.,
Cycloheptane, cyclooctane and 1,3,5-cycloheptatriene. Low temperature thermal properties, vapor pressure and derived chemical thermodynamic properties,
J. Am. Chem. Soc., 1956, 78, 5469-54. [all data]
Weast and Grasselli, 1989
CRC Handbook of Data on Organic Compounds, 2nd Editon, Weast,R.C and Grasselli, J.G., ed(s)., CRC Press, Inc., Boca Raton, FL, 1989, 1. [all data]
Stephenson and Malanowski, 1987
Stephenson, Richard M.; Malanowski, Stanislaw,
Handbook of the Thermodynamics of Organic Compounds, 1987, https://doi.org/10.1007/978-94-009-3173-2
. [all data]
Kkykj and Repas, 1973
Kkykj, J.; Repas, M.,
Petrochemia, 1973, 13, 179. [all data]
Domalski and Hearing, 1996
Domalski, Eugene S.; Hearing, Elizabeth D.,
Heat Capacities and Entropies of Organic Compounds in the Condensed Phase. Volume III,
J. Phys. Chem. Ref. Data, 1996, 25, 1, 1, https://doi.org/10.1063/1.555985
. [all data]
Roth, Klaerner, et al., 1983
Roth, W.R.; Klaerner, F.G.; Gerit, F.; Grimme, W.; Koeser, H.G.; Busch, R.; Muskulus, B.; Breuckmann, R.; Scholz, B.P.; Lennartz, H.W.,
Stereochemistry of the bicyclo[2.1.0]pentane ring opening: thermolysis of tricyclo[3.2.0.0(,)]heptane derivatives,
Chem. Ber., 1983, 116, 2717-2737. [all data]
Turner, Meador, et al., 1957
Turner, R.B.; Meador, W.R.; Winkler, R.E.,
Heats of hydrogenation. I. Apparatus and the heats of hydrogenation of bicyclo[2,2,1]heptene, bicyclo[2,2,1]heptadiene, bicyclo[2,2,2]octene and bicyclo[2,2,2]octadiene,
J. Am. Chem. Soc., 1957, 79, 4116-4121. [all data]
Conn, Kistiakowsky, et al., 1939
Conn, J.B.; Kistiakowsky, G.B.; Smith, E.A.,
Heats of organic reactions. VIII. Some further hydrogenations, including those of some acetylenes,
J. Am. Chem. Soc., 1939, 61, 1868-1876. [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]
Bartmess, Scott, et al., 1979
Bartmess, J.E.; Scott, J.A.; McIver, R.T., Jr.,
The gas phase acidity scale from methanol to phenol,
J. Am. Chem. Soc., 1979, 101, 6047. [all data]
Gorlitz and Gunther, 1969
Gorlitz, M.; Gunther, H.,
Protonenresonanz-spektroskopie ungesattigter ringsysteme-XIII,
Tetrahedron, 1969, 25, 4467-4480. [all data]
Notes
Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, References
- Symbols used in this document:
Cp,liquid Constant pressure heat capacity of liquid S°liquid Entropy of liquid at standard conditions Tboil Boiling point Ttriple Triple point temperature ΔHtrs Enthalpy of phase transition ΔStrs Entropy of phase transition ΔcH°liquid Enthalpy of combustion of liquid at standard conditions ΔfusH Enthalpy of fusion ΔfusS Entropy of fusion ΔrG° Free energy of reaction at standard conditions ΔrH° Enthalpy of reaction 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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