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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Gas phase thermochemistry data
Go To: Top, Condensed phase thermochemistry data, Phase change data, Henry's Law data, Gas phase ion energetics data, Mass spectrum (electron ionization), References, Notes
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
GT - Glushko Thermocenter, Russian Academy of Sciences, Moscow
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°gas | 44.6 | kcal/mol | Chyd | Roth, Bohm, et al., 1983 | ALS |
Quantity | Value | Units | Method | Reference | Comment |
S°gas | 75.44 ± 0.25 | cal/mol*K | N/A | Finke H.L., 1956 | GT |
Constant pressure heat capacity of gas
Cp,gas (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
8.114 | 50. | Dorofeeva O.V., 1986 | Recommended S(298.15 K) value agrees with experimental value within its uncertainty. Value of S(298.15 K) calculated by [ Evans M.V., 1960] is 2.4 J/mol*K larger than experimental one.; GT |
10.10 | 100. | ||
13.27 | 150. | ||
16.98 | 200. | ||
23.18 | 273.15 | ||
25.39 ± 0.84 | 298.15 | ||
25.559 | 300. | ||
34.130 | 400. | ||
41.522 | 500. | ||
47.605 | 600. | ||
52.603 | 700. | ||
56.761 | 800. | ||
60.263 | 900. | ||
63.231 | 1000. | ||
65.765 | 1100. | ||
67.935 | 1200. | ||
69.802 | 1300. | ||
71.413 | 1400. | ||
72.808 | 1500. |
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 |
Henry's Law 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: Rolf Sander
Henry's Law constant (water solution)
kH(T) = k°H exp(d(ln(kH))/d(1/T) ((1/T) - 1/(298.15 K)))
k°H = Henry's law constant for solubility in water at 298.15 K (mol/(kg*bar))
d(ln(kH))/d(1/T) = Temperature dependence constant (K)
k°H (mol/(kg*bar)) | d(ln(kH))/d(1/T) (K) | Method | Reference | Comment |
---|---|---|---|---|
0.21 | Q | N/A | missing citation give several references for the Henry's law constants but don't assign them to specific species. |
Gas phase ion energetics 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:
B - John E. Bartmess
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron
View reactions leading to C7H8+ (ion structure unspecified)
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
8.29 | PI | Traeger and McLoughlin, 1978 | LLK |
8.03 | PE | Traeger and McLoughlin, 1978 | LLK |
8.52 | EI | Hoffman, 1974 | LLK |
8.40 | PE | Bodor, Dewar, et al., 1970 | RDSH |
8.20 ± 0.05 | PI | Akopyan and Vilesov, 1966 | RDSH |
8.28 | S | Price, Passmore, et al., 1963 | RDSH |
8.50 | PE | Muller, Schweig, et al., 1974 | Vertical value; LLK |
Appearance energy determinations
Ion | AE (eV) | Other Products | Method | Reference | Comment |
---|---|---|---|---|---|
C5H5+ | 16.66 | ? | EI | Harrison, Haynes, et al., 1965 | RDSH |
C5H5+ | 16.0 | ? | EI | Lifshitz and Bauer, 1963 | RDSH |
C6H5+ | 14.17 | CH3 | EI | Hoffman, 1974 | LLK |
C7H7+ | 9.36 | H | PI | Traeger and McLoughlin, 1978 | LLK |
C7H7+ | 9.36 ± 0.02 | H | TE | Traeger and McLoughlin, 1977 | LLK |
C7H7+ | 10.73 | H | EI | Hoffman, 1974 | LLK |
C7H7+ | ≤10.0 | H | PI | Akopyan and Vilesov, 1966 | RDSH |
C7H7+ | 10.1 ± 0.2 | H | EI | Harrison, Honnen, et al., 1960 | RDSH |
De-protonation reactions
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 |
Mass spectrum (electron ionization)
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Henry's Law data, Gas phase ion energetics data, References, Notes
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 | Japan AIST/NIMC Database- Spectrum MS-NW- 968 |
NIST MS number | 230230 |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Henry's Law data, Gas phase ion energetics data, Mass spectrum (electron ionization), Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Roth, Bohm, et al., 1983
Roth, W.R.; Bohm, M.; Lenhartz, H-W.; Vogel, E.,
Heats of hydrogenation. Part 5. Resonance energy of bridged [10]annulenes,
Angew. Chem., 1983, 95, 1011-1012. [all data]
Finke H.L., 1956
Finke H.L.,
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]
Dorofeeva O.V., 1986
Dorofeeva O.V.,
Thermodynamic properties of twenty-one monocyclic hydrocarbons,
J. Phys. Chem. Ref. Data, 1986, 15, 437-464. [all data]
Evans M.V., 1960
Evans M.V.,
Vibrational spectra and structure of the tropilidene molecule,
J. Am. Chem. Soc., 1960, 82, 1876-1882. [all data]
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]
Traeger and McLoughlin, 1978
Traeger, J.C.; McLoughlin, R.G.,
A photoionization study of the energetics of C7H7+ ion formed from C7H8 precursors,
Int. J. Mass Spectrom. Ion Phys., 1978, 27, 319. [all data]
Hoffman, 1974
Hoffman, M.K.,
Hidden rearrangements in the mass spectral decomposition of cycloheptatriene,
Z. Naturforsch. A:, 1974, 29, 1077. [all data]
Bodor, Dewar, et al., 1970
Bodor, N.; Dewar, M.J.S.; Worley, S.D.,
Photoelectron spectra of molecules. III. Ionization potentials of some cyclic hydrocarbons and their derivatives, and heats of formation and ionization potentials calculated by the MINDO SCF MO method,
J. Am. Chem. Soc., 1970, 92, 19. [all data]
Akopyan and Vilesov, 1966
Akopyan, M.E.; Vilesov, F.I.,
A mass-spectrometric study of the photo-ionisation of benzene derivatives at wavelengths up to 885 A,
Zh. Fiz. Khim., 1966, 40, 125, In original 63. [all data]
Price, Passmore, et al., 1963
Price, W.C.; Passmore, T.R.; Roessler, D.M.,
[Title unavailable],
Faraday Discuss. Chem. Soc., 1963, 35, 238. [all data]
Muller, Schweig, et al., 1974
Muller, C.; Schweig, A.; Vermeer, H.,
Methode zur Berechnung induktiver und konjugativer Effekte - Andwendung auf Tropon,
Angew. Chem., 1974, 86, 275. [all data]
Harrison, Haynes, et al., 1965
Harrison, A.G.; Haynes, P.; McLean, S.; Meyer, F.,
The mass spectra of methyl-substituted cyclopentadienes,
J. Am. Chem. Soc., 1965, 87, 5099. [all data]
Lifshitz and Bauer, 1963
Lifshitz, C.; Bauer, S.H.,
Mass spectra of valence tautomers,
J. Phys. Chem., 1963, 67, 1629. [all data]
Traeger and McLoughlin, 1977
Traeger, J.C.; McLoughlin, R.G.,
Threshold photoionization and dissociation of toluene and cycloheptatriene,
J. Am. Chem. Soc., 1977, 99, 7351. [all data]
Harrison, Honnen, et al., 1960
Harrison, A.G.; Honnen, L.R.; Dauben, H.J., Jr.; Lossing, F.P.,
Free radicals by mass spectrometry. XX. Ionization potentials of cyclopentadienyl and cycloheptatrienyl radicals,
J. Am. Chem. Soc., 1960, 82, 5593. [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]
Notes
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Henry's Law data, Gas phase ion energetics data, Mass spectrum (electron ionization), References
- Symbols used in this document:
AE Appearance energy Cp,gas Constant pressure heat capacity of gas Cp,liquid Constant pressure heat capacity of liquid S°gas Entropy of gas at standard conditions S°liquid Entropy of liquid at standard conditions Tboil Boiling point Ttriple Triple point temperature d(ln(kH))/d(1/T) Temperature dependence parameter for Henry's Law constant k°H Henry's Law constant at 298.15K ΔHtrs Enthalpy of phase transition ΔStrs Entropy of phase transition ΔcH°liquid Enthalpy of combustion of liquid at standard conditions ΔfH°gas Enthalpy of formation of gas 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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