1,3-Cyclohexadiene
- Formula: C6H8
- Molecular weight: 80.1277
- IUPAC Standard InChIKey: MGNZXYYWBUKAII-UHFFFAOYSA-N
- CAS Registry Number: 592-57-4
- 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: Cyclohexa-1,3-diene; 1,2-Dihydrobenzene
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Condensed phase thermochemistry data
Go To: Top, Phase change 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
DH - Eugene S. Domalski and Elizabeth D. Hearing
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°liquid | 17.07 ± 0.15 | kcal/mol | Ccr | Steele, Chirico, et al., 1989 | ALS |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°liquid | -854.63 ± 0.13 | kcal/mol | Ccr | Steele, Chirico, et al., 1989 | Corresponding ΔfHºliquid = 17.07 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS |
Quantity | Value | Units | Method | Reference | Comment |
S°liquid | 47.151 | cal/mol*K | N/A | Geipel and Wolf, 1976 | DH |
Constant pressure heat capacity of liquid
Cp,liquid (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
33.77 | 298.15 | Steele, Chirico, et al., 1989 | DH |
34.551 | 298.15 | Geipel and Wolf, 1976 | T = 10 to 300 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
DRB - Donald R. Burgess, Jr.
AC - William E. Acree, Jr., James S. Chickos
DH - Eugene S. Domalski and Elizabeth D. Hearing
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tboil | 354. ± 2. | K | AVG | N/A | Average of 7 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 184. | K | N/A | White and Bishop, 1940 | Crystal phase 1 phase; Uncertainty assigned by TRC = 4. K; TRC |
Tfus | 168.4 | K | N/A | Kistiakowsky, Ruhoff, et al., 1936 | Uncertainty assigned by TRC = 0.3 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Ttriple | 161.0 | K | N/A | Geipel and Wolf, 1976, 2 | Uncertainty assigned by TRC = 0.2 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 7.93 ± 0.01 | kcal/mol | V | Steele, Chirico, et al., 1989 | ALS |
ΔvapH° | 7.93 | kcal/mol | N/A | Steele, Chirico, et al., 1989 | DRB |
ΔvapH° | 7.9 | kcal/mol | V | Rogers, 1972 | ALS |
Enthalpy of vaporization
ΔvapH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
7.79 | 322. | A,EB | Stephenson and Malanowski, 1987 | Based on data from 307. to 364. K. See also Meyer and Hotz, 1973.; AC |
7.74 | 308. | MM | Letcher and Marsicano, 1974 | Based on data from 304. to 322. K.; 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 |
---|---|---|---|---|
307.33 to 363.31 | 3.98464 ± 0.00048 | 1206.00 ± 0.87 | -50.83 ± 0.10 | Meyer and Hotz, 1973 |
Enthalpy of fusion
ΔfusH (kcal/mol) | Temperature (K) | Reference | Comment |
---|---|---|---|
1.0049 | 161.0 | Geipel and Wolf, 1976 | DH |
1.0 | 161. | Domalski and Hearing, 1996 | AC |
Entropy of fusion
ΔfusS (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
6.240 | 161.0 | Geipel and Wolf, 1976 | DH |
Gas phase ion energetics data
Go To: Top, Condensed phase thermochemistry data, Phase change 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 evaluated as indicated in comments:
HL - Edward P. Hunter and Sharon G. Lias
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
LBLHLM - Sharon G. Lias, John E. Bartmess, Joel F. Liebman, John L. Holmes, Rhoda D. Levin, and W. Gary Mallard
View reactions leading to C6H8+ (ion structure unspecified)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Proton affinity (review) | 200. | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
Quantity | Value | Units | Method | Reference | Comment |
Gas basicity | 192.3 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
8.25 | PE | Kimura, Katsumata, et al., 1981 | LLK |
8.25 ± 0.02 | PE | Bieri, Burger, et al., 1977 | LLK |
8.25 ± 0.03 | PI | Demeo and El-Sayed, 1970 | RDSH |
8.25 | PE | Bischof and Heilbronner, 1970 | RDSH |
8.28 ± 0.05 | EI | Franklin and Carroll, 1969 | RDSH |
8.32 | PE | Worley, Webb, et al., 1979 | Vertical value; LLK |
8.25 ± 0.03 | PE | Heilbronner, Hoshi, et al., 1976 | Vertical value; LLK |
Appearance energy determinations
Ion | AE (eV) | Other Products | Method | Reference | Comment |
---|---|---|---|---|---|
C3H2+ | 23.51 ± 0.50 | ? | EI | Franklin and Carroll, 1969 | RDSH |
C3H3+ | 14.87 ± 0.10 | ? | EI | Franklin and Carroll, 1969 | RDSH |
C3H4+ | 14.52 ± 0.10 | ? | EI | Franklin and Carroll, 1969 | RDSH |
C4H2+ | 19.81 ± 0.10 | C2H2+2H2 | EI | Franklin and Carroll, 1969 | RDSH |
C4H3+ | 17.62 ± 0.10 | C2H2+H2+H? | EI | Franklin and Carroll, 1969 | RDSH |
C4H4+ | 13.91 ± 0.20 | C2H2+H2 | EI | Franklin and Carroll, 1969 | RDSH |
C4H5+ | 14.69 ± 0.10 | C2H2+H | EI | Franklin and Carroll, 1969 | RDSH |
C4H6+ | 12.60 ± 0.10 | C2H2 | EI | Franklin and Carroll, 1969 | RDSH |
C5H3+ | 15.44 ± 0.10 | CH3+H2? | EI | Franklin and Carroll, 1969 | RDSH |
C5H5+ | 13.02 ± 0.10 | CH3 | EI | Franklin and Carroll, 1969 | RDSH |
C6H5+ | 13.92 ± 0.10 | H2+H | EI | Franklin and Carroll, 1969 | RDSH |
C6H6+ | 10.12 ± 0.10 | H2 | EI | Franklin and Carroll, 1969 | RDSH |
C6H6+ | 9.88 ± 0.10 | H2 | EI | Franklin and Carroll, 1969 | RDSH |
C6H7+ | 10.45 | H | PIPECO | Lias and Ausloos, 1985 | LBLHLM |
C6H7+ | 10.82 ± 0.10 | H | EI | Franklin and Carroll, 1969 | RDSH |
De-protonation reactions
C6H7- + =
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 373.2 ± 4.1 | kcal/mol | G+TS | Lee and Squires, 1986 | gas phase; Between SiH4, tBuOH; value altered from reference due to change in acidity scale; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 365.8 ± 4.0 | kcal/mol | IMRB | Lee and Squires, 1986 | gas phase; Between SiH4, tBuOH; value altered from reference due to change in acidity scale; B |
Mass spectrum (electron ionization)
Go To: Top, Condensed phase thermochemistry data, Phase change 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 | NIST Mass Spectrometry Data Center, 1990. |
NIST MS number | 118700 |
References
Go To: Top, Condensed phase thermochemistry data, Phase change 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.
Steele, Chirico, et al., 1989
Steele, W.V.; Chirico, R.D.; Nguyen, A.; Hossenlopp, I.A.; Smith, N.K.,
Determination of some pure compound ideal-gas enthalpies of formation,
AIChE Symp. Ser., 1989, 85, 140-162. [all data]
Geipel and Wolf, 1976
Geipel, G.; Wolf, G.,
Die molare Wärmekapazität von Cyclohexadien(1,4) und Cyclohexadien(1,3) im Temperaturegebiet von 10...300K,
Z. Phys. Chem., 1976, 257, 587-593. [all data]
White and Bishop, 1940
White, A.H.; Bishop, W.S.,
Dielectric Evidence of Molecular Rotation in the Crystals of Certain Non-aromatic Compounds,
J. Am. Chem. Soc., 1940, 62, 8-16. [all data]
Kistiakowsky, Ruhoff, et al., 1936
Kistiakowsky, G.B.; Ruhoff, J.R.; Smith, H.A.; Vaughan, W.E.,
Heats of Organic Reactions IV. Hydrogenation of Some Dienes and of Benzene,
J. Am. Chem. Soc., 1936, 58, 146-53. [all data]
Geipel and Wolf, 1976, 2
Geipel, G.; Wolf, G.,
Molar Heat Capacity of Cyclohexadiene(1,4) and Cyclohexadiene(1,3) in Temperature Range of 10... 300K,
Z. Phys. Chem. (Leipzig), 1976, 257, 587. [all data]
Rogers, 1972
Rogers, F.E.,
Thermochemistry of the Diels-Alder reactions. II. Heat of addition of several dienes to tetracyanoethylene,
J. Phys. Chem., 1972, 76, 106-109. [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]
Meyer and Hotz, 1973
Meyer, Edwin F.; Hotz, Roger D.,
High-precision vapor-pressure data for eight organic compounds,
J. Chem. Eng. Data, 1973, 18, 4, 359-362, https://doi.org/10.1021/je60059a008
. [all data]
Letcher and Marsicano, 1974
Letcher, T.M.; Marsicano, F.,
Vapour pressures and densities of some unsaturated C6 acyclic and cyclic hydrocarbons between 300 and 320 K,
The Journal of Chemical Thermodynamics, 1974, 6, 5, 509-514, https://doi.org/10.1016/0021-9614(74)90013-5
. [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]
Hunter and Lias, 1998
Hunter, E.P.; Lias, S.G.,
Evaluated Gas Phase Basicities and Proton Affinities of Molecules: An Update,
J. Phys. Chem. Ref. Data, 1998, 27, 3, 413-656, https://doi.org/10.1063/1.556018
. [all data]
Kimura, Katsumata, et al., 1981
Kimura, K.; Katsumata, S.; Achiba, Y.; Yamazaki, T.; Iwata, S.,
Ionization energies, Ab initio assignments, and valence electronic structure for 200 molecules
in Handbook of HeI Photoelectron Spectra of Fundamental Organic Compounds, Japan Scientific Soc. Press, Tokyo, 1981. [all data]
Bieri, Burger, et al., 1977
Bieri, G.; Burger, F.; Heilbronner, E.; Maier, J.P.,
Valence ionization enrgies of hydrocarbons,
Helv. Chim. Acta, 1977, 60, 2213. [all data]
Demeo and El-Sayed, 1970
Demeo, D.A.; El-Sayed, M.A.,
Ionization potential and structure of olefins,
J. Chem. Phys., 1970, 52, 2622. [all data]
Bischof and Heilbronner, 1970
Bischof, P.; Heilbronner, E.,
Photoelektron-Spektren von Cycloalkenen und Cycloalkadienen,
Helv. Chim. Acta, 1970, 53, 1677. [all data]
Franklin and Carroll, 1969
Franklin, J.L.; Carroll, S.R.,
Effect of molecular structure on ionic decomposition. II. An electron-impact study of 1,3-and 1,4-cyclohexadiene and 1,3,5-hexatriene,
J. Am. Chem. Soc., 1969, 91, 6564. [all data]
Worley, Webb, et al., 1979
Worley, S.D.; Webb, T.R.; Gibson, D.H.; Ong, T.-S.,
On the electronic structures of cyclobutadiene trimethylenemethane,
J. Organomet. Chem., 1979, 168, 16. [all data]
Heilbronner, Hoshi, et al., 1976
Heilbronner, E.; Hoshi, T.; von Rosenberg, J.L.; Hafner, K.,
Alkyl-induced, natural hypsochromic shifts of the 2A←2X and 2B←2X transitions of azulene and naphthalene radical cations,
Nouv. J. Chim., 1976, 1, 105. [all data]
Lias and Ausloos, 1985
Lias, S.G.; Ausloos, P.,
Structures of C6H7+ ions formed in unimolecular and bimolecular reactions,
J. Chem. Phys., 1985, 82, 3613. [all data]
Lee and Squires, 1986
Lee, R.E.; Squires, R.R.,
Anionic homoaromaticity: A gas phase experimental study,
J. Am. Chem. Soc., 1986, 105, 5078. [all data]
Notes
Go To: Top, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, Mass spectrum (electron ionization), References
- Symbols used in this document:
AE Appearance energy Cp,liquid Constant pressure heat capacity of liquid S°liquid Entropy of liquid at standard conditions Tboil Boiling point Tfus Fusion (melting) point Ttriple Triple point temperature ΔcH°liquid Enthalpy of combustion of liquid at standard conditions ΔfH°liquid Enthalpy of formation 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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