1,4-Cyclohexanedione

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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
Δfgas-332.6 ± 1.2kJ/molCcbPilcher, Parchment, et al., 1993 

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
Δfsolid-407.6 ± 1.0kJ/molCcbPilcher, Parchment, et al., 1993ALS
Quantity Value Units Method Reference Comment
Δcsolid-3096.8 ± 0.6kJ/molCcbPilcher, Parchment, et al., 1993Corresponding Δfsolid = -407.6 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS

Constant pressure heat capacity of solid

Cp,solid (J/mol*K) Temperature (K) Reference Comment
161.4300.DeWit, DeKruif, et al., 1983T = 90 to 310 K. Linearly extrapolated.; 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:
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
DH - Eugene S. Domalski and Elizabeth D. Hearing
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

Quantity Value Units Method Reference Comment
Tfus350.KN/AAlvik, Borgen, et al., 1972Crystal phase 1 phase; Uncertainty assigned by TRC = 1. K; TRC
Tfus351.15KN/AHartley and Dobbie, 1898Uncertainty assigned by TRC = 1. K; TRC
Quantity Value Units Method Reference Comment
Ttriple351.6KN/ADe Wit, De Kruif, et al., 1983Crystal phase 1 phase; Uncertainty assigned by TRC = 0.2 K; TRC
Quantity Value Units Method Reference Comment
Δsub75.0 ± 1.0kJ/molVPilcher, Parchment, et al., 1993ALS
Δsub75.0 ± 1.0kJ/molCPilcher, Parchment, et al., 1993AC
Δsub84.2kJ/molN/ADe Wit, Van Miltenburg, et al., 1983AC

Enthalpy of sublimation

ΔsubH (kJ/mol) Temperature (K) Method Reference Comment
75.000298.15N/APilcher, Parchment, et al., 1993DH
84.4289.TE,MEDe Wit, Van Miltenburg, et al., 1983AC

Enthalpy of fusion

ΔfusH (kJ/mol) Temperature (K) Reference Comment
11.26351.5De Wit, De Kruif, et al., 1983, 2AC
10.04348.2Alvik, Borgen, et al., 1972, 2AC

Entropy of fusion

ΔfusS (J/mol*K) Temperature (K) Reference Comment
19.09322.2Alvik, Borgen, et al., 1972CAL
2.83339.2
28.84348.2

Temperature of phase transition

Ttrs (K) Initial Phase Final Phase Reference Comment
319.89crystaline, IIIcrystaline, IIDeWit, DeKruif, et al., 1983DH
336.73crystaline, IIcrystaline, IDeWit, DeKruif, et al., 1983DH

Enthalpy of phase transition

ΔHtrs (kJ/mol) Temperature (K) Initial Phase Final Phase Reference Comment
11.325351.6crystaline, IliquidDeWit, DeKruif, et al., 1983DH

In addition to the Thermodynamics Research Center (TRC) data available from this site, much more physical and chemical property data is available from the following TRC products:


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 evaluated as indicated in comments:
HL - Edward P. Hunter and Sharon G. Lias

Data compiled as indicated in comments:
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi

View reactions leading to C6H8O2+ (ion structure unspecified)

Quantity Value Units Method Reference Comment
Proton affinity (review)812.5kJ/molN/AHunter and Lias, 1998HL
Quantity Value Units Method Reference Comment
Gas basicity782.7kJ/molN/AHunter and Lias, 1998HL

Ionization energy determinations

IE (eV) Method Reference Comment
9.85PEDougherty, Brint, et al., 1978Vertical value; LLK
9.65PECowan, Gleiter, et al., 1971Vertical value; LLK

IR Spectrum

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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

Gas Phase Spectrum

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IR spectrum
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Additional Data

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Owner NIST Standard Reference Data Program
Collection (C) 2018 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
State gas
Instrument HP-GC/MS/IRD

This IR spectrum is from the NIST/EPA Gas-Phase Infrared Database .


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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Mass spectrum
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Additional Data

View image of digitized spectrum (can be printed in landscape orientation).

Due to licensing restrictions, this spectrum cannot be downloaded.

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 150869

All mass spectra in this site (plus many more) are available from the NIST/EPA/NIH Mass Spectral Library. Please see the following for information about the library and its accompanying search program.


References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, IR Spectrum, 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.

Pilcher, Parchment, et al., 1993
Pilcher, G.; Parchment, O.G.; Hillier, I.H.; Heatley, F.; Fletcher, D.; Ribeiro da Silva, M.A.V.; Ferrao, M.L.C.C.H.; Monte, J.S.; Jiye, F., Thermochemical and theoretical studies on cyclohexanediones, J. Phys. Chem., 1993, 97, 243-247. [all data]

DeWit, DeKruif, et al., 1983
DeWit, H.G.M.; DeKruif, C.G.; Van Miltenburg, J.C., Thermodynamic properties of molecular organic crystals containing organic crystals containing nitrogen, oxygen, and sulfur. II. Molar heat capacities of eight compounds by adiabatic calorimetry, J. Chem. Thermodynam., 1983, 15, 891-902. [all data]

Alvik, Borgen, et al., 1972
Alvik, T.; Borgen, G.; Dale, J., Conformational Studies of Normal, Medium, and Large Ring Diametric Cycloalkanediones and Their Ethylene Ketal Derivatives., Acta Chem. Scand., 1972, 26, 1805, https://doi.org/10.3891/acta.chem.scand.26-1805 . [all data]

Hartley and Dobbie, 1898
Hartley, W.N.; Dobbie, J.J., The ultraviolet absorption spectra of some closed chain carbon compounds, J. Chem. Soc., 1898, 73, 598. [all data]

De Wit, De Kruif, et al., 1983
De Wit, H.G.M.; De Kruif, C.G.; Van Miltenburg, J.C., Thermodynamic properties of molecular organic crystals containing nitrogen, oxygen, and sulfur II. Molar heat capacities of eight compounds by adiabatic calorimetry, J. Chem. Thermodyn., 1983, 15, 9, 891, https://doi.org/10.1016/0021-9614(83)90095-2 . [all data]

De Wit, Van Miltenburg, et al., 1983
De Wit, H.G.M.; Van Miltenburg, J.C.; De Kruif, C.G., Thermodynamic properties of molecular organic crystals containing nitrogen, oxygen, and sulphur 1. Vapour pressures and enthalpies of sublimation, The Journal of Chemical Thermodynamics, 1983, 15, 7, 651-663, https://doi.org/10.1016/0021-9614(83)90079-4 . [all data]

De Wit, De Kruif, et al., 1983, 2
De Wit, H.G.M.; De Kruif, C.G.; Van Miltenburg, J.C., Thermodynamic properties of molecular organic crystals containing nitrogen, oxygen, and sulfur II. Molar heat capacities of eight compounds by adiabatic calorimetry, The Journal of Chemical Thermodynamics, 1983, 15, 9, 891-902, https://doi.org/10.1016/0021-9614(83)90095-2 . [all data]

Alvik, Borgen, et al., 1972, 2
Alvik, Thor; Borgen, Gerd; Dale, Johannes; Øye, H.A.; Svensson, Sigfrid, Conformational Studies of Normal, Medium, and Large Ring Diametric Cycloalkanediones and Their Ethylene Ketal Derivatives., Acta Chem. Scand., 1972, 26, 1805-1816, https://doi.org/10.3891/acta.chem.scand.26-1805 . [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]

Dougherty, Brint, et al., 1978
Dougherty, D.; Brint, P.; McGlynn, S.P., Photoelectron spectroscopy of carbonyls. Lone-pair interactions in α-, β-, γ δ-dicarbonyls, J. Am. Chem. Soc., 1978, 100, 5597. [all data]

Cowan, Gleiter, et al., 1971
Cowan, D.O.; Gleiter, R.; Hashmall, J.A.; Heilbronner, E.; Hornung, V., Interaction between the orbitals of lone pair electrons in dicarbonyl compounds, Angew. Chem. Int. Ed. Engl., 1971, 10, 401. [all data]


Notes

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), References