Duroquinone
- Formula: C10H12O2
- Molecular weight: 164.2011
- IUPAC Standard InChIKey: WAMKWBHYPYBEJY-UHFFFAOYSA-N
- CAS Registry Number: 527-17-3
- 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: p-Benzoquinone, 2,3,5,6-tetramethyl-; 2,5-Cyclohexadiene-1,4-dione, 2,3,5,6-tetramethyl-; Tetramethyl-p-benzoquinone; Tetramethyl-1,4-benzoquinone; Tetramethylquinone; 2,3,5,6-Tetramethyl-p-benzoquinone; 2,3,5,6-Tetramethyl-1,4-benzoquinone; 2,3,5,6-Tetramethylbenzoquinone; Tetramethyl-p-quinone; p-Benzoquinone, tetramethyl-; 2,3,5,6-Tetramethyl-2,5-cyclohexadiene-1,4-dione; NSC 2068; p-Benzoquinone, tetramethyl-, semiquinone
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Phase change data
Go To: Top, Gas phase ion energetics data, IR Spectrum, 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:
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
AC - William E. Acree, Jr., James S. Chickos
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tfus | 380. | K | N/A | Smith and Dobrovolny, 1926 | Uncertainty assigned by TRC = 2. K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔsubH° | 22.3 ± 0.29 | kcal/mol | DSC | Rojas-Aguilar, Flores-Lara, et al., 2004 | AC |
Enthalpy of fusion
ΔfusH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
4.40 ± 0.02 | 384.1 | DSC | Rojas-Aguilar, Flores-Lara, et al., 2004 | AC |
4.43 ± 0.02 | 384.8 | HFC | Rojas-Aguilar, Flores-Lara, et al., 2004 | AC |
Gas phase ion energetics data
Go To: Top, Phase change data, IR Spectrum, 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:
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
B - John E. Bartmess
Electron affinity determinations
EA (eV) | Method | Reference | Comment |
---|---|---|---|
1.622 ± 0.061 | TDEq | Heinis, Chowdhury, et al., 1988 | ΔGea(423 K) = -36.0 kcal/mol; ΔSea = -3.2 eu.; B |
1.604 ± 0.048 | IMRE | Fukuda and McIver, 1985 | ΔGea(355 K) = -35.9 kcal/mol; ΔSea =-3.2, est. from data in Heinis, Chowdhury, et al., 1988; B |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
9.1 | PE | Bock, Kaim, et al., 1980 | LLK |
9.16 ± 0.03 | PI | Kotov and Potapov, 1972 | LLK |
9.16 ± 0.03 | PI | Potapov and Sorokin, 1971 | LLK |
9.25 ± 0.05 | PE | Dougherty and McGlynn, 1977 | Vertical value; LLK |
Appearance energy determinations
Ion | AE (eV) | Other Products | Method | Reference | Comment |
---|---|---|---|---|---|
C9H12O+ | 10.1 ± 0.05 | CO | PI | Potapov and Sorokin, 1971 | LLK |
IR Spectrum
Go To: Top, 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
Gas Phase Spectrum
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Notice: Concentration information is not available for this spectrum and, therefore, molar absorptivity values cannot be derived.
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 |
References
Go To: Top, Phase change data, Gas phase ion energetics data, IR Spectrum, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Smith and Dobrovolny, 1926
Smith, L.I.; Dobrovolny, F.J.,
Duroquinone and Some Derivatives of Durene,
J. Am. Chem. Soc., 1926, 48, 1420-23. [all data]
Rojas-Aguilar, Flores-Lara, et al., 2004
Rojas-Aguilar, Aarón; Flores-Lara, Honorio; Martinez-Herrera, Melchor; Ginez-Carbajal, Francisco,
Thermochemistry of benzoquinones,
The Journal of Chemical Thermodynamics, 2004, 36, 6, 453-463, https://doi.org/10.1016/j.jct.2004.03.002
. [all data]
Heinis, Chowdhury, et al., 1988
Heinis, T.; Chowdhury, S.; Scott, S.L.; Kebarle, P.,
Electron Affinities of Benzo-, Naphtho-, and Anthraquinones Determined from Gas-Phase Equilibria Measurements,
J. Am. Chem. Soc., 1988, 110, 2, 400, https://doi.org/10.1021/ja00210a015
. [all data]
Fukuda and McIver, 1985
Fukuda, E.K.; McIver, R.T., Jr.,
Relative electron affinities of substituted benzophenones, nitrobenzenes, and quinones. [Anchored to EA(SO2) from 74CEL/BEN],
J. Am. Chem. Soc., 1985, 107, 2291. [all data]
Bock, Kaim, et al., 1980
Bock, H.; Kaim, W.; Timms, P.L.; Hawker, P.,
Durosemiquinone and its BF analogue - detection of 1,4-diborine as an unexpected elimination product,
Chem. Ber., 1980, 113, 3196. [all data]
Kotov and Potapov, 1972
Kotov, B.V.; Potapov, V.K.,
Ionization potentials of strong organic electron acceptors,
Khim. Vys. Energ., 1972, 6, 375. [all data]
Potapov and Sorokin, 1971
Potapov, V.K.; Sorokin, V.V.,
Photoionization and ion-molecule reactions in quinones and alcohols,
High Energy Chem., 1971, 5, 435, In original 487. [all data]
Dougherty and McGlynn, 1977
Dougherty, D.; McGlynn, S.P.,
Photoelectron spectroscopy of carbonyls. 1,4-Benzoquinones,
J. Am. Chem. Soc., 1977, 99, 3234. [all data]
Notes
Go To: Top, Phase change data, Gas phase ion energetics data, IR Spectrum, References
- Symbols used in this document:
AE Appearance energy EA Electron affinity Tfus Fusion (melting) point ΔfusH Enthalpy of fusion ΔsubH° Enthalpy of sublimation at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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