p-Benzoquinone
- Formula: C6H4O2
- Molecular weight: 108.0948
- IUPAC Standard InChI: InChI=1S/C6H4O2/c7-5-1-2-6(8)4-3-5/h1-4H
- IUPAC Standard InChIKey: AZQWKYJCGOJGHM-UHFFFAOYSA-N
- CAS Registry Number: 106-51-4
- 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: 2,5-Cyclohexadiene-1,4-dione; p-Quinone; Chinone; Quinone; 1,4-Benzoquinone; 1,4-Cyclohexadienedione; Benzoquinone; Benzo-chinon; Chinon; Cyclohexadienedione; NCI-C55845; 1,4-Benzoquine; 1,4-Cyclohexadiene dioxide; 1,4-Diossibenzene; 1,4-Dioxy-benzol; p-Chinon; Rcra waste number U197; UN 2587; USAF P-220; Steara PBQ; NSC 36324
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Gas phase ion energetics data
Go To: Top, Gas Chromatography, 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
L - Sharon G. Lias
Data compiled as indicated in comments:
LBLHLM - Sharon G. Lias, John E. Bartmess, Joel F. Liebman, John L. Holmes, Rhoda D. Levin, and W. Gary Mallard
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron
B - John E. Bartmess
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| IE (evaluated) | 10.0 ± 0.1 | eV | N/A | N/A | L |
| Quantity | Value | Units | Method | Reference | Comment |
| Proton affinity (review) | 191.0 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
| Quantity | Value | Units | Method | Reference | Comment |
| Gas basicity | 183.9 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
Electron affinity determinations
| EA (eV) | Method | Reference | Comment |
|---|---|---|---|
| 1.850 ± 0.010 | LPES | Fu, Yang, et al., 2011 | Triplet state of neutral 2.32 eV up; B |
| 1.8600 ± 0.0050 | LPES | Schiedt and Weinkauf, 1999 | Neutral T1 state is 2.3 eV up: Siegert, Vogeler, et al., 20112; B |
| 1.91 ± 0.10 | TDEq | Heinis, Chowdhury, et al., 1988 | ΔGea(423 K) = -42.4 kcal/mol; ΔSea = -4.0 eu.; B |
| 1.930 ± 0.048 | IMRE | Fukuda and McIver, 1985 | ΔGea(355 K) = -43.1 kcal/mol; ΔSea =-4.0, est. from data in Heinis, Chowdhury, et al., 1988; B |
| 1.990 ± 0.048 | LPD | Marks, Comita, et al., 1985 | B |
| 1.89 ± 0.30 | NBIE | Cooper, Naff, et al., 1975 | B |
| 1.370 ± 0.078 | SI | Farragher and Page, 1966 | The Magnetron method, lacking mass analysis, is not considered reliable.; B |
Ionization energy determinations
| IE (eV) | Method | Reference | Comment |
|---|---|---|---|
| 10.11 | PE | Lauer, Schafer, et al., 1975 | LLK |
| 10.01 | PE | Kobayashi, 1975 | LLK |
| 9.96 ± 0.01 | PI | Kotov and Potapov, 1972 | LLK |
| 9.96 ± 0.01 | PI | Potapov and Sorokin, 1971 | LLK |
| 9.95 | PE | Dewar and Worley, 1969 | RDSH |
| 9.7 | PI | Terenin, 1961 | RDSH |
| 9.67 ± 0.02 | PI | Vilesov and Terenin, 1957 | RDSH |
| 10.1 | PE | Bock, Mohmand, et al., 1983 | Vertical value; LBLHLM |
| 9.99 ± 0.05 | PE | Dougherty and McGlynn, 1977 | Vertical value; LLK |
| 10.03 | PE | Cowan, Gleiter, et al., 1971 | Vertical value; LLK |
Appearance energy determinations
| Ion | AE (eV) | Other Products | Method | Reference | Comment |
|---|---|---|---|---|---|
| C4H2O2+ | 11.2 ± 0.05 | C2H2 | PI | Potapov and Sorokin, 1971 | LLK |
| C5H4O+ | 11.10 ± 0.05 | CO | PI | Potapov and Sorokin, 1971 | LLK |
Gas Chromatography
Go To: Top, 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
Kovats' RI, non-polar column, isothermal
| Column type | Active phase | Temperature (C) | I | Reference | Comment |
|---|---|---|---|---|---|
| Packed | SE-30 | 180. | 905. | Llobera and García-Raso, 1987 | N2, Chromosorb P AW DMCS; Column length: 2. m |
| Packed | SE-30 | 190. | 912. | Llobera and García-Raso, 1987 | N2, Chromosorb P AW DMCS; Column length: 2. m |
| Packed | SE-30 | 200. | 919. | Llobera and García-Raso, 1987 | N2, Chromosorb P AW DMCS; Column length: 2. m |
| Packed | SE-30 | 210. | 923. | Llobera and García-Raso, 1987 | N2, Chromosorb P AW DMCS; Column length: 2. m |
Kovats' RI, polar column, isothermal
| Column type | Active phase | Temperature (C) | I | Reference | Comment |
|---|---|---|---|---|---|
| Packed | Carbowax 20M | 180. | 1562. | Llobera and García-Raso, 1987 | N2, Chromosorb P AW DMCS (60-80 mesh); Column length: 2. m |
| Packed | Carbowax 20M | 190. | 1570. | Llobera and García-Raso, 1987 | N2, Chromosorb P AW DMCS (60-80 mesh); Column length: 2. m |
| Packed | Carbowax 20M | 200. | 1579. | Llobera and García-Raso, 1987 | N2, Chromosorb P AW DMCS (60-80 mesh); Column length: 2. m |
| Packed | Carbowax 20M | 210. | 1587. | Llobera and García-Raso, 1987 | N2, Chromosorb P AW DMCS (60-80 mesh); Column length: 2. m |
Normal alkane RI, non-polar column, temperature ramp
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | OV-101 | 888. | Zenkevich, 2005 | 25. m/0.20 mm/0.10 μm, N2/He, 6. K/min; Tstart: 50. C; Tend: 250. C |
Lee's RI, non-polar column, temperature ramp
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | DB-5MS | 143.19 | Chen, Keeran, et al., 2002 | 30. m/0.25 mm/0.5 μm, 40. C @ 1. min, 10. K/min; Tend: 310. C |
| Capillary | DB-5MS | 147.33 | Chen, Keeran, et al., 2002 | 30. m/0.25 mm/0.5 μm, 40. C @ 1. min, 4. K/min; Tend: 310. C |
References
Go To: Top, Gas phase ion energetics data, Gas Chromatography, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
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]
Fu, Yang, et al., 2011
Fu, Q.A.; Yang, J.L.; Wang, X.B.,
On the Electronic Structures and Electron Affinities of the m-Benzoquinone (BQ) Diradical and the o-, p-BQ Molecules: A Synergetic Photoelectron Spectroscopic and Theoretical Study,
J. Phys. Chem. A, 2011, 115, 15, 3201-3207, https://doi.org/10.1021/jp1120542
. [all data]
Schiedt and Weinkauf, 1999
Schiedt, J.; Weinkauf, R.,
Resonant Photodetachment via Shape and Feshbach Resonances: p-Benzoquinone Anions as a Model System,
J. Chem. Phys., 1999, 110, 1, 304, https://doi.org/10.1063/1.478066
. [all data]
Siegert, Vogeler, et al., 2011
Siegert, S.; Vogeler, F.; Marian, C.M.; Weinkauf, R.,
Throwing light on dark states of alpha-oligothiophenes of chain lengths 2 to 6: radical anion photoelectron spectroscopy and excited-state theory,
Phys. Chem. Chem. Phys., 2011, 13, 21, 10350-10363, https://doi.org/10.1039/c0cp02712j
. [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]
Marks, Comita, et al., 1985
Marks, J.; Comita, P.B.; Brauman, J.I.,
Threshold resonances in electron photodetachment spectra. Structural evidence for dipole-supported states,
J. Am. Chem. Soc., 1985, 107, 3718. [all data]
Cooper, Naff, et al., 1975
Cooper, C.D.; Naff, W.T.; Compton, R.N.,
Negative ion properties of p-benzoquinone: Electron affinity and compound states,
J. Chem. Phys., 1975, 63, 2752. [all data]
Farragher and Page, 1966
Farragher, A.L.; Page, F.M.,
Experimental Determination of Electron Affinities. Part 9. - Benzoquinone, Chloranil and Related Compounds,
Trans. Farad. Soc., 1966, 62, 3072, https://doi.org/10.1039/tf9666203072
. [all data]
Lauer, Schafer, et al., 1975
Lauer, G.; Schafer, W.; Schweig, A.,
Assignment of the four lowest ionized states of p-benzoquinone and the question of "lone pair" splitting in this system,
Chem. Phys. Lett., 1975, 33, 312. [all data]
Kobayashi, 1975
Kobayashi, T.,
Photoelectron spectra of p-benzoquinones,
J. Electron. Spectrosc. Relat. Phenom., 1975, 7, 349. [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]
Dewar and Worley, 1969
Dewar, M.J.S.; Worley, S.D.,
Photoelectron spectra of molecules. I. Ionization potentials of some organic molecules and their interpretation,
J. Chem. Phys., 1969, 50, 654. [all data]
Terenin, 1961
Terenin, A.,
Charge transfer in organic solids, induced by light,
Proc. Chem. Soc., London, 1961, 321. [all data]
Vilesov and Terenin, 1957
Vilesov, F.I.; Terenin, A.N.,
The photoionization of the vapors of certain organic compounds,
Dokl. Akad. Nauk SSSR, 1957, 115, 744, In original 539. [all data]
Bock, Mohmand, et al., 1983
Bock, H.; Mohmand, S.; Hirabayashi, T.; Maier, G.; Reisenauer, H.P.,
Photoelektronen-spektroskopischer nachweis und matrix-isolierung von thio-para-benzochinonen,
Chem. Ber., 1983, 116, 273. [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]
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]
Llobera and García-Raso, 1987
Llobera, A.; García-Raso, A.,
Gas chromatographic behaviour of several p-quinones,
J. Chromatogr., 1987, 393, 2, 305-311, https://doi.org/10.1016/S0021-9673(01)94227-X
. [all data]
Zenkevich, 2005
Zenkevich, I.G.,
Experimentally measured retention indices., 2005. [all data]
Chen, Keeran, et al., 2002
Chen, P.H.; Keeran, W.S.; Van Ausdale, W.A.; Schindler, D.R.; Roberts, D.W.,
Application of Lee retention indices to the confirmation of tentatively identified compounds from GC/MS analysis of environmental samples, Technical paper, Analytical Services Division, Environmental ScienceEngineering, Inc, PO Box 1703, Gainesville, FL 32602, 2002, 11. [all data]
Notes
Go To: Top, Gas phase ion energetics data, Gas Chromatography, References
- Symbols used in this document:
AE Appearance energy EA Electron affinity IE (evaluated) Recommended ionization energy - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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