Ethanone, 1,1'-(1,4-phenylene)bis-

Formula: C₁₀H₁₀O₂
Molecular weight: 162.1852
IUPAC Standard InChI: InChI=1S/C10H10O2/c1-7(11)9-3-5-10(6-4-9)8(2)12/h3-6H,1-2H3
IUPAC Standard InChIKey: SKBBQSLSGRSQAJ-UHFFFAOYSA-N
CAS Registry Number: 1009-61-6
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: Benzene, p-diacetyl-; p-Acetylacetophenone; p-Diacetylbenzene; 1,4-Diacetylbenzene
Permanent link for this species. Use this link for bookmarking this species for future reference.
Information on this page:
Other data available:
- IR Spectrum
- Mass spectrum (electron ionization)
Options:
- Switch to calorie-based units

Phase change data

Go To: Top, Gas phase ion energetics data, Gas Chromatography, References, Notes

Data compiled by: William E. Acree, Jr., James S. Chickos

Enthalpy of vaporization

Δ_vapH (kJ/mol)	Temperature (K)	Method	Reference	Comment
82.2	403.	A	Stephenson and Malanowski, 1987	Based on data from 388. to 431. K.

Gas phase ion energetics data

Go To: Top, Phase change data, Gas Chromatography, References, Notes

Data evaluated as indicated in comments:
HL - Edward P. Hunter and 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
B - John E. Bartmess

Quantity	Value	Units	Method	Reference	Comment
Proton affinity (review)	850.8	kJ/mol	N/A	Hunter and Lias, 1998	HL
Quantity	Value	Units	Method	Reference	Comment
Gas basicity	821.0	kJ/mol	N/A	Hunter and Lias, 1998	HL

Electron affinity determinations

EA (eV)	Method	Reference	Comment
1.062 ± 0.087	IMRE	Mishima, Huh, et al., 1995	ΔGea(343 K)=-25.4 kcal/mol. Reanchored to EA(PhNO2), Kebarle and Chowdhury, 1987.; B
1.041 ± 0.087	IMRE	Huh, Kang, et al., 1999	ΔG(EA) 343K; anchored to ΔG value. Including anchor ΔS, EA is ca. 0.4 kcal/mol more bound.; B

Ionization energy determinations

IE (eV)	Method	Reference	Comment
9.61	PE	Gal, Geribaldi, et al., 1985	Vertical value; LBLHLM

Gas Chromatography

Go To: Top, Phase change data, Gas phase ion energetics data, References, Notes

Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director

Van Den Dool and Kratz RI, non-polar column, temperature ramp

View large format table.

Column type	Active phase	I	Reference	Comment
Capillary	DB-5	1470.	Guichard and Souty, 1988	H2, 30. C @ 5. min, 1.5 K/min; Column length: 0.32 m; Column diameter: 1. mm; T_end: 180. C

Normal alkane RI, non-polar column, temperature ramp

View large format table.

Column type	Active phase	I	Reference	Comment
Capillary	SPB-5	1451.	Sebastian, Viallon-Fernandez, et al., 2003	60. m/0.32 mm/1.0 μm, Helium, 3. K/min; T_start: 30. C; T_end: 230. C

References

Go To: Top, Phase change data, Gas phase ion energetics data, Gas Chromatography, Notes

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]

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]

Mishima, Huh, et al., 1995
Mishima, M.; Huh, C.; Lee, H.W.; Nakamura, H.; Fujio, M.; Tsuno, Y., Electron affinities of acetophenones and methyl benzoates. Varying resonance demand of aromatic radical anions, Tetrahed. Lett., 1995, 36, 13, 2265, https://doi.org/10.1016/0040-4039(95)00267-G . [all data]

Kebarle and Chowdhury, 1987
Kebarle, P.; Chowdhury, S., Electron affinities and electron transfer reactions, Chem. Rev., 1987, 87, 513. [all data]

Huh, Kang, et al., 1999
Huh, C.; Kang, C.H.; Lee, H.W.; Nakamura, H.; Mishima, M.; Tsuno, Y.; Yamataka, H., Thermodynamic stabilities and resonance demand of aromatic radical anions in the gas phase, Bull. Chem. Soc. Japan, 1999, 72, 5, 1083-1091, https://doi.org/10.1246/bcsj.72.1083 . [all data]

Gal, Geribaldi, et al., 1985
Gal, J.-F.; Geribaldi, S.; Pfister-Guillouzo, G.; Morris, D.G., Basicity of the carbonyl group. Part 12. Correlations between ionization potentials and lewis basicities in aromatic carbonyl compounds, J. Chem. Soc. Perkin Trans. 2, 1985, 103. [all data]

Guichard and Souty, 1988
Guichard, E.; Souty, M., Comparison of the relative quantities of aroma compounds found in fresh apricot (Prunus armeniaca) from six different varieties, Z. Lebensm. Unters. Forsch., 1988, 186, 4, 301-307, https://doi.org/10.1007/BF01027031 . [all data]

Sebastian, Viallon-Fernandez, et al., 2003
Sebastian, I.; Viallon-Fernandez, C.; Berge, P.; Berdague, J.-L., Analysis of the volatile fraction of lamb fat tissue: influence of the type of feeding, Sciences des Aliments, 2003, 23, 4, 497-511, https://doi.org/10.3166/sda.23.497-511 . [all data]

Notes

Go To: Top, Phase change data, Gas phase ion energetics data, Gas Chromatography, References

Symbols used in this document:

EA Electron affinity

Δ_vapH Enthalpy of vaporization
Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
The National Institute of Standards and Technology (NIST) uses its best efforts to deliver a high quality copy of the Database and to verify that the data contained therein have been selected on the basis of sound scientific judgment. However, NIST makes no warranties to that effect, and NIST shall not be liable for any damage that may result from errors or omissions in the Database.
Customer support for NIST Standard Reference Data products.