3-Pentanone, 2,2,4,4-tetramethyl-
- Formula: C9H18O
- Molecular weight: 142.2386
- IUPAC Standard InChIKey: UIQGEWJEWJMQSL-UHFFFAOYSA-N
- CAS Registry Number: 815-24-7
- 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: Di-tert-butyl ketone; Hexamethylacetone; Pivalone; 2,2,4,4-Tetramethyl-3-pentanone; (t-C4H9)2CO; 2,2,4,4-Tetramethyl-pentan-3-one
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Gas phase thermochemistry data
Go To: Top, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, Mass spectrum (electron ionization), UV/Visible spectrum, 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 compiled by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°gas | -345.8 ± 1.2 | kJ/mol | Ccr | Seller, 1970 |
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 by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°liquid | -391.2 ± 1.2 | kJ/mol | Ccr | Seller, 1970 | |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°liquid | -5722.9 ± 1.1 | kJ/mol | Ccr | Seller, 1970 | Corresponding ΔfHºliquid = -391.15 kJ/mol (simple calculation by NIST; no Washburn corrections) |
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
AC - William E. Acree, Jr., James S. Chickos
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tboil | 425. ± 3. | K | AVG | N/A | Average of 10 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 247.91 | K | N/A | Howard, Mears, et al., 1947 | Uncertainty assigned by TRC = 0.1 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 45.5 ± 0.4 | kJ/mol | C | Peacock and Fuchs, 1977 | AC |
ΔvapH° | 45.35 ± 0.09 | kJ/mol | C | Seller, 1970 | ALS |
ΔvapH° | 45.4 ± 0.1 | kJ/mol | C | Seller, 1970 | AC |
ΔvapH° | 45.4 ± 0.1 | kJ/mol | C | Wadsö, Murto, et al., 1966 | AC |
ΔvapH° | 45.40 ± 0.08 | kJ/mol | C | Wadso, 1966 | ALS |
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
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Proton affinity (review) | 861.3 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
Quantity | Value | Units | Method | Reference | Comment |
Gas basicity | 831.5 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
8.67 ± 0.02 | PE | Hernandez, Masclet, et al., 1977 | LLK |
8.67 ± 0.01 | PE | Mouvier and Hernandez, 1975 | LLK |
8.79 ± 0.05 | EI | Mouvier and Hernandez, 1975 | LLK |
8.71 ± 0.02 | PE | Cocksey, Eland, et al., 1971 | LLK |
8.65 ± 0.03 | PI | Vilesov, 1960 | RDSH |
Appearance energy determinations
Ion | AE (eV) | Other Products | Method | Reference | Comment |
---|---|---|---|---|---|
C5H9O+ | ~9.38 | ? | EI | Mouvier and Hernandez, 1975 | LLK |
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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Additional Data
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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 | 156453 |
UV/Visible 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.
Spectrum
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Additional Data
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Source | Hayes, 1966 |
---|---|
Owner | INEP CP RAS, NIST OSRD Collection (C) 2007 copyright by the U.S. Secretary of Commerce on behalf of the United States of America. All rights reserved. |
Origin | INSTITUTE OF ENERGY PROBLEMS OF CHEMICAL PHYSICS, RAS |
Source reference | RAS UV No. 19936 |
Instrument | Hilger Uvispek |
Boiling point | 152 |
Gas Chromatography
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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
Kovats' RI, non-polar column, isothermal
Column type | Active phase | Temperature (C) | I | Reference | Comment |
---|---|---|---|---|---|
Capillary | OV-1 | 333. | 900. | Hu, Lu, et al., 2006 |
Van Den Dool and Kratz RI, non-polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | DB-5 | 916.7 | Xu, van Stee, et al., 2003 | 30. m/0.25 mm/1. μm, He, 2.5 K/min; Tstart: 50. C; Tend: 200. C |
Normal alkane RI, non-polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | HP-5 | 930. | Splivallo, Bossi, et al., 2007 | He; Program: 50C => 3C/min => 200C(10min) => 10C/min => 290C(10min) |
Capillary | Methyl Silicone | 900. | Estrada and Gutierrez, 1999 | Program: not specified |
Capillary | OV-1, SE-30, Methyl silicone, SP-2100, OV-101, DB-1, etc. | 955. | Waggott and Davies, 1984 | Hydrogen; Column length: 50. m; Column diameter: 0.32 mm; Program: not specified |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, Mass spectrum (electron ionization), UV/Visible spectrum, Gas Chromatography, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Seller, 1970
Seller, P.,
Enthalpies of formation of some aliphatic branched ketones,
J. Chem. Thermodyn., 1970, 2, 211-219. [all data]
Howard, Mears, et al., 1947
Howard, F.L.; Mears, T.W.; Fookson, A.; Pomerantz, P.; Brooks, D.B.,
Preparation and physical properties of several aliphatic hydrocarbons and intermediates,
J. Res. Natl. Bur. Stand. (U. S.), 1947, 38, 365. [all data]
Peacock and Fuchs, 1977
Peacock, L. Alan; Fuchs, Richard,
Enthalpy of vaporization measurements by gas chromatography,
J. Am. Chem. Soc., 1977, 99, 16, 5524-5525, https://doi.org/10.1021/ja00458a070
. [all data]
Wadsö, Murto, et al., 1966
Wadsö, Ingemar; Murto, Maija-Leena; Bergson, Göran; Ehrenberg, L.; Brunvoll, J.; Bunnenberg, E.; Djerassi, Carl; Records, Ruth,
Heats of Vaporization for a Number of Organic Compounds at 25 degrees C.,
Acta Chem. Scand., 1966, 20, 544-552, https://doi.org/10.3891/acta.chem.scand.20-0544
. [all data]
Wadso, 1966
Wadso, I.,
Acta Chem. Scand., 1966, 20, 544. [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]
Hernandez, Masclet, et al., 1977
Hernandez, R.; Masclet, P.; Mouvier, G.,
Spectroscopie de photoelectrons d'aldehydes et de cetones aliphatiques,
J. Electron Spectrosc. Relat. Phenom., 1977, 10, 333. [all data]
Mouvier and Hernandez, 1975
Mouvier, G.; Hernandez, R.,
Ionisation and appearance potentials of alkylketones,
Org. Mass Spectrom., 1975, 10, 958. [all data]
Cocksey, Eland, et al., 1971
Cocksey, B.J.; Eland, J.H.D.; Danby, C.J.,
The effect of alkyl substitution on ionisation potential,
J. Chem. Soc., 1971, (B), 790. [all data]
Vilesov, 1960
Vilesov, F.I.,
The photoionization of vapors of compounds whose molecules contain carbonyl groups,
Dokl. Phys. Chem., 1960, 132, 521, In original 1332. [all data]
Hayes, 1966
Hayes, W.P.,
UV atlas of organic compounds, 1966, 1, B1/2. [all data]
Hu, Lu, et al., 2006
Hu, X.-F.; Lu, C.-H.; Yin, C.-S.,
Modeling Gas Chromatographic Retention Indices of Oxygen-containing Compounds by Novel Atom-type Topological Indices,
Chinese Journal of Chemical Physics, 2006, 19, 3, 243-247, https://doi.org/10.1360/cjcp2006.19(3).243.5
. [all data]
Xu, van Stee, et al., 2003
Xu, X.; van Stee, L.L.P.; Williams, J.; Beens, J.; Adahchour, M.; Vreuls, R.J.J.; Brinkman, U.A.Th.; Lelieveld, J.,
Comprehensive two-dimensional gas chromatography (GC×GC) measurements of volatile organic compounds in the atmosphere,
Atmos. Chem. Phys., 2003, 3, 3, 665-682, https://doi.org/10.5194/acp-3-665-2003
. [all data]
Splivallo, Bossi, et al., 2007
Splivallo, R.; Bossi, S.; Maffei, M.; Bonfante, P.,
Discrimination of truffle fruiting body versus mycelial aromas by stir bar sorptive extraction,
Phytochemistry, 2007, 68, 20, 2584-2598, https://doi.org/10.1016/j.phytochem.2007.03.030
. [all data]
Estrada and Gutierrez, 1999
Estrada, E.; Gutierrez, Y.,
Modeling chromatographic parameters by a novel graph theoretical sub-structural approach,
J. Chromatogr. A, 1999, 858, 2, 187-199, https://doi.org/10.1016/S0021-9673(99)00808-0
. [all data]
Waggott and Davies, 1984
Waggott, A.; Davies, I.W.,
Identification of organic pollutants using linear temperature programmed retention indices (LTPRIs) - Part II, 1984, retrieved from http://dwi.defra.gov.uk/research/completed-research/reports/dwi0383.pdf. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, Mass spectrum (electron ionization), UV/Visible spectrum, Gas Chromatography, References
- Symbols used in this document:
AE Appearance energy Tboil Boiling point Tfus Fusion (melting) point ΔcH°liquid Enthalpy of combustion of liquid at standard conditions ΔfH°gas Enthalpy of formation of gas at standard conditions ΔfH°liquid Enthalpy of formation of liquid at standard conditions ΔvapH° Enthalpy of vaporization at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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