2-Butanone, 3,3-dimethyl-
- Formula: C6H12O
- Molecular weight: 100.1589
- IUPAC Standard InChIKey: PJGSXYOJTGTZAV-UHFFFAOYSA-N
- CAS Registry Number: 75-97-8
- 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: tert-Butyl methyl ketone; Methyl tert-butyl ketone; Pinacolin; Pinacoline; Pinacolone; 2,2-Dimethyl-3-butanone; 2,2-Dimethylbutanone; 3,3-Dimethyl-2-butanone; 3,3-Dimethylbutanone; tert-C4H9COCH3; Ketone, tert-butyl methyl; 1,1,1-Trimethylacetone; t-Butyl methyl ketone; Ketone, t-butyl methyl; Methyl t-butyl ketone; Pinakolin; 1,1-Dimethylethyl methyl ketone; 3,3-Dimethyl-butan-2-one; NSC 935
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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 as indicated in comments:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
GT - Glushko Thermocenter, Russian Academy of Sciences, Moscow
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°gas | -69.47 ± 0.21 | kcal/mol | Ccb | Harrop, Head, et al., 1970 | ht. of vaporization was from a private communication; ALS |
Constant pressure heat capacity of gas
Cp,gas (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
43.499 ± 0.065 | 385.67 | von Geiseler G., 1973 | GT |
43.970 ± 0.067 | 392.13 | ||
44.450 ± 0.067 | 399.53 | ||
44.840 ± 0.067 | 405.07 | ||
45.210 ± 0.067 | 410.70 |
Gas phase ion energetics data
Go To: Top, Gas phase thermochemistry 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 evaluated as indicated in comments:
HL - Edward P. Hunter and Sharon G. Lias
L - Sharon G. Lias
Data compiled as indicated in comments:
B - John E. Bartmess
MM - Michael M. Meot-Ner (Mautner)
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
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
IE (evaluated) | 9.14 ± 0.03 | eV | N/A | N/A | L |
Quantity | Value | Units | Method | Reference | Comment |
Proton affinity (review) | 200.8 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
Quantity | Value | Units | Method | Reference | Comment |
Gas basicity | 193.2 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
Gas basicity at 298K
Gas basicity (review) (kcal/mol) | Reference | Comment |
---|---|---|
193.6 ± 0.1 | Decouzon, Gal, et al., 1996 | T = 338K; MM |
193.5 | Decouzon, Gal, et al., 1996 | T = T(eff) = 430K; MM |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
9.4 | EI | Dommrose and Grutzmacher, 1987 | LBLHLM |
9.117 ± 0.005 | PE | Hernandez, Masclet, et al., 1977 | LLK |
9.17 ± 0.06 | EI | Mouvier and Hernandez, 1975 | LLK |
9.11 ± 0.01 | PE | Mouvier and Hernandez, 1975 | LLK |
9.24 | PE | Brown, 1975 | LLK |
8.88 ± 0.04 | PE | Miller, Koch, et al., 1973 | LLK |
9.14 ± 0.01 | PE | Cocksey, Eland, et al., 1971 | LLK |
9.17 ± 0.03 | PI | Watanabe, Nakayama, et al., 1962 | RDSH |
9.18 ± 0.03 | PI | Vilesov, 1960 | RDSH |
9.21 | PE | Tam, Yee, et al., 1974 | Vertical value; LLK |
Appearance energy determinations
Ion | AE (eV) | Other Products | Method | Reference | Comment |
---|---|---|---|---|---|
C2H3O+ | ~11.3 | ? | EI | Mouvier and Hernandez, 1975 | LLK |
C4H9+ | 10.02 ± 0.05 | CH3CO | EI | Holmes and Lossing, 1984 | LBLHLM |
De-protonation reactions
C6H11O- + =
By formula: C6H11O- + H+ = C6H12O
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 369.1 ± 2.3 | kcal/mol | D-EA | Brinkman, Berger, et al., 1993 | gas phase; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 362.4 ± 2.5 | kcal/mol | H-TS | Brinkman, Berger, et al., 1993 | gas phase; B |
IR Spectrum
Go To: Top, Gas phase thermochemistry 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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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 | Sadtler Research Labs Under US-EPA Contract |
State | gas |
References
Go To: Top, Gas phase thermochemistry 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.
Harrop, Head, et al., 1970
Harrop, D.; Head, A.J.; Lewis, G.B.,
Thermodynamic properties of organic oxygen compounds. 22. Enthalpies of combustion of some aliphatic ketones,
J. Chem. Thermodyn., 1970, 2, 203-210. [all data]
von Geiseler G., 1973
von Geiseler G.,
The heat capacity and the heat of vaporization of isomeric butylmethylketones and propylacetates,
Z. Phys. Chem. (Leipzig), 1973, 252, 170-176. [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]
Decouzon, Gal, et al., 1996
Decouzon, M.; Gal, J.E.; Herreros, M.; Marai, P.C.; Murrell, J.; Todd, J.F.J.,
On the Use of the Kinetic Method for the Determination of Proton Affinities by Fourier-Transfrom Ion Cyclotron Resonance Mass Spectrometry,
Rapid. Comm. Mass Spectrom., 1996, 10, 242. [all data]
Dommrose and Grutzmacher, 1987
Dommrose, A.; Grutzmacher, H.,
Destablized carbenium ions: A-acetyl-a,a-dimethylmethyl cations,
Int. J. Mass Spectrom. Ion Processes, 1987, 76, 95. [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]
Brown, 1975
Brown, R.S.,
A photoelectron investigation of acyl silanes: The photoelectron spectra of trimethylsilyl phenyl ketone and phenyl tert-butyl ketone,
Can. J. Chem., 1975, 53, 2446. [all data]
Miller, Koch, et al., 1973
Miller, L.L.; Koch, V.R.; Koenig, T.; Tuttle, M.,
Photoelectron spectroscopy and the anodic fragmentation of adamantane derivatives,
J. Am. Chem. Soc., 1973, 95, 5075. [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]
Watanabe, Nakayama, et al., 1962
Watanabe, K.; Nakayama, T.; Mottl, J.,
Ionization potentials of some molecules,
J. Quant. Spectry. Radiative Transfer, 1962, 2, 369. [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]
Tam, Yee, et al., 1974
Tam, W.-C.; Yee, D.; Brion, C.E.,
Photoelectron spectra of some aldehydes and ketones,
J. Electron Spectrosc. Relat. Phenom., 1974, 4, 77. [all data]
Holmes and Lossing, 1984
Holmes, J.L.; Lossing, F.P.,
Heats of formation of organic radicals from appearance energies,
Int. J. Mass Spectrom. Ion Processes, 1984, 58, 113. [all data]
Brinkman, Berger, et al., 1993
Brinkman, E.A.; Berger, S.; Marks, J.; Brauman, J.I.,
Molecular Rotation and the Observation of Dipole-Bound States of Anions,
J. Chem. Phys., 1993, 99, 10, 7586, https://doi.org/10.1063/1.465688
. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Gas phase ion energetics data, IR Spectrum, References
- Symbols used in this document:
AE Appearance energy Cp,gas Constant pressure heat capacity of gas IE (evaluated) Recommended ionization energy ΔfH°gas Enthalpy of formation of gas at standard conditions ΔrG° Free energy of reaction at standard conditions ΔrH° Enthalpy of reaction at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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