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2-Butanone, 3,3-dimethyl-

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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
Deltafgas-69.47 ± 0.21kcal/molCcbHarrop, Head, et al., 1970ht. 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 ± 0.065385.67von Geiseler G., 1973GT
43.970 ± 0.067392.13
44.450 ± 0.067399.53
44.840 ± 0.067405.07
45.210 ± 0.067410.70

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 as indicated in comments:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DH - Eugene S. Domalski and Elizabeth D. Hearing

Quantity Value Units Method Reference Comment
Deltafliquid-78.523 ± 0.067kcal/molCcbHarrop, Head, et al., 1970ht. of vaporization was from a private communication; ALS
Quantity Value Units Method Reference Comment
Deltacliquid-895.67 ± 0.19kcal/molCcbHarrop, Head, et al., 1970ht. of vaporization was from a private communication; Corresponding «DELTA»fliquid = -78.525 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS
Quantity Value Units Method Reference Comment
liquid67.50cal/mol*KN/AAndon, Counsell, et al., 1970DH

Constant pressure heat capacity of liquid

Cp,liquid (cal/mol*K) Temperature (K) Reference Comment
49.45298.15Andon, Counsell, et al., 1970T = 10 to 360 K.; DH
49.55298.15Harrop, Head, et al., 1970DH

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
DH - Eugene S. Domalski and Elizabeth D. Hearing
CAL - James S. Chickos, William E. Acree, Jr., Joel F. Liebman, Students of Chem 202 (Introduction to the Literature of Chemistry), University of Missouri -- St. Louis

Quantity Value Units Method Reference Comment
Tboil379. ± 1.KAVGN/AAverage of 33 out of 38 values; Individual data points
Quantity Value Units Method Reference Comment
Tfus220.65KN/AVorontsova and Vlasov, 1987Crystal phase 1 phase; Uncertainty assigned by TRC = 0.5 K; TRC
Tfus223.4KN/AHill and Kropa, 1933Uncertainty assigned by TRC = 2. K; TRC
Tfus220.65KN/ATimmermans and Mattaar, 1921Uncertainty assigned by TRC = 0.5 K; TRC
Quantity Value Units Method Reference Comment
Ttriple221.74KN/AAndon, Counsell, et al., 1970, 2Uncertainty assigned by TRC = 0.05 K; TRC
Quantity Value Units Method Reference Comment
Tc562.9KN/AMajer and Svoboda, 1985 
Quantity Value Units Method Reference Comment
Deltavap9.1kcal/molN/AMajer and Svoboda, 1985 
Deltavap9.15kcal/molN/AAmbrose, Ellender, et al., 1975AC
Deltavap9.05 ± 0.02kcal/molVHarrop, Head, et al., 1970ht. of vaporization was from a private communication; ALS
Deltavap9.06 ± 0.02kcal/molCHarrop, Head, et al., 1970AC

Enthalpy of vaporization

DeltavapH (kcal/mol) Temperature (K) Method Reference Comment
12.137441.4N/ASvoboda, Kubes, et al., 1992Value corrected to 298.15 K.; DH
7.980379.3N/AMajer and Svoboda, 1985 
9.03 ± 0.02308.CSvoboda, Kubes, et al., 1992AC
8.96 ± 0.02313.CSvoboda, Kubes, et al., 1992AC
8.82 ± 0.02323.CSvoboda, Kubes, et al., 1992AC
8.77 ± 0.02328.CSvoboda, Kubes, et al., 1992AC
8.56 ± 0.02338.CSvoboda, Kubes, et al., 1992AC
8.46 ± 0.02343.CSvoboda, Kubes, et al., 1992AC
8.37 ± 0.02348.CSvoboda, Kubes, et al., 1992AC
8.82326.AStephenson and Malanowski, 1987Based on data from 311. - 381. K.; AC
8.34378.AStephenson and Malanowski, 1987Based on data from 363. - 400. K.; AC
8.08411.AStephenson and Malanowski, 1987Based on data from 396. - 509. K.; AC
7.91506.AStephenson and Malanowski, 1987Based on data from 491. - 567. K.; AC
9.15304.AStephenson and Malanowski, 1987Based on data from 289. - 402. K. See also Ambrose, Ellender, et al., 1975.; AC
8.63338.CGeiseler, Quitzsch, et al., 1973AC

Enthalpy of vaporization

ΔvapH = A exp(-βTr) (1 − Tr)β
    ΔvapH = Enthalpy of vaporization (at saturation pressure) (kcal/mol)
    Tr = reduced temperature (T / Tc)

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Temperature (K) A (kcal/mol) beta Tc (K) Reference Comment
298. - 378.12.50.2491562.9Majer and Svoboda, 1985 

Enthalpy of fusion

DeltafusH (kcal/mol) Temperature (K) Reference Comment
2.7079221.74Andon, Counsell, et al., 1970DH
2.710221.7Domalski and Hearing, 1996AC

Entropy of fusion

DeltafusS (cal/mol*K) Temperature (K) Reference Comment
12.21221.74Andon, Counsell, et al., 1970DH
12.20221.7Domalski and Hearing, 1996CAL

In addition to the Thermodynamics Research Center (TRC) data available from this site, much more physical and chemical property data is available from the following TRC products:


Reaction 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:
B - John E. Bartmess
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Note: Please consider using the reaction search for this species. This page allows searching of all reactions involving this species. A general reaction search form is also available. Future versions of this site may rely on reaction search pages in place of the enumerated reaction displays seen below.

Individual Reactions

C6H11O- + Hydrogen cation = 2-Butanone, 3,3-dimethyl-

By formula: C6H11O- + H+ = C6H12O

Quantity Value Units Method Reference Comment
Deltar369.1 ± 2.3kcal/molD-EABrinkman, Berger, et al., 1993gas phase; B
Quantity Value Units Method Reference Comment
Deltar362.4 ± 2.5kcal/molH-TSBrinkman, Berger, et al., 1993gas phase; B

2,2-Dimethoxy-3,3-dimethyl-butane + Water = 2Methyl Alcohol + 2-Butanone, 3,3-dimethyl-

By formula: C8H18O2 + H2O = 2CH4O + C6H12O

Quantity Value Units Method Reference Comment
Deltar0.819 ± 0.013kcal/molCmWiberg and Squires, 1979liquid phase; Heat of hydrolysis; 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
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 ± 0.03eVN/AN/AL
Quantity Value Units Method Reference Comment
Proton affinity (review)200.8kcal/molN/AHunter and Lias, 1998HL
Quantity Value Units Method Reference Comment
Gas basicity193.2kcal/molN/AHunter and Lias, 1998HL

Gas basicity at 298K

Gas basicity (review) (kcal/mol) Reference Comment
193.6 ± 0.1Decouzon, Gal, et al., 1996T = 338K; MM
193.5Decouzon, Gal, et al., 1996T = T(eff) = 430K; MM

Ionization energy determinations

IE (eV) Method Reference Comment
9.4EIDommrose and Grutzmacher, 1987LBLHLM
9.117 ± 0.005PEHernandez, Masclet, et al., 1977LLK
9.17 ± 0.06EIMouvier and Hernandez, 1975LLK
9.11 ± 0.01PEMouvier and Hernandez, 1975LLK
9.24PEBrown, 1975LLK
8.88 ± 0.04PEMiller, Koch, et al., 1973LLK
9.14 ± 0.01PECocksey, Eland, et al., 1971LLK
9.17 ± 0.03PIWatanabe, Nakayama, et al., 1962RDSH
9.18 ± 0.03PIVilesov, 1960RDSH
9.21PETam, Yee, et al., 1974Vertical value; LLK

Appearance energy determinations

Ion AE (eV) Other Products MethodReferenceComment
C2H3O+~11.3?EIMouvier and Hernandez, 1975LLK
C4H9+10.02 ± 0.05CH3COEIHolmes and Lossing, 1984LBLHLM

De-protonation reactions

C6H11O- + Hydrogen cation = 2-Butanone, 3,3-dimethyl-

By formula: C6H11O- + H+ = C6H12O

Quantity Value Units Method Reference Comment
Deltar369.1 ± 2.3kcal/molD-EABrinkman, Berger, et al., 1993gas phase; B
Quantity Value Units Method Reference Comment
Deltar362.4 ± 2.5kcal/molH-TSBrinkman, Berger, et al., 1993gas phase; B

IR 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.

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

Gas Phase Spectrum

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IR 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

This IR spectrum is from the NIST/EPA Gas-Phase Infrared Database .


Mass spectrum (electron ionization)

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, UV/Visible 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 by: NIST Mass Spectrometry Data Center, William E. Wallace, director

Spectrum

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Mass spectrum
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Additional Data

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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 Japan AIST/NIMC Database- Spectrum MS-NW- 893
NIST MS number 228726

All mass spectra in this site (plus many more) are available from the NIST/EPA/NIH Mass Spectral Library. Please see the following for information about the library and its accompanying search program.


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.

Data compiled by: Victor Talrose, Alexander N. Yermakov, Alexy A. Usov, Antonina A. Goncharova, Axlexander N. Leskin, Natalia A. Messineva, Natalia V. Trusova, Margarita V. Efimkina

Spectrum

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UVVis spectrum
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Additional Data

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Source Uno, et al., 1988
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. 17357
Instrument Hitachi 323
Boiling point 106

References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible 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]

Andon, Counsell, et al., 1970
Andon, R.J.L.; Counsell, J.F.; Lees, E.B.; Martin, J.F., Thermodynamic properties of organic oxygen compounds. Part XXIII. Low-temperature heat capacity and entropy of C6, C7, and C9 ketones, 1970, J. [all data]

Vorontsova and Vlasov, 1987
Vorontsova, N.A.; Vlasov, O.N., Determination of saturated vapor pressure of Bayletone and its semiproducts, Deposited Doc. ONIITEkhim Cherkassy, 1987, Doc. No. 1423 khp - 87, 1987. [all data]

Hill and Kropa, 1933
Hill, G.A.; Kropa, E.L., Some Halogented Pinacalones, J. Am. Chem. Soc., 1933, 55, 2509. [all data]

Timmermans and Mattaar, 1921
Timmermans, J.; Mattaar, J.F., Freezing points of orgainic substances VI. New experimental determinations., Bull. Soc. Chim. Belg., 1921, 30, 213. [all data]

Andon, Counsell, et al., 1970, 2
Andon, R.J.L.; Counsell, J.F.; Lees, E.B.; Martin, J.F., Thermodynamic Properties of Organic Oxygen Compounds Part XXIII. Low- temperature Heat Capacity and Entropy of C6, C7, and C9 Ketones, J. Chem. Soc. A, 1970, 1970, 833. [all data]

Majer and Svoboda, 1985
Majer, V.; Svoboda, V., Enthalpies of Vaporization of Organic Compounds: A Critical Review and Data Compilation, Blackwell Scientific Publications, Oxford, 1985, 300. [all data]

Ambrose, Ellender, et al., 1975
Ambrose, D.; Ellender, J.H.; Lees, E.B.; Sprake, C.H.S.; Townsend, R., Thermodynamic properties of organic oxygen compounds XXXVIII. Vapour pressures of some aliphatic ketones, The Journal of Chemical Thermodynamics, 1975, 7, 5, 453-472, https://doi.org/10.1016/0021-9614(75)90275-X . [all data]

Svoboda, Kubes, et al., 1992
Svoboda, V.; Kubes, V.; Basarova, P., Enthalpies of vaporization and cohesive energies of hexan-2-one, 2-methylpentan-4-one, 2,2-dimethylbutan-3-one, 2,6-dimethylheptan-4-one and cyclohexanone, J. Chem. Thermodynam., 1992, 24, 333-336. [all data]

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]

Geiseler, Quitzsch, et al., 1973
Geiseler, G.; Quitzsch, K.; Hofmann, H.-P.; Pfestorf, R.Z., Z. Phys. Chem. (Leipzig), 1973, 252, 170. [all data]

Domalski and Hearing, 1996
Domalski, Eugene S.; Hearing, Elizabeth D., Heat Capacities and Entropies of Organic Compounds in the Condensed Phase. Volume III, J. Phys. Chem. Ref. Data, 1996, 25, 1, 1, https://doi.org/10.1063/1.555985 . [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]

Wiberg and Squires, 1979
Wiberg, K.B.; Squires, R.R., Thermodynamics of hydrolysis aliphatic ketals. An entropy component of steric effects, J. Am. Chem. Soc., 1979, 101, 5512-5515. [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]

Uno, et al., 1988
Uno, B., et al., Bull. Chem. Soc. Japan, 1988, 61, 1431. [all data]


Notes

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, References