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2-Butanone, 3-methyl-

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Gas phase thermochemistry data

Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, IR Spectrum, Mass spectrum (electron ionization), References, Notes

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-62.76 ± 0.21kcal/molCcbHarrop, Head, et al., 1970ALS

Constant pressure heat capacity of gas

Cp,gas (cal/mol*K) Temperature (K) Reference Comment
33.360358.15Hales J.L., 1967GT
35.091383.15
36.869408.15
38.540433.15
39.859453.15
41.130473.15

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-71.58 ± 0.21kcal/molCcbHarrop, Head, et al., 1970ALS
Quantity Value Units Method Reference Comment
Deltacliquid-740.3 ± 0.2kcal/molCcbHarrop, Head, et al., 1970Corresponding «DELTA»fliquid = -71.575 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS
Quantity Value Units Method Reference Comment
liquid64.17cal/mol*KN/AAndon, Counsell, et al., 1968DH

Constant pressure heat capacity of liquid

Cp,liquid (cal/mol*K) Temperature (K) Reference Comment
43.02298.15Harrop, Head, et al., 1970DH
43.00298.15Andon, Counsell, et al., 1968T = 10 to 320 K.; DH

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
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
AC - William E. Acree, Jr., James S. Chickos
DH - Eugene S. Domalski and Elizabeth D. Hearing

Quantity Value Units Method Reference Comment
Tboil367. ± 2.KAVGN/AAverage of 40 out of 41 values; Individual data points
Quantity Value Units Method Reference Comment
Tfus178.75KN/AMears, Fookson, et al., 1950Uncertainty assigned by TRC = 0.4 K; TRC
Tfus181.15KN/ATimmermans and Mattaar, 1921Uncertainty assigned by TRC = 0.6 K; TRC
Quantity Value Units Method Reference Comment
Ttriple180.01KN/AAndon, Counsell, et al., 1968, 2Uncertainty assigned by TRC = 0.06 K; TRC
Quantity Value Units Method Reference Comment
Tc553.1KN/AQuadri and Kudchadker, 1991Uncertainty assigned by TRC = 0.4 K; TRC
Tc553.4KN/AMajer and Svoboda, 1985 
Tc553.4KN/AKobe, Crawford, et al., 1955Uncertainty assigned by TRC = 0.83 K; TRC
Quantity Value Units Method Reference Comment
Pc37.50atmN/AQuadri and Kudchadker, 1991Uncertainty assigned by TRC = 0.20 atm; TRC
Pc38.00atmN/AKobe, Crawford, et al., 1955Uncertainty assigned by TRC = 0.477 atm; TRC
Quantity Value Units Method Reference Comment
rhoc3.23mol/lN/AKobe, Crawford, et al., 1955Uncertainty assigned by TRC = 0.29 mol/l; TRC
Quantity Value Units Method Reference Comment
Deltavap8.812kcal/molN/AMajer and Svoboda, 1985 
Deltavap8.798kcal/molVUchytilova, Majer, et al., 1983ALS
Deltavap8.80kcal/molCUchytilova, Majer, et al., 1983AC
Deltavap8.82kcal/molN/AAmbrose, Ellender, et al., 1975AC

Enthalpy of vaporization

DeltavapH (kcal/mol) Temperature (K) Method Reference Comment
7.732367.4N/AMajer and Svoboda, 1985 
8.48326.AStephenson and Malanowski, 1987Based on data from 311. - 369. K.; AC
8.08378.AStephenson and Malanowski, 1987Based on data from 363. - 415. K.; AC
7.79420.AStephenson and Malanowski, 1987Based on data from 405. - 500. K.; AC
8.37343.AStephenson and Malanowski, 1987Based on data from 328. - 377. K. See also Ambrose, Ellender, et al., 1975.; AC
8.37 ± 0.02327.CHales, Lees, et al., 1967AC
8.08 ± 0.02346.CHales, Lees, et al., 1967AC
7.72 ± 0.02367.CHales, Lees, et al., 1967AC

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. - 368.12.880.2911553.4Majer and Svoboda, 1985 

Antoine Equation Parameters

log10(P) = A − (B / (T + C))
    P = vapor pressure (atm)
    T = temperature (K)

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Temperature (K) A B C Reference Comment
253.3 - 362.15.619881806.925-40.618Stull, 1947Coefficents calculated by NIST from author's data.

Enthalpy of fusion

DeltafusH (kcal/mol) Temperature (K) Reference Comment
2.233180.01Andon, Counsell, et al., 1968DH
2.23180.Domalski and Hearing, 1996AC

Entropy of fusion

DeltafusS (cal/mol*K) Temperature (K) Reference Comment
12.40180.01Andon, Counsell, et al., 1968DH

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

C5H9O- + Hydrogen cation = 2-Butanone, 3-methyl-

By formula: C5H9O- + H+ = C5H10O

Quantity Value Units Method Reference Comment
Deltar369.3 ± 2.7kcal/molG+TSChyall, Brickhouse, et al., 1994gas phase; By equilibration, more substituted site is less acidic than Me by 2.3 kcal/mol; B
Quantity Value Units Method Reference Comment
Deltar362.8 ± 2.5kcal/molIMREChyall, Brickhouse, et al., 1994gas phase; By equilibration, more substituted site is less acidic than Me by 2.3 kcal/mol; B

C5H9O- + Hydrogen cation = 2-Butanone, 3-methyl-

By formula: C5H9O- + H+ = C5H10O

Quantity Value Units Method Reference Comment
Deltar367.3 ± 2.2kcal/molG+TSCumming and Kebarle, 1978gas phase; Structure assignment revised to less-substituted site: Chyall, Brickhouse, et al., 1994; B
Quantity Value Units Method Reference Comment
Deltar360.5 ± 2.0kcal/molIMRECumming and Kebarle, 1978gas phase; Structure assignment revised to less-substituted site: Chyall, Brickhouse, et al., 1994; B

(CAS Reg. No. 60375-60-2 bullet 42949672952-Butanone, 3-methyl-) + 2-Butanone, 3-methyl- = CAS Reg. No. 60375-60-2

By formula: (CAS Reg. No. 60375-60-2 bullet 4294967295C5H10O) + C5H10O = CAS Reg. No. 60375-60-2

Quantity Value Units Method Reference Comment
Deltar40.3 ± 2.1kcal/molN/AHaas and Harrison, 1993gas phase; Both metastable and 50 eV collision energy.; B
Deltar40.2 ± 2.9kcal/molTherBoand, Houriet, et al., 1983gas phase; value altered from reference due to change in acidity scale; B

2,2-Dimethoxy-3-methylbutane + Water = 2-Butanone, 3-methyl- + 2Methyl Alcohol

By formula: C7H16O2 + H2O = C5H10O + 2CH4O

Quantity Value Units Method Reference Comment
Deltar4.86 ± 0.01kcal/molCmWiberg and Squires, 1979liquid phase; Heat of hydrolysis; ALS

2-Butanol, 3-methyl- = Hydrogen + 2-Butanone, 3-methyl-

By formula: C5H12O = H2 + C5H10O

Quantity Value Units Method Reference Comment
Deltar12.9 ± 0.38kcal/molEqkConnett, 1970gas phase; ALS

IR Spectrum

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Mass spectrum (electron ionization), 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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IR spectrum
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Notice: Concentration information is not available for this spectrum and, therefore, molar absorptivity values cannot be derived.

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

Spectrum

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Mass spectrum
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Additional Data

View image of digitized spectrum (can be printed in landscape orientation).

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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 D.HENNEBERG, MAX-PLANCK INSTITUTE, MULHEIM, WEST GERMANY
NIST MS number 61712

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.


References

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

Hales J.L., 1967
Hales J.L., Thermodynamic properties of organic oxygen compounds. Part 18. Vapor heat capacities and heats of vaporization of ethyl ketone, ethyl propyl ketone, methyl isopropyl ketone, and methyl phenyl ether, Trans. Faraday Soc., 1967, 63, 1876-1879. [all data]

Andon, Counsell, et al., 1968
Andon, R.J.L.; Counsell, J.F.; Martin, J.F., Thermodynamic properties of organic oxygen compounds. Part XX. The low-temperature heat capacity and entropy of C4 and C5 ketones, J. Chem. Soc. A, 1968, 1894-1897. [all data]

Mears, Fookson, et al., 1950
Mears, T.W.; Fookson, A.; Pomerantz, P.; Rich, E.H.; Dussinger, C.S.; Howard, F.L., Syntheses and Properties of Two Olefins, Six Paraffins, and Their Intermediates, J. Res. Natl. Bur. Stand. (U. S.), 1950, 44, 299. [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., 1968, 2
Andon, R.J.L.; Counsell, J.F.; Martin, J.F., Thermodynamic properties of organic oxygen compounds. Part XX. The low- temperature heat capacity and entropy of C4 and C5 ketones., J. Chem. Soc. A, 1968, 1968, 1894-7. [all data]

Quadri and Kudchadker, 1991
Quadri, S.K.; Kudchadker, A.P., Measurement of the critical temperatures and critical pressures of some thermally stable or mildly unstable esters, ketones, and ethers, J. Chem. Thermodyn., 1991, 23, 129-34. [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]

Kobe, Crawford, et al., 1955
Kobe, K.A.; Crawford, H.R.; Stephenson, R.W., Critical Properties and Vapor Pressures of Some Ketones, Ind. Eng. Chem., 1955, 47, 1767-72. [all data]

Uchytilova, Majer, et al., 1983
Uchytilova, V.; Majer, V.; Svoboda, V.; Hynek, V., Enthalpies of vaporization and cohesive enrgies for seven aliphatic ketones, J. Chem. Thermodyn., 1983, 15, 853-858. [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]

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]

Hales, Lees, et al., 1967
Hales, J.L.; Lees, E.B.; Ruxton, D.J., Thermodynamic properties of organic oxygen compounds. Part 18.-Vapour heat capacities and heats of vaporization of ethyl ketone, ethyl propyl ketone, methyl isopropyl ketone, and methyl phenyl ether, Trans. Faraday Soc., 1967, 63, 1876. [all data]

Stull, 1947
Stull, Daniel R., Vapor Pressure of Pure Substances. Organic and Inorganic Compounds, Ind. Eng. Chem., 1947, 39, 4, 517-540, https://doi.org/10.1021/ie50448a022 . [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]

Chyall, Brickhouse, et al., 1994
Chyall, L.J.; Brickhouse, M.D.; Schnute, M.E.; Squires, R.R., Kinetic versus thermodynamic control in the deprotonation of unsymmetrical ketones in the gas phase, J. Am. Chem. Soc., 1994, 116, 19, 8681, https://doi.org/10.1021/ja00098a031 . [all data]

Cumming and Kebarle, 1978
Cumming, J.B.; Kebarle, P., Summary of gas phase measurements involving acids AH. Entropy changes in proton transfer reactions involving negative ions. Bond dissociation energies D(A-H) and electron affinities EA(A), Can. J. Chem., 1978, 56, 1. [all data]

Haas and Harrison, 1993
Haas, M.J.; Harrison, A.G., The Fragmentation of Proton-Bound Cluster Ions and the Gas-Phase Acidities of Alcohols, Int. J. Mass Spectrom. Ion Proc., 1993, 124, 2, 115, https://doi.org/10.1016/0168-1176(93)80003-W . [all data]

Boand, Houriet, et al., 1983
Boand, G.; Houriet, R.; Baumann, T., The gas phase acidity of aliphatic alcohols, J. Am. Chem. Soc., 1983, 105, 2203. [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]

Connett, 1970
Connett, J.E., Chemical equilibria. Part III. Dehydrogenation of pentan-1-ol, pentan-2-ol, and 3-methylbutan-2-ol, J. Chem. Soc. A, 1970, 1284-1286. [all data]


Notes

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