2-Butanone, 3-methyl-

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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
Δfgas-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

Phase change data

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 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., 1968Uncertainty 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
ρc3.23mol/lN/AKobe, Crawford, et al., 1955Uncertainty assigned by TRC = 0.29 mol/l; TRC
Quantity Value Units Method Reference Comment
Δvap8.812kcal/molN/AMajer and Svoboda, 1985 
Δvap8.798kcal/molVUchytilova, Majer, et al., 1983ALS
Δvap8.80kcal/molCUchytilova, Majer, et al., 1983AC
Δvap8.82kcal/molN/AAmbrose, Ellender, et al., 1975AC

Enthalpy of vaporization

ΔvapH (kcal/mol) Temperature (K) Method Reference Comment
7.732367.4N/AMajer and Svoboda, 1985 
8.48326.AStephenson and Malanowski, 1987Based on data from 311. to 369. K.; AC
8.08378.AStephenson and Malanowski, 1987Based on data from 363. to 415. K.; AC
7.79420.AStephenson and Malanowski, 1987Based on data from 405. to 500. K.; AC
8.37343.AStephenson and Malanowski, 1987Based on data from 328. to 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) β Tc (K) Reference Comment
298. to 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 to 362.15.619881806.925-40.618Stull, 1947Coefficents calculated by NIST from author's data.

Enthalpy of fusion

ΔfusH (kcal/mol) Temperature (K) Reference Comment
2.233180.01Andon, Counsell, et al., 1968, 2DH
2.23180.Domalski and Hearing, 1996AC

Entropy of fusion

ΔfusS (cal/mol*K) Temperature (K) Reference Comment
12.40180.01Andon, Counsell, et al., 1968, 2DH

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:


Gas phase ion energetics data

Go To: Top, Gas phase thermochemistry data, Phase change data, 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
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron

View reactions leading to C5H10O+ (ion structure unspecified)

Quantity Value Units Method Reference Comment
IE (evaluated)9.31 ± 0.02eVN/AN/AL
Quantity Value Units Method Reference Comment
Proton affinity (review)199.9kcal/molN/AHunter and Lias, 1998HL
Quantity Value Units Method Reference Comment
Gas basicity192.3kcal/molN/AHunter and Lias, 1998HL

Ionization energy determinations

IE (eV) Method Reference Comment
9.298 ± 0.005PEHernandez, Masclet, et al., 1977LLK
9.30 ± 0.01PEMouvier and Hernandez, 1975LLK
9.30 ± 0.04EIMouvier and Hernandez, 1975LLK
9.36PETam, Yee, et al., 1974LLK
9.30 ± 0.01PECocksey, Eland, et al., 1971LLK
9.30 ± 0.02PIMurad and Inghram, 1964RDSH
9.32 ± 0.02PIWatanabe, Nakayama, et al., 1962RDSH

Appearance energy determinations

Ion AE (eV) Other Products MethodReferenceComment
C2H3O+10.68?EIMouvier and Hernandez, 1975LLK
C2H3O+10.4iso-C3H7PIMurad and Inghram, 1964RDSH
C4H7O+9.9?EIMouvier and Hernandez, 1975LLK
C4H7O+9.94CH3PIMurad and Inghram, 1964RDSH

De-protonation reactions

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

By formula: C5H9O- + H+ = C5H10O

Quantity Value Units Method Reference Comment
Δr369.3 ± 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
Δr362.8 ± 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
Δr367.3 ± 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
Δr360.5 ± 2.0kcal/molIMRECumming and Kebarle, 1978gas phase; Structure assignment revised to less-substituted site: Chyall, Brickhouse, et al., 1994; B

References

Go To: Top, Gas phase thermochemistry data, Phase change data, Gas phase ion energetics data, 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]

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
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]

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, 1894-1897. [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]

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]

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]

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]

Murad and Inghram, 1964
Murad, E.; Inghram, M.G., Photoionization of aliphatic ketones, J. Chem. Phys., 1964, 40, 3263. [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]

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]


Notes

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