Butanoic acid, 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 by: Donald R. Burgess, Jr.

Quantity Value Units Method Reference Comment
Δfgas-502.5 ± 6.6kJ/molN/AHancock, Watson, et al., 1954Value computed using ΔfHliquid° value of -561.6±5.9 kj/mol from Hancock, Watson, et al., 1954 and ΔvapH° value of 59.1±3 kj/mol from sec-alkanoic correlation.

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
Δfliquid-561.6 ± 5.9kJ/molCcbHancock, Watson, et al., 1954Reanalyzed by Cox and Pilcher, 1970, Original value = -561. kJ/mol; ALS
Quantity Value Units Method Reference Comment
Δcliquid-2835.1 ± 5.9kJ/molCcbHancock, Watson, et al., 1954Reanalyzed by Cox and Pilcher, 1970, Original value = -2840. kJ/mol; Corresponding Δfliquid = -561.62 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS

Constant pressure heat capacity of liquid

Cp,liquid (J/mol*K) Temperature (K) Reference Comment
197.1298.von Reis, 1881T = 290 to 470 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
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
Tboil448. ± 3.KAVGN/AAverage of 24 values; Individual data points
Quantity Value Units Method Reference Comment
Tfus243.85KN/ATimmermans, 1952Uncertainty assigned by TRC = 0.4 K; TRC
Tfus243.KN/ATimmermans, 1935Uncertainty assigned by TRC = 2. K; TRC
Tfus243.15KN/ATimmermans, 1934Uncertainty assigned by TRC = 0.4 K; TRC
Tfus235.15KN/ATimmermans, 1911Uncertainty assigned by TRC = 0.5 K; TRC
Quantity Value Units Method Reference Comment
Tc629.KN/AAmbrose and Ghiassee, 1987Uncertainty assigned by TRC = 1. K; TRC
Tc633.83KN/ABrown, 1906Uncertainty assigned by TRC = 6. K; TRC
Quantity Value Units Method Reference Comment
Pc34.00barN/AAmbrose and Ghiassee, 1987Uncertainty assigned by TRC = 0.25 bar; TRC
Quantity Value Units Method Reference Comment
Δvap61.2 ± 0.3kJ/molGSVerevkin, 2000Based on data from 293. to 323. K.; AC
Δvap57.5 ± 3.0kJ/molVKruif and Oonk, 1979ALS
Δvap58. ± 3.kJ/molTEKruif and Oonk, 1979Based on data from 243. to 259. K.; AC
Δvap46.91 ± 0.18kJ/molCKonicek and Wadso, 1970ALS

Enthalpy of vaporization

ΔvapH (kJ/mol) Temperature (K) Method Reference Comment
53.8411.N/AClifford, Ramjugernath, et al., 2004Based on data from 396. to 448. K.; AC
60.7 ± 0.3308.GSVerevkin, 2000Based on data from 293. to 323. K.; AC
55.8379.A,EBAmbrose and Ghiassee, 1987, 2Based on data from 364. to 464. K.; AC
56.6322.AStephenson and Malanowski, 1987Based on data from 307. to 448. K.; AC
45.9375.N/AKahlbaum, 1894Based on data from 360. to 377. K.; AC

Antoine Equation Parameters

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

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Temperature (K) A B C Reference Comment
359.8 to 377.3-0.2658550.172-320.762Kahlbaum, 1894, 2Coefficents calculated by NIST from author's data.

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 by: John E. Bartmess

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

C5H9O2- + Hydrogen cation = Butanoic acid, 3-methyl-

By formula: C5H9O2- + H+ = C5H10O2

Quantity Value Units Method Reference Comment
Δr1446. ± 8.8kJ/molG+TSCaldwell, Renneboog, et al., 1989gas phase
Δr1451. ± 8.8kJ/molG+TSTaft and Topsom, 1987gas phase
Quantity Value Units Method Reference Comment
Δr1416. ± 8.4kJ/molIMRECaldwell, Renneboog, et al., 1989gas phase
Δr1421. ± 8.4kJ/molIMRETaft and Topsom, 1987gas phase

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 compiled as indicated in comments:
B - John E. Bartmess
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
LBLHLM - Sharon G. Lias, John E. Bartmess, Joel F. Liebman, John L. Holmes, Rhoda D. Levin, and W. Gary Mallard

Ionization energy determinations

IE (eV) Method Reference Comment
10.51PEWatanabe, Yokoyama, et al., 1973Vertical value; LLK

Appearance energy determinations

Ion AE (eV) Other Products MethodReferenceComment
C2H4O2+10.8 ± 0.1C3H6EIAudier, Milliet, et al., 1985LBLHLM
C2H5O2+10.4 ± 0.1C3H5EIAudier, Milliet, et al., 1985LBLHLM

De-protonation reactions

C5H9O2- + Hydrogen cation = Butanoic acid, 3-methyl-

By formula: C5H9O2- + H+ = C5H10O2

Quantity Value Units Method Reference Comment
Δr1446. ± 8.8kJ/molG+TSCaldwell, Renneboog, et al., 1989gas phase; B
Δr1451. ± 8.8kJ/molG+TSTaft and Topsom, 1987gas phase; B
Quantity Value Units Method Reference Comment
Δr1416. ± 8.4kJ/molIMRECaldwell, Renneboog, et al., 1989gas phase; B
Δr1421. ± 8.4kJ/molIMRETaft and Topsom, 1987gas phase; B

References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry 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.

Hancock, Watson, et al., 1954
Hancock, C.K.; Watson, G.M.; Gilby, R.F., Heats of combustion of five-carbon fatty acids and their methyl and ethyl esters, J. Phys. Chem., 1954, 58, 127-129. [all data]

Cox and Pilcher, 1970
Cox, J.D.; Pilcher, G., Thermochemistry of Organic and Organometallic Compounds, Academic Press, New York, 1970, 1-636. [all data]

von Reis, 1881
von Reis, M.A., Die specifische Wärme flüssiger organischer Verbindungen und ihre Beziehung zu deren Moleculargewicht, Ann. Physik [3], 1881, 13, 447-464. [all data]

Timmermans, 1952
Timmermans, J., Freezing points of organic compounds. VVI New determinations., Bull. Soc. Chim. Belg., 1952, 61, 393. [all data]

Timmermans, 1935
Timmermans, J., Researches in Stoichiometry. I. The Heat of Fusion of Organic Compounds., Bull. Soc. Chim. Belg., 1935, 44, 17-40. [all data]

Timmermans, 1934
Timmermans, J., Theory of Concentrated Solutions XII., Bull. Soc. Chim. Belg., 1934, 43, 626. [all data]

Timmermans, 1911
Timmermans, J., Researches on the freezing point of organic liquid compounds, Bull. Soc. Chim. Belg., 1911, 25, 300. [all data]

Ambrose and Ghiassee, 1987
Ambrose, D.; Ghiassee, N.B., Vapor Pressures and Critical Temperatures and Critical Pressures of Some Alkanoic Acids: C1 to C10, J. Chem. Thermodyn., 1987, 19, 505. [all data]

Brown, 1906
Brown, J.C., The critical temperature and value of ml/theta of some carbon compounds, J. Chem. Soc., Trans., 1906, 89, 311. [all data]

Verevkin, 2000
Verevkin, S.P., Measurement and Prediction of the Monocarboxylic Acids Thermochemical Properties, J. Chem. Eng. Data, 2000, 45, 5, 953-960, https://doi.org/10.1021/je990282m . [all data]

Kruif and Oonk, 1979
Kruif, C.G.; Oonk, H.A.J., Enthalpies of vaporization and vapour pressures of seven aliphatic carboxylic acids, J. Chem. Thermodyn., 1979, 11, 287-290. [all data]

Konicek and Wadso, 1970
Konicek, J.; Wadso, I., Enthalpies of vaporization of organic compounds. VII. Some carboxylic acids, Acta Chem. Scand., 1970, 24, 2612-26. [all data]

Clifford, Ramjugernath, et al., 2004
Clifford, Scott L.; Ramjugernath, Deresh; Raal, J. David, Subatmospheric Vapor Pressure Curves for Propionic Acid, Butyric Acid, Isobutyric Acid, Valeric Acid, Isovaleric Acid, Hexanoic Acid, and Heptanoic Acid, J. Chem. Eng. Data, 2004, 49, 5, 1189-1192, https://doi.org/10.1021/je034180e . [all data]

Ambrose and Ghiassee, 1987, 2
Ambrose, D.; Ghiassee, N.B., Vapour pressures and critical temperatures and critical pressures of some alkanoic acids: C1 to C10, The Journal of Chemical Thermodynamics, 1987, 19, 5, 505-519, https://doi.org/10.1016/0021-9614(87)90147-9 . [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]

Kahlbaum, 1894
Kahlbaum, G.W.A., Z. Phys. Chem., Stoechiom. Verwandtschaftsl., 1894, 13, 14. [all data]

Kahlbaum, 1894, 2
Kahlbaum, G.W.A., Studien uber Dampfspannkraftsmessungen, Z. Phys. Chem. (Leipzig), 1894, 13, 14-55. [all data]

Caldwell, Renneboog, et al., 1989
Caldwell, G.; Renneboog, R.; Kebarle, P., Gas Phase Acidities of Aliphatic Carboxylic Acids, Based on Measurements of Proton Transfer Equilibria, Can. J. Chem., 1989, 67, 4, 661, https://doi.org/10.1139/v89-092 . [all data]

Taft and Topsom, 1987
Taft, R.W.; Topsom, R.D., The Nature and Analysis of Substituent Effects, Prog. Phys. Org. Chem., 1987, 16, 1. [all data]

Watanabe, Yokoyama, et al., 1973
Watanabe, I.; Yokoyama, Y.; Ikeda, S., Lone pair ionization potentials of carboxylic acids determined by He(I) photoelectron spectroscopy, Bull. Chem. Soc. Jpn., 1973, 46, 1959. [all data]

Audier, Milliet, et al., 1985
Audier, H.; Milliet, A.; Sozzi, G., Isomerisation des cation radicaux acides pentanoique et methyl-3-butanoique in phase gazeuse, Bull. Soc. Chim. France, 1985, 5, 833. [all data]


Notes

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