Methyl isobutyrate
- Formula: C5H10O2
- Molecular weight: 102.1317
- IUPAC Standard InChIKey: BHIWKHZACMWKOJ-UHFFFAOYSA-N
- CAS Registry Number: 547-63-7
- 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: Propanoic acid, 2-methyl-, methyl ester; Isobutyric acid, methyl ester; Methyl 2-methylpropanoate; Methyl 2-methylpropionate; (CH3)2CHC(O)OCH3; Methyl isobutanoate; Methylester kyseliny isomaselne; Methyl methylpropanoate; NSC 126780
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Phase change data
Go To: Top, Gas phase ion energetics 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 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
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tboil | 365. ± 1. | K | AVG | N/A | Average of 14 out of 17 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 187.15 | K | N/A | Dolliver, Gresham, et al., 1938 | Uncertainty assigned by TRC = 1.5 K; TRC |
Tfus | 188.50 | K | N/A | Timmermans, 1922 | Uncertainty assigned by TRC = 0.25 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Tc | 540.70 | K | N/A | Young, 1910 | Uncertainty assigned by TRC = 1. K; TRC |
Tc | 540.70 | K | N/A | Young and Thomas, 1893 | Uncertainty assigned by TRC = 1. K; TRC |
Tc | 546.8 | K | N/A | Pawlewski, 1882 | Uncertainty assigned by TRC = 6. K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Pc | 34.32 | bar | N/A | Young, 1910 | Uncertainty assigned by TRC = 0.8106 bar; TRC |
Pc | 34.304 | bar | N/A | Young and Thomas, 1893 | Uncertainty assigned by TRC = 0.40 bar; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ρc | 2.949 | mol/l | N/A | Young, 1910 | Uncertainty assigned by TRC = 0.098 mol/l; TRC |
ρc | 2.954 | mol/l | N/A | Young and Thomas, 1893 | Uncertainty assigned by TRC = 0.04 mol/l; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 37.42 | kJ/mol | N/A | Majer and Svoboda, 1985 | |
ΔvapH° | 33.4 ± 0.02 | kJ/mol | V | Mathews, 1926 | ALS |
Enthalpy of vaporization
ΔvapH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
32.61 | 365.6 | N/A | Majer and Svoboda, 1985 | |
33.7 | 381. | A | Stephenson and Malanowski, 1987 | Based on data from 366. to 533. K.; AC |
40.1 | 254. | A | Stephenson and Malanowski, 1987 | Based on data from 239. to 366. K. See also Stull, 1947.; 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 |
---|---|---|---|---|---|
239.1 to 365.8 | 4.58354 | 1499.414 | -38.113 | Stull, 1947 | Coefficents calculated by NIST from author's data. |
365.8 to 532.7 | 4.46538 | 1506.866 | -27.723 | Stull, 1947 | Coefficents calculated by NIST from author's data. |
Gas phase ion energetics data
Go To: Top, Phase change 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 evaluated as indicated in comments:
HL - Edward P. Hunter and Sharon G. Lias
Data compiled as indicated in comments:
LBLHLM - Sharon G. Lias, John E. Bartmess, Joel F. Liebman, John L. Holmes, Rhoda D. Levin, and W. Gary Mallard
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron
LL - Sharon G. Lias and Joel F. Liebman
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Proton affinity (review) | 836.6 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
Quantity | Value | Units | Method | Reference | Comment |
Gas basicity | 805.7 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
9.86 | PE | Burgers, Holmes, et al., 1983 | LBLHLM |
9.98 ± 0.02 | PI | Watanabe, Nakayama, et al., 1962 | RDSH |
Appearance energy determinations
Ion | AE (eV) | Other Products | Method | Reference | Comment |
---|---|---|---|---|---|
C2H3O2+ | 11.42 | C3H7 | EI | Holmes, Lossing, et al., 1991 | LL |
C4H7O2+ | 10.28 | CH3 | EI | Burgers, Holmes, et al., 1983 | LBLHLM |
Mass spectrum (electron ionization)
Go To: Top, Phase change 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
Spectrum
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Additional Data
View image of digitized spectrum (can be printed in landscape orientation).
Due to licensing restrictions, this spectrum cannot be downloaded.
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- 10 |
NIST MS number | 228239 |
References
Go To: Top, Phase change data, Gas phase ion energetics data, 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.
Dolliver, Gresham, et al., 1938
Dolliver, M.A.; Gresham, T.L.; Kistiakowsky, G.B.; Smith, E.A.; Vaughan, W.E.,
Heats of Organic Reactions VI. Heats of Hydrogenation of Some Oxygen- Containing Compounds,
J. Am. Chem. Soc., 1938, 60, 440. [all data]
Timmermans, 1922
Timmermans, J.,
Investigation of the Freezing Point of Organic Substances VII,
Bull. Soc. Chim. Belg., 1922, 31, 389. [all data]
Young, 1910
Young, S.,
The Internal Heat of Vaporization constants of thirty pure substances,
Sci. Proc. R. Dublin Soc., 1910, 12, 374. [all data]
Young and Thomas, 1893
Young, S.; Thomas, G.L.,
The vapour pressures, molecular volumes, and critical constants of ten of the lower esters,
J. Chem. Soc., 1893, 63, 1191. [all data]
Pawlewski, 1882
Pawlewski, B.,
The critical temperatures of ester compounds,
Ber. Dtsch. Chem. Ges., 1882, 15, 2460-4. [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]
Mathews, 1926
Mathews, J.H.,
The accurate measurement of heats of vaporization of liquids,
J. Am. Chem. Soc., 1926, 48, 562-576. [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]
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]
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]
Burgers, Holmes, et al., 1983
Burgers, P.C.; Holmes, J.L.; Lossing, F.P.; Povel, F.R.; Terlouw, J.K.,
The role of charge-site location in fragmenting ions. 1- [CH3CHXCOOCH3]+ and [CH2XCH2COOCH3]+ ions and the structures of daughter ions derived from the loss of X (X = I, Br, Cl and CH3),
Org. Mass Spectrom., 1983, 18, 335. [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]
Holmes, Lossing, et al., 1991
Holmes, J.L.; Lossing, F.P.; Mayer, P.M.,
Heats of formation of oxygen-containing organic free radicals from appearance energy measurements,
J. Am. Chem. Soc., 1991, 113, 9723. [all data]
Notes
Go To: Top, Phase change data, Gas phase ion energetics data, Mass spectrum (electron ionization), References
- Symbols used in this document:
AE Appearance energy Pc Critical pressure Tboil Boiling point Tc Critical temperature Tfus Fusion (melting) point ΔvapH Enthalpy of vaporization ΔvapH° Enthalpy of vaporization at standard conditions ρc Critical density - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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