Isobutylamine
- Formula: C4H11N
- Molecular weight: 73.1368
- IUPAC Standard InChIKey: KDSNLYIMUZNERS-UHFFFAOYSA-N
- CAS Registry Number: 78-81-9
- 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: 1-Propanamine, 2-methyl-; Monoisobutylamine; Valamine; 1-Amino-2-methylpropane; 2-Methylpropylamine; 3-Methyl-2-propylamine; iso-C4H9NH2; 2-Methyl-1-Aminopropane; 2-Methyl-1-propanamine; UN 1214; i-Butylamine; 2-Methylpropanamine; NSC 8028
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Gas phase thermochemistry data
Go To: Top, Condensed phase thermochemistry data, 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 as indicated in comments:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DRB - Donald R. Burgess, Jr.
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°gas | -23.57 ± 0.13 | kcal/mol | Ccr | Good and Moore, 1970 | ALS |
ΔfH°gas | -34.44 | kcal/mol | N/A | Lemoult, 1907 | Value computed using ΔfHliquid° value of -178.0 kj/mol from Lemoult, 1907 and ΔvapH° value of 33.9 kj/mol from Good and Moore, 1970.; DRB |
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 |
---|---|---|---|---|---|
ΔfH°liquid | -31.68 ± 0.12 | kcal/mol | Ccr | Good and Moore, 1970 | ALS |
ΔfH°liquid | -42.6 | kcal/mol | Ccb | Lemoult, 1907 | ALS |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°liquid | -720.25 ± 0.10 | kcal/mol | Ccr | Good and Moore, 1970 | ALS |
ΔcH°liquid | -714.0 | kcal/mol | Ccb | Lemoult, 1907 | ALS |
Constant pressure heat capacity of liquid
Cp,liquid (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
46.4 | 298.15 | Konicek and Wadso, 1971 | 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
DRB - Donald R. Burgess, Jr.
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tboil | 341. ± 1. | K | AVG | N/A | Average of 9 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 186.5 | K | N/A | Simon and Huter, 1935 | Uncertainty assigned by TRC = 0.5 K; TRC |
Tfus | 188.55 | K | N/A | Simon and Huter, 1935, 2 | Uncertainty assigned by TRC = 1.5 K; TRC |
Tfus | 187.65 | K | N/A | Timmermans and Mattaar, 1921 | Uncertainty assigned by TRC = 0.5 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Tc | 516.9 | K | N/A | Majer and Svoboda, 1985 | |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 8.10 ± 0.03 | kcal/mol | AVG | N/A | Average of 7 values; Individual data points |
Enthalpy of vaporization
ΔvapH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
7.316 | 340.7 | N/A | Majer and Svoboda, 1985 | |
8.99 | 263. | A | Stephenson and Malanowski, 1987 | Based on data from 248. to 347. K.; AC |
7.82 ± 0.02 | 313. | C | Majer, Svoboda, et al., 1979 | AC |
7.55 ± 0.02 | 328. | C | Majer, Svoboda, et al., 1979 | AC |
8.01 | 313. | EB | Majer, Svoboda, et al., 1979 | Based on data from 297. to 340. K.; AC |
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 328. | 13.10 | 0.3355 | 516.9 | Majer 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 |
---|---|---|---|---|---|
223. to 341.8 | 4.40733 | 1317.873 | -42.421 | Stull, 1947 | Coefficents calculated by NIST from author's data. |
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
Data compiled as indicated in comments:
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron
LL - Sharon G. Lias and Joel F. Liebman
View reactions leading to C4H11N+ (ion structure unspecified)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Proton affinity (review) | 221.0 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
Quantity | Value | Units | Method | Reference | Comment |
Gas basicity | 212.9 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
8.5 ± 0.1 | PE | Aue, Webb, et al., 1976 | LLK |
8.70 | PI | Watanabe, Nakayama, et al., 1962 | RDSH |
Appearance energy determinations
Ion | AE (eV) | Other Products | Method | Reference | Comment |
---|---|---|---|---|---|
CH4N+ | 9.52 | 2-C3H7 | EI | Holmes, Lossing, et al., 1988 | LL |
C2H6N+ | 9.03 | C2H5 | EI | Lossing, Lam, et al., 1981 | LLK |
References
Go To: Top, Gas phase thermochemistry data, Condensed 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.
Good and Moore, 1970
Good, W.D.; Moore, R.T.,
Enthalpies of formation of ethylenediamine, 1,2,-propanediamine, 1,2,-butanediamine, 2-methyl-1,2-propanediamine, and isobutylamine C-N and N-F Thermochemical bond energies,
J. Chem. Eng. Data, 1970, 15, 150-154. [all data]
Lemoult, 1907
Lemoult, M.P.,
Recherches theoriques et experimentales sur les chaleurs de combustion et de formation des composes organiques,
Ann. Chim. Phys., 1907, 12, 395-432. [all data]
Konicek and Wadso, 1971
Konicek, J.; Wadso, I.,
Thermochemical properties of some carboxylic acids, amines and N-substituted amides in aqueous solution,
Acta Chem. Scand., 1971, 25, 1541-1551. [all data]
Simon and Huter, 1935
Simon, A.; Huter, J.,
Vapor Pressure Curves, Melting Point and Chemical Constants of Dimethyl, Trimethyl- and Isobutylamines,
Z. Elektrochem., 1935, 41, 28. [all data]
Simon and Huter, 1935, 2
Simon, A.; Huter, J.,
Z. Elektrochem., 1935, 41, 294. [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]
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]
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]
Majer, Svoboda, et al., 1979
Majer, Vladimír; Svoboda, Václav; Koubek, Josef; Pick, Jirí,
Temperature dependence of heats of vaporization, saturated vapour pressures and cohesive energies for a group of amines,
Collect. Czech. Chem. Commun., 1979, 44, 12, 3521-3528, https://doi.org/10.1135/cccc19793521
. [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]
Aue, Webb, et al., 1976
Aue, D.H.; Webb, H.M.; Bowers, M.T.,
Quantitative proton affinities, ionization potentials, and hydrogen affinities of alkylamines,
J. Am. Chem. Soc., 1976, 98, 311. [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., 1988
Holmes, J.L.; Lossing, F.P.; Maccoll, A.,
Heats of formation of alkyl radicals from appearance energies,
J. Am. Chem. Soc., 1988, 110, 7339. [all data]
Lossing, Lam, et al., 1981
Lossing, F.P.; Lam, Y.-T.; Maccoll, A.,
Gas phase heats of formation of alkyl immonium ions,
Can. J. Chem., 1981, 59, 2228. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, References
- Symbols used in this document:
AE Appearance energy Cp,liquid Constant pressure heat capacity of liquid Tboil Boiling point Tc Critical temperature Tfus Fusion (melting) point ΔcH°liquid Enthalpy of combustion of liquid at standard conditions ΔfH°gas Enthalpy of formation of gas at standard conditions ΔfH°liquid Enthalpy of formation of liquid at standard conditions ΔvapH Enthalpy of vaporization ΔvapH° Enthalpy of vaporization at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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