2-Propanamine, 2-methyl-

Formula: C₄H₁₁N
Molecular weight: 73.1368
IUPAC Standard InChI: InChI=1S/C4H11N/c1-4(2,3)5/h5H2,1-3H3
IUPAC Standard InChIKey: YBRBMKDOPFTVDT-UHFFFAOYSA-N
CAS Registry Number: 75-64-9
Chemical structure:
This structure is also available as a 2d Mol file or as a computed 3d SD file
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Other names: tert-Butylamine; Trimethylaminomethane; 1,1-Dimethylethylamine; 2-Amino-2-Methylpropane; 2-Aminoisobutane; 2-Methyl-2-aminopropane; 2-Methyl-2-propylamine; tert-C4H9NH2; 2-Methyl-2-propanamine; t-Butylamine; Butylamine, tert; Butylamine, tertiary; 1,1-Dimethylethanamine; 1-Amino-1,1-dimethylethane; Erbumine; NSC 9571
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Gas phase thermochemistry data

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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
Δ_fH°_gas	-120. ± 0.8	kJ/mol	Cm	Scott, 1971	ALS
Δ_fH°_gas	-120.9 ± 0.63	kJ/mol	Ccr	Smith and Good, 1967	ALS
Δ_fH°_gas	-120.3	kJ/mol	N/A	Evans, Fairbrother, et al., 1959	Value computed using Δ_fH_liquid° value of -150.0±1.0 kj/mol from Evans, Fairbrother, et al., 1959 and Δ_vapH° value of 29.7 kj/mol from Smith and Good, 1967.; DRB
Δ_fH°_gas	-139.3	kJ/mol	N/A	Lemoult, 1907	Value computed using Δ_fH_liquid° value of -169.0 kj/mol from Lemoult, 1907 and Δ_vapH° value of 29.7 kj/mol from Smith and Good, 1967.; DRB

Condensed phase thermochemistry data

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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
Δ_fH°_liquid	-150.6 ± 0.50	kJ/mol	Ccr	Smith and Good, 1967	ALS
Δ_fH°_liquid	-150. ± 1.	kJ/mol	Ccb	Evans, Fairbrother, et al., 1959	ALS
Δ_fH°_liquid	-169.	kJ/mol	Ccb	Lemoult, 1907	ALS
Quantity	Value	Units	Method	Reference	Comment
Δ_cH°_liquid	-2995.5 ± 0.42	kJ/mol	Ccr	Smith and Good, 1967	ALS
Δ_cH°_liquid	-2995.8 ± 1.1	kJ/mol	Ccb	Evans, Fairbrother, et al., 1959	ALS
Δ_cH°_liquid	-2997.	kJ/mol	Ccb	Lemoult, 1907	ALS
Quantity	Value	Units	Method	Reference	Comment
S°_liquid	233.63	J/mol*K	N/A	Finke, Messerly, et al., 1972	DH

Constant pressure heat capacity of liquid

C_p,liquid (J/mol*K)	Temperature (K)	Reference	Comment
191.71	298.15	Finke, Messerly, et al., 1972	T = 12 to 350 K.; DH
190.	298.15	Konicek and Wadso, 1971	DH
192.0	298.15	Smith and Good, 1967	DH

Gas phase ion energetics data

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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

View reactions leading to C₄H₁₁N⁺ (ion structure unspecified)

Quantity	Value	Units	Method	Reference	Comment
Proton affinity (review)	934.1	kJ/mol	N/A	Hunter and Lias, 1998	HL
Quantity	Value	Units	Method	Reference	Comment
Gas basicity	899.9	kJ/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
8.83	PE	Al-Joboury and Turner, 1964	RDSH
8.64	PI	Watanabe, Nakayama, et al., 1962	RDSH

Appearance energy determinations

Ion	AE (eV)	Other Products	Method	Reference	Comment
C₃H₈N⁺	8.89	CH₃	EI	Lossing, Lam, et al., 1981	LLK

References

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Scott, 1971
Scott, D.W., 1-Aminopropane, 2-aminopropane, and 2-methyl-2-aminopropane. Vibrational assignments, conformational analyses, and chemical thermodynamic properties, J. Chem. Thermodyn., 1971, 3, 843-852. [all data]

Smith and Good, 1967
Smith, N.K.; Good, W.D., Enthalpies of combustion and formation of propylamine, isopropylamine, and tert-butylamine, J. Chem. Eng. Data, 1967, 12, 572-574. [all data]

Evans, Fairbrother, et al., 1959
Evans, F.W.; Fairbrother, D.M.; Skinner, H.A., The heats of combustion of organic compounds of nitrogen Part 3.-Butylamines, and the cis-dimer of nitrosoisobutane, Trans. Faraday Soc., 1959, 55, 399-403. [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]

Finke, Messerly, et al., 1972
Finke, H.L.; Messerly, J.F.; Todd, S.S., Thermodynamic properties of acrylonitrile, 1-aminopropane, 2-aminopropane, and 2-methyl-2-aminopropane, J. Chem. Thermodynam., 1972, 4, 359-374. [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]

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]

Al-Joboury and Turner, 1964
Al-Joboury, M.I.; Turner, D.W., Molecular photoelectron spectroscopy. Part II. A summary of ionization potentials, J. Chem. Soc., 1964, 4434. [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]

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

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Symbols used in this document:

AE	Appearance energy
C_p,liquid	Constant pressure heat capacity of liquid
S°_liquid	Entropy of liquid at standard conditions
Δ_cH°_liquid	Enthalpy of combustion of liquid at standard conditions
Δ_fH°_gas	Enthalpy of formation of gas at standard conditions
Δ_fH°_liquid	Enthalpy of formation of liquid at standard conditions

Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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