Acetamide, N-butyl-

Formula: C₆H₁₃NO
Molecular weight: 115.1735
IUPAC Standard InChI: InChI=1S/C6H13NO/c1-3-4-5-7-6(2)8/h3-5H2,1-2H3,(H,7,8)
IUPAC Standard InChIKey: GYLDXXLJMRTVSS-UHFFFAOYSA-N
CAS Registry Number: 1119-49-9
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: N-Butylacetamide; N-n-Butylacetamide
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Reaction thermochemistry data

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Data compiled by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

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

+ = Acetamide, N-butyl- +

By formula: C₄H₆O₃ + C₄H₁₁N = C₆H₁₃NO + C₂H₄O₂

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	-113.2 ± 0.46	kJ/mol	Cm	Wadso, 1962	liquid phase
Δ_rH°	-163.7 ± 0.3	kJ/mol	Cm	Wadso, 1958	liquid phase; Heat of aminolysis

Acetamide, N-butyl- + = +

By formula: C₆H₁₃NO + C₂H₄O₂ = C₈H₁₅NO₂ + H₂O

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	40.5 ± 0.50	kJ/mol	Cm	Wadso, 1965	liquid phase; Heat of hydrolysis

+ = + Acetamide, N-butyl-

By formula: C₄H₁₁N + C₆H₁₂OS = C₄H₁₀S + C₆H₁₃NO

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	-57.74 ± 0.63	kJ/mol	Cm	Wadso, 1958	liquid phase; Heat of aminolysis

+ = Acetamide, N-butyl- +

By formula: C₄H₁₁N + C₄H₅N₃O = C₆H₁₃NO + C₂H₃N₃

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	-85.8 ± 0.3	kJ/mol	Cm	Wadso, 1962	solid phase

+ = Acetamide, N-butyl- +

By formula: C₄H₁₁N + C₅H₆N₂O = C₆H₁₃NO + C₃H₄N₂

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	-75.6 ± 0.3	kJ/mol	Cm	Wadso, 1962	solid phase

Acetamide, N-butyl- + = +

By formula: C₆H₁₃NO + H₂O = C₄H₁₁N + C₂H₄O₂

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	55.2 ± 0.2	kJ/mol	Cm	Wadso, 1962	liquid phase

Gas Chromatography

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Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director

Kovats' RI, non-polar column, isothermal

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Column type	Active phase	Temperature (C)	I	Reference	Comment
Packed	SE-30	180.	1090.	Krawczyk and Piotrowski, 1989	N2, Chromosorb W AW; Column length: 1. m
Packed	Apiezon L	150.	1057.	Zhuravleva I.L., Golovnya R.V., et al., 1978	N2, Chromosorb G-AW; Column length: 2.7 m

Kovats' RI, polar column, isothermal

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Column type	Active phase	Temperature (C)	I	Reference	Comment
Packed	Polyethylene Glycol	150.	1885.	Zhuravleva I.L., Golovnya R.V., et al., 1978	N2, Chromosorb G-AW; Column length: 2.7 m

Normal alkane RI, non-polar column, custom temperature program

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Column type	Active phase	I	Reference	Comment
Capillary	Polydimethyl siloxanes	1057.	Zenkevich and Chupalov, 1996	Program: not specified

References

Go To: Top, Reaction thermochemistry data, Gas Chromatography, Notes

Wadso, 1962
Wadso, I., Heats of aminolysis and hydrolysis of some N-acetyl compounds and of acetic anhydride, Acta Chem. Scand., 1962, 16, 471-478. [all data]

Wadso, 1958
Wadso, I., The heats of aminolysis of n-butyl thiolacetate and acetic anhydride, Acta Chem. Scand., 1958, 12, 635-640. [all data]

Wadso, 1965
Wadso, I., Thermochemical properties of diacetimide, N-butyldiacetimide and N-phenyldiacetimide, Acta Chem. Scand., 1965, 19, 1079-1087. [all data]

Krawczyk and Piotrowski, 1989
Krawczyk, W.; Piotrowski, G.T., Relationships Between Structure and Retention Index for N-Substituted Amides of Aliphatic Acids on a Non-Polar Column, J. Chromatogr., 1989, 463, 297-304, https://doi.org/10.1016/S0021-9673(01)84484-8 . [all data]

Zhuravleva I.L., Golovnya R.V., et al., 1978
Zhuravleva I.L.; Golovnya R.V.; Palamarchuk L.F.; Kishkovskii Z.N., Gas-chromatographic determination of N-monoalkylacetamides, J. Anal. Chem. USSR (Engl. Transl.), 1978, 33, 11, 1717-1719. [all data]

Zenkevich and Chupalov, 1996
Zenkevich, I.G.; Chupalov, A.A., New Possibilities of Chromato Mass Pectrometric Identification of Organic Compounds Using Increments of Gas Chromatographic Retention Indices of Molecular Structural Fragments, Zh. Org. Khim. (Rus.), 1996, 32, 5, 656-666. [all data]

Notes

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Symbols used in this document:

Δ_rH° Enthalpy of reaction at standard conditions
Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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