Butanal - The NIST WebBook

Butanal

• Formula: C4H8O
• Molecular weight: 72.1057
• IUPAC Standard InChI: InChI=1S/C4H8O/c1-2-3-4-5/h4H,2-3H2,1H3 Copy
• IUPAC Standard InChIKey: ZTQSAGDEMFDKMZ-UHFFFAOYSA-N Copy
• CAS Registry Number: 123-72-8
• Chemical structure: This structure is also available as a 2d Mol file or as a computed 3d SD file View 3d structure (requires JavaScript / HTML 5)
• Other names: Butyraldehyde; n-Butanal; n-Butyl aldehyde; n-Butyraldehyde; Butal; Butaldehyde; Butanaldehyde; Butyl aldehyde; Butyral; Butyric aldehyde; Butyrylaldehyde; n-C3H7CHO; Aldehyde butyrique; Aldeide butirrica; Butalyde; Butyraldehyd; NCI-C56291; UN 1129; 1-Butanal; Butan-1-al; NSC 62779
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• Information on this page:
  • Reaction thermochemistry data
  • References
  • Notes
• Other data available:
  • Gas phase thermochemistry data
  • Condensed phase thermochemistry data
  • Phase change data
  • Henry's Law data
  • Gas phase ion energetics data
  • Ion clustering data
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • UV/Visible spectrum
  • Gas Chromatography
• Data at other public NIST sites:
  • Gas Phase Kinetics Database
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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 as indicated in comments: B - John E. Bartmess M - Michael M. Meot-Ner (Mautner) and Sharon G. Lias ALS - 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

C4H7O- + =

By formula: C4H7O- + H+ = C4H8O

Quantity	Value	Units	Method	Reference	Comment
ΔrH°	1526. ± 8.8	kJ/mol	D-EA	Alconcel, Deyerl, et al., 2001	gas phase; B
ΔrH°	1523. ± 9.6	kJ/mol	D-EA	Zimmerman, Reed, et al., 1977	gas phase; B
Quantity	Value	Units	Method	Reference	Comment
ΔrG°	1499. ± 9.6	kJ/mol	H-TS	Alconcel, Deyerl, et al., 2001	gas phase; B
ΔrG°	1496. ± 10.	kJ/mol	H-TS	Zimmerman, Reed, et al., 1977	gas phase; B

+ = ( • )

By formula: NO- + C4H8O = (NO- • C4H8O)

Quantity	Value	Units	Method	Reference	Comment
ΔrH°	164.	kJ/mol	ICR	Reents and Freiser, 1981	gas phase; switching reaction,Thermochemical ladder(NO+)C2H5OH, Entropy change calculated or estimated; Farid and McMahon, 1978; M

+ = + 2

By formula: C6H14O2 + H2O = C4H8O + 2CH4O

Quantity	Value	Units	Method	Reference	Comment
ΔrH°	36.2 ± 0.1	kJ/mol	Cm	Wiberg, Morgan, et al., 1994	liquid phase; ALS
ΔrH°	36.53 ± 0.096	kJ/mol	Eqk	Wiberg and Squires, 1981	liquid phase; ALS

+ =

By formula: H2 + C4H6O = C4H8O

Quantity	Value	Units	Method	Reference	Comment
ΔrH°	-104.2 ± 0.42	kJ/mol	Chyd	Dolliver, Gresham, et al., 1938	gas phase; Reanalyzed by Cox and Pilcher, 1970, Original value = -105.3 ± 0.4 kJ/mol; At 355°K; ALS

(CAS Reg. No. 26232-84-8 • 4294967295) + = CAS Reg. No. 26232-84-8

By formula: (CAS Reg. No. 26232-84-8 • 4294967295C4H8O) + C4H8O = CAS Reg. No. 26232-84-8

Quantity	Value	Units	Method	Reference	Comment
ΔrH°	175. ± 9.2	kJ/mol	N/A	Bartmess, Scott, et al., 1979	gas phase; value altered from reference due to change in acidity scale; B

+ =

By formula: C4H8O + H2 = C4H10O

Quantity	Value	Units	Method	Reference	Comment
ΔrH°	-81.88 ± 0.75	kJ/mol	Cm	Wiberg, Crocker, et al., 1991	liquid phase; ALS
ΔrH°	-70.5 ± 1.3	kJ/mol	Chyd	Buckley and Cox, 1967	gas phase; ALS

+ = ( • )

By formula: Mg+ + C4H8O = (Mg+ • C4H8O)

Quantity	Value	Units	Method	Reference	Comment
ΔrH°	280. ± 20.	kJ/mol	ICR	Operti, Tews, et al., 1988	gas phase; switching reaction,Thermochemical ladder(Mg+)CH3OH; M

+ 2 = +

By formula: C4H8O + 2CH4O = C6H14O2 + H2O

Quantity	Value	Units	Method	Reference	Comment
ΔrH°	-59. ± 1.	kJ/mol	Cm	Wiberg, Morgan, et al., 1994	gas phase; ALS

3 =

By formula: 3C4H8O = C12H24O3

Quantity	Value	Units	Method	Reference	Comment
ΔrH°	-29.45	kJ/mol	Eqk	Ogorodnikov, Katsnel'son, et al., 1990	liquid phase; PMR; ALS

References

Go To: Top, Reaction thermochemistry data, Notes

Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Alconcel, Deyerl, et al., 2001 Alconcel, L.S.; Deyerl, H.J.; Continetti, R.E., Effects of alkyl substitution on the energetics of enolate anions and radicals, J. Am. Chem. Soc., 2001, 123, 50, 12675-12681, https://doi.org/10.1021/ja0120431 . [all data]

Zimmerman, Reed, et al., 1977 Zimmerman, A.H.; Reed, K.J.; Brauman, J.I., Photodetachment of electrons from enolate anions. Gas phase electron affinities of enolate radicals, J. Am. Chem. Soc., 1977, 99, 7203. [all data]

Reents and Freiser, 1981 Reents, W.D.; Freiser, B.S., Gas-Phase Binding Energies and Spectroscopic Properties of NO+ Charge-Transfer Complexes, J. Am. Chem. Soc., 1981, 103, 2791. [all data]

Farid and McMahon, 1978 Farid, R.; McMahon, T.B., Gas-Phase Ion-Molecule Reactions of Alkyl Nitrites by Ion Cyclotron Resonance Spectroscopy, Int. J. Mass Spectrom. Ion Phys., 1978, 27, 2, 163, https://doi.org/10.1016/0020-7381(78)80037-0 . [all data]

Wiberg, Morgan, et al., 1994 Wiberg, K.B.; Morgan, K.M.; Maltz, H., Thermochemistry of carbonyl reactions. 6. A study of hydration equilibria, J. Am. Chem. Soc., 1994, 116, 11067-11077. [all data]

Wiberg and Squires, 1981 Wiberg, K.B.; Squires, R.R., Thermochemical studies of carbonyl reactions. 2. Steric effects in acetal and ketal hydrolysis, J. Am. Chem. Soc., 1981, 103, 4473-4478. [all data]

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, 440-450. [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]

Bartmess, Scott, et al., 1979 Bartmess, J.E.; Scott, J.A.; McIver, R.T., Jr., The gas phase acidity scale from methanol to phenol, J. Am. Chem. Soc., 1979, 101, 6047. [all data]

Wiberg, Crocker, et al., 1991 Wiberg, K.B.; Crocker, L.S.; Morgan, K.M., Thermochemical studies of carbonyl compounds. 5. Enthalpies of reduction of carbonyl groups, J. Am. Chem. Soc., 1991, 113, 3447-3450. [all data]

Buckley and Cox, 1967 Buckley, E.; Cox, J.D., Chemical equilibria. Part 2.-Dehydrogenation of propanol and butanol, Trans. Faraday Soc., 1967, 63, 895-901. [all data]

Operti, Tews, et al., 1988 Operti, L.; Tews, E.C.; Freiser, B.S., Determination of Gas-Phase Ligand Binding Energies to Mg+ by FTMS Techniques, J. Am. Chem. Soc., 1988, 110, 12, 3847, https://doi.org/10.1021/ja00220a020 . [all data]

Ogorodnikov, Katsnel'son, et al., 1990 Ogorodnikov, A.L.; Katsnel'son, M.G.; Pinson, V.V.; Levin, Yu.V., Study of thermodynamic characteristics of a butyraldehyde-cyclic trimer system, Zh. Prikl. Khim. (Leningrad), 1990, 63, 1340-1343. [all data]

Notes

Go To: Top, Reaction thermochemistry data, References

• Symbols used in this document:

  ΔrG°	Free energy of reaction at standard conditions
  ΔrH°	Enthalpy of reaction at standard conditions

• Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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