1-Butanol

Formula: C₄H₁₀O
Molecular weight: 74.1216
IUPAC Standard InChI: InChI=1S/C4H10O/c1-2-3-4-5/h5H,2-4H2,1H3
IUPAC Standard InChIKey: LRHPLDYGYMQRHN-UHFFFAOYSA-N
CAS Registry Number: 71-36-3
Chemical structure:
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Other names: Butyl alcohol; n-Butan-1-ol; n-Butanol; n-Butyl alcohol; Butyl hydroxide; CCS 203; Hemostyp; Methylolpropane; Propylcarbinol; n-C4H9OH; Butanol; Butan-1-ol; 1-Hydroxybutane; Alcool butylique; Butanolo; Butylowy alkohol; Butyric alcohol; Propylmethanol; Butanolen; 1-Butyl alcohol; Rcra waste number U031; Butanol-1; NSC 62782
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Gas phase ion energetics data

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Data evaluated as indicated in comments:
HL - Edward P. Hunter and Sharon G. Lias
L - Sharon G. Lias

Data compiled as indicated in comments:
B - John E. Bartmess
LL - Sharon G. Lias and Joel F. Liebman
LBLHLM - Sharon G. Lias, John E. Bartmess, Joel F. Liebman, John L. Holmes, Rhoda D. Levin, and W. Gary Mallard
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron

Quantity	Value	Units	Method	Reference	Comment
IE (evaluated)	9.99 ± 0.05	eV	N/A	N/A	L
Quantity	Value	Units	Method	Reference	Comment
Proton affinity (review)	789.2	kJ/mol	N/A	Hunter and Lias, 1998	HL
Quantity	Value	Units	Method	Reference	Comment
Gas basicity	758.9	kJ/mol	N/A	Hunter and Lias, 1998	HL

Ionization energy determinations

IE (eV)	Method	Reference	Comment
10.10 ± 0.05	EI	Holmes and Lossing, 1991	LL
9.99 ± 0.05	PIPECO	Shao, Baer, et al., 1988	LL
10.64 ± 0.07	EI	Bowen and Maccoll, 1984	LBLHLM
10.09 ± 0.02	PE	Cocksey, Eland, et al., 1971	LLK
10.37	PE	Baker, Betteridge, et al., 1971	LLK
10.37	PE	Baker, Betteridge, et al., 1971	LLK
10.04	PI	Watanabe, Nakayama, et al., 1962	RDSH
10.43	PE	Benoit and Harrison, 1977	Vertical value; LLK
10.44 ± 0.03	PE	Peel and Willett, 1975	Vertical value; LLK
10.37	PE	Katsumata, Iwai, et al., 1973	Vertical value; LLK

Appearance energy determinations

Ion	AE (eV)	Other Products	Method	Reference	Comment
CH₃O⁺	11.36 ± 0.06	n-C₃H₇	EI	Selim and Helal, 1981	LLK
CH₃O⁺	11.46	?	EI	Lambdin, Tuffly, et al., 1959	RDSH
C₂H₂O⁺	11.23	?	EI	Lambdin, Tuffly, et al., 1959	RDSH
C₄H₈⁺	10.18 ± 0.05	H₂O	PIPECO	Shao, Baer, et al., 1988	LL
C₄H₈⁺	10.20 ± 0.10	H₂O	EI	Bowen and Maccoll, 1984	LBLHLM

De-protonation reactions

C₄H₉O^- + = 1-Butanol

By formula: C₄H₉O^- + H⁺ = C₄H₁₀O

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	1570. ± 8.4	kJ/mol	CIDC	Haas and Harrison, 1993	gas phase; Both metastable and 50 eV collision energy.; B
Δ_rH°	1571. ± 8.8	kJ/mol	G+TS	Bartmess, Scott, et al., 1979	gas phase; value altered from reference due to change in acidity scale; B
Δ_rH°	1569. ± 12.	kJ/mol	G+TS	Boand, Houriet, et al., 1983	gas phase; value altered from reference due to change in acidity scale; B
Quantity	Value	Units	Method	Reference	Comment
Δ_rG°	1543. ± 8.8	kJ/mol	H-TS	Haas and Harrison, 1993	gas phase; Both metastable and 50 eV collision energy.; B
Δ_rG°	1543. ± 8.4	kJ/mol	IMRE	Bartmess, Scott, et al., 1979	gas phase; value altered from reference due to change in acidity scale; B
Δ_rG°	1541. ± 12.	kJ/mol	CIDC	Boand, Houriet, et al., 1983	gas phase; value altered from reference due to change in acidity scale; B

References

Go To: Top, Gas phase ion energetics data, Notes

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]

Holmes and Lossing, 1991
Holmes, J.L.; Lossing, F.P., Ionization energies of homologous organic compounds and correlation with molecular size, Org. Mass Spectrom., 1991, 26, 537. [all data]

Shao, Baer, et al., 1988
Shao, J.D.; Baer, T.; Lewis, D.K., Dissociation dynamics of energy-selected ion-dipole complexes. 2. Butyl alcohol ions, J. Phys. Chem., 1988, 92, 5123. [all data]

Bowen and Maccoll, 1984
Bowen, R.D.; Maccoll, A., Low energy, low temperature mass spectra, Org. Mass Spectrom., 1984, 19, 379. [all data]

Cocksey, Eland, et al., 1971
Cocksey, B.J.; Eland, J.H.D.; Danby, C.J., The effect of alkyl substitution on ionisation potential, J. Chem. Soc., 1971, (B), 790. [all data]

Baker, Betteridge, et al., 1971
Baker, A.D.; Betteridge, D.; Kemp, N.R.; Kirby, R.E., Application of photoelectron spectrometry to pesticide analysis. II.Photoelectron spectra of hydroxy-, and halo-alkanes and halohydrins, Anal. Chem., 1971, 43, 375. [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]

Benoit and Harrison, 1977
Benoit, F.M.; Harrison, A.G., Predictive value of proton affinity. Ionization energy correlations involving oxygenated molecules, J. Am. Chem. Soc., 1977, 99, 3980. [all data]

Peel and Willett, 1975
Peel, J.B.; Willett, G.D., Photoelectron spectroscopic studies of the higher alcohols, Aust. J. Chem., 1975, 28, 2357. [all data]

Katsumata, Iwai, et al., 1973
Katsumata, S.; Iwai, T.; Kimura, K., Photoelectron spectra and sum rule consideration. Higher alkyl amines and alcohols, Bull. Chem. Soc. Jpn., 1973, 46, 3391. [all data]

Selim and Helal, 1981
Selim, E.T.M.; Helal, A.I., Heat of formation of CH₂=OH⁺ fragment ion, Indian J. Pure Appl. Phys., 1981, 19, 977. [all data]

Lambdin, Tuffly, et al., 1959
Lambdin, W.J.; Tuffly, B.L.; Yarborough, V.A., Appearance potentials as obtained with an analytical mass spectrometer, Appl. Spectry., 1959, 13, 71. [all data]

Haas and Harrison, 1993
Haas, M.J.; Harrison, A.G., The Fragmentation of Proton-Bound Cluster Ions and the Gas-Phase Acidities of Alcohols, Int. J. Mass Spectrom. Ion Proc., 1993, 124, 2, 115, https://doi.org/10.1016/0168-1176(93)80003-W . [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]

Boand, Houriet, et al., 1983
Boand, G.; Houriet, R.; Baumann, T., The gas phase acidity of aliphatic alcohols, J. Am. Chem. Soc., 1983, 105, 2203. [all data]

Notes

Go To: Top, Gas phase ion energetics data, References

Symbols used in this document:

AE Appearance energy

IE (evaluated) Recommended ionization energy

Δ_rG° Free energy of reaction at standard conditions

Δ_rH° Enthalpy of reaction at standard conditions
Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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AE	Appearance energy
IE (evaluated)	Recommended ionization energy
Δ_rG°	Free energy of reaction at standard conditions
Δ_rH°	Enthalpy of reaction at standard conditions