2-Butanol

Formula: C₄H₁₀O
Molecular weight: 74.1216
IUPAC Standard InChI: InChI=1S/C4H10O/c1-3-4(2)5/h4-5H,3H2,1-2H3
IUPAC Standard InChIKey: BTANRVKWQNVYAZ-UHFFFAOYSA-N
CAS Registry Number: 78-92-2
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.
Species with the same structure:
- 2-Butanol
Stereoisomers:
- 2-Butanol, (R)-
- (S)-butan-2-ol
Other names: sec-Butyl Alcohol; sec-Butanol; CCS 301; Ethyl methyl carbinol; Methyl ethyl carbinol; 1-Methyl-1-propanol; 1-Methylpropyl alcohol; 2-Hydroxybutane; sec-C4H9OH; Butane, 2-hydroxy-; Butanol-2; Butan-2-ol; 2-Butyl alcohol; s-Butyl alcohol; Butylene hydrate; DL-sec-Butanol; DL-2-Butanol; Alcool butylique secondaire; Butanol secondaire; s-Butanol; 1-Methyl propanol; n-Butan-2-ol; NSC 25499
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Gas phase thermochemistry data

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Data compiled as indicated in comments:
DRB - Donald R. Burgess, Jr.
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
GT - Glushko Thermocenter, Russian Academy of Sciences, Moscow

Quantity	Value	Units	Method	Reference	Comment
Δ_fH°_gas	-293.1	kJ/mol	N/A	Chao and Rossini, 1965	Value computed using Δ_fH_liquid° value of -342.7±0.6 kj/mol from Chao and Rossini, 1965 and Δ_vapH° value of 49.6 kj/mol from Skinner and Snelson, 1960.; DRB
Δ_fH°_gas	-293. ± 1.5	kJ/mol	Ccb	Skinner and Snelson, 1960	ALS
Quantity	Value	Units	Method	Reference	Comment
S°_gas	355.37	J/mol*K	N/A	Chao J., 1986	p=1 bar. Other third-law value of entropy at 298.15 K is 357.2 J/molK [ Andon R.J.L., 1971]. The value of S(298.15 K)=358.5 J/molK was obtained from equilibrium studies [ Buckley E., 1965].; GT

Constant pressure heat capacity of gas

C_p,gas (J/mol*K)	Temperature (K)	Reference	Comment
41.87	50.	Thermodynamics Research Center, 1997	p=1 bar. Calculated entropy at 298.15 K is 4.1 J/molK higher than the third-law value. Authors [ Chao J., 1986] believe that this is greater than the expected experimental uncertainty and reflects the approximations made in the calculated value. However, it should be noted that other experimental values of S(298.15 K), 357.2 [ Andon R.J.L., 1971] and 358.5 J/molK [ Buckley E., 1965], are in better agreement with calculated value. Selected S(T) and Cp(T) values agree with other statistically calculated values [62BER/MCC] within 1 J/molK. Values calculated by [ Rodionov P.P., 1969] are up to 9 and 11 J/molK lower than selected ones fo Cp(T) and S(T) values, respectively. Please also see Chao J., 1986.; GT
59.06	100.
74.17	150.
86.94	200.
105.90	273.15
112.74 ± 0.17	298.15
113.25	300.
140.74	400.
165.63	500.
186.83	600.
204.82	700.
220.27	800.
233.65	900.
245.30	1000.
255.45	1100.
264.30	1200.
272.03	1300.
278.77	1400.
284.66	1500.
296.4	1750.
304.9	2000.
311.2	2250.
315.9	2500.
319.4	2750.
322.1	3000.

Constant pressure heat capacity of gas

C_p,gas (J/mol*K)	Temperature (K)	Reference	Comment
131.71 ± 0.40	365.15	Stromsoe E., 1970	Ideal gas heat capacities are given by [ Stromsoe E., 1970] as a linear function Cp=f1(a+bT). This expression approximates the experimental values with the average deviation of 0.67 J/molK. The accuracy of the experimental heat capacities [ Stromsoe E., 1970] is estimated as less than 0.3%. Please also see Berman N.S., 1962.; GT
137.87 ± 0.67	380.95
136.52 ± 0.41	383.15
139.10 ± 0.67	386.25
140.85 ± 0.67	393.75
141.46 ± 0.42	401.15
143.50 ± 0.67	405.15
143.74 ± 0.67	406.15
146.32 ± 0.67	417.25
146.23 ± 0.44	419.15
150.96 ± 0.45	437.15
151.79 ± 0.67	440.75
155.64 ± 0.47	455.15
158.81 ± 0.67	470.85
169.31 ± 0.67	515.95
179.65 ± 0.67	560.35
184.89 ± 0.67	582.85

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	-342.7 ± 0.59	kJ/mol	Ccb	Chao and Rossini, 1965	see Rossini, 1934; ALS
Δ_fH°_liquid	-342.6 ± 0.92	kJ/mol	Ccb	Skinner and Snelson, 1960	ALS
Quantity	Value	Units	Method	Reference	Comment
Δ_cH°_liquid	-2660.6 ± 0.54	kJ/mol	Ccb	Chao and Rossini, 1965	see Rossini, 1934; Corresponding Δ_fHº_liquid = -342.6 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS
Δ_cH°_liquid	-2660.6 ± 0.92	kJ/mol	Ccb	Skinner and Snelson, 1960	Corresponding Δ_fHº_liquid = -342.5 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS
Quantity	Value	Units	Method	Reference	Comment
S°_liquid	213.1	J/mol*K	N/A	Andon, Connett, et al., 1971	DH
S°_liquid	214.7	J/mol*K	N/A	Andon, Connett, et al., 1971	DH

Constant pressure heat capacity of liquid

C_p,liquid (J/mol*K)	Temperature (K)	Reference	Comment
197.1	298.15	N/A	DH
198.03	298.15	Okano, Ogawa, et al., 1988	DH
196.67	298.15	Piekarski and Somsen, 1988	DH
199.2	298.	Conti, Gianni, et al., 1976	DH
197.4	298.15	Andon, Connett, et al., 1971	T = 11 to 350 K.; DH
196.8	298.15	Andon, Connett, et al., 1971	T = 11 to 350 K.; DH
184.9	281.7	Parks, Thomas, et al., 1936	T = 103 to 282 K. Glass at lower temperature. Unsmoothed experimental datum.; DH

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)	9.88 ± 0.03	eV	N/A	N/A	L
Quantity	Value	Units	Method	Reference	Comment
Proton affinity (review)	815.	kJ/mol	N/A	Hunter and Lias, 1998	HL
Quantity	Value	Units	Method	Reference	Comment
Gas basicity	784.6	kJ/mol	N/A	Hunter and Lias, 1998	HL

Ionization energy determinations

IE (eV)	Method	Reference	Comment
9.88 ± 0.03	PIPECO	Shao, Baer, et al., 1988	LL
9.88 ± 0.07	EI	Bowen and Maccoll, 1984	LBLHLM
9.88	EI	Holmes, Burgers, et al., 1982	LBLHLM
9.88	EI	Holmes, Fingas, et al., 1981	LLK
10.23	PE	Benoit and Harrison, 1977	Vertical value; LLK
10.35 ± 0.03	PE	Peel and Willett, 1975	Vertical value; LLK

Appearance energy determinations

Ion	AE (eV)	Other Products	Method	Reference	Comment
CH₃O⁺	12.2 ± 0.1	C₂H₄+CH₃	EI	Burgers and Holmes, 1982	LBLHLM
CH₃O⁺	12.40	?	EI	Holmes, Rye, et al., 1979	LLK
CH₃O⁺	12.5	?	EI	Harrison, Ivko, et al., 1966	RDSH
C₂H₄O⁺	10.05 ± 0.02	C₂H₆	PIPECO	Shao, Baer, et al., 1988	LL
C₂H₄O⁺	10.12	C₂H₆	EI	Bowen and Maccoll, 1984	LBLHLM
C₂H₄O⁺	10.12	C₂H₆	EI	Holmes, Burgers, et al., 1982	LBLHLM
C₂H₅O⁺	10.20 ± 0.02	C₂H₅	PIPECO	Shao, Baer, et al., 1988	LL
C₂H₅O⁺	10.22	C₂H₅	EI	Holmes, Lossing, et al., 1988	LL
C₂H₅O⁺	10.22 ± 0.08	C₂H₅	EI	Bowen and Maccoll, 1984	LBLHLM
C₂H₅O⁺	10.18	C₂H₅	EI	Holmes, Burgers, et al., 1982	LBLHLM
C₂H₅O⁺	10.22	C₂H₅	EI	Lossing, 1977	LLK
C₂H₅O⁺	10.4	C₂H₅	EI	Harrison, Ivko, et al., 1966	RDSH
C₃H₅⁺	12.0 ± 0.1	CH₃+H₂O	EI	Burgers and Holmes, 1982	LBLHLM
C₃H₆O⁺	10.22	CH₄	EI	Holmes, Burgers, et al., 1982	LBLHLM
C₃H₇O⁺	10.14 ± 0.02	CH₃	PIPECO	Shao, Baer, et al., 1988	LL
C₃H₇O⁺	10.18 ± 0.08	CH₃	EI	Bowen and Maccoll, 1984	LBLHLM
C₃H₇O⁺	10.24	CH₃	EI	Holmes, Burgers, et al., 1982	LBLHLM
C₃H₇O⁺	10.18	CH₃	EI	Lossing, 1977	LLK
C₃H₇O⁺	10.7	CH₃	EI	Harrison, Ivko, et al., 1966	RDSH
C₃H₈O⁺	10.22	CH₄	EI	Bowen and Maccoll, 1984	LBLHLM

De-protonation reactions

C₄H₉O^- + = 2-Butanol

By formula: C₄H₉O^- + H⁺ = C₄H₁₀O

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	1565. ± 8.4	kJ/mol	CIDC	Haas and Harrison, 1993	gas phase; Both metastable and 50 eV collision energy.; B
Δ_rH°	1566. ± 8.8	kJ/mol	G+TS	Taft, 1987	gas phase; value altered from reference due to change in acidity scale; B
Δ_rH°	1565. ± 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°	1538. ± 8.8	kJ/mol	H-TS	Haas and Harrison, 1993	gas phase; Both metastable and 50 eV collision energy.; B
Δ_rG°	1538. ± 8.4	kJ/mol	IMRE	Taft, 1987	gas phase; value altered from reference due to change in acidity scale; B
Δ_rG°	1538. ± 11.	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 thermochemistry data, Condensed phase thermochemistry data, Gas phase ion energetics data, Notes

Chao and Rossini, 1965
Chao, J.; Rossini, F.D., Heats of combustion, formation, and isomerization of nineteen alkanols, J. Chem. Eng. Data, 1965, 10, 374-379. [all data]

Skinner and Snelson, 1960
Skinner, H.A.; Snelson, A., The heats of combustion of the four isomeric butyl alcohols, Trans. Faraday Soc., 1960, 56, 1776-1783. [all data]

Chao J., 1986
Chao J., Thermodynamic properties of key organic oxygen compounds in the carbon range C1 to C4. Part 2. Ideal gas properties, J. Phys. Chem. Ref. Data, 1986, 15, 1369-1436. [all data]

Andon R.J.L., 1971
Andon R.J.L., Thermodynamic properties of organic oxygen compounds. Part XXVII. (+/-)-Butan-2-ol and (+)-butan-2-ol, J. Chem. Soc. A, 1971, 661-664. [all data]

Buckley E., 1965
Buckley E., Equilibria in some secondary alcohol + hydrogen + ketone systems, Trans. Faraday Soc., 1965, 61, 1618-1625. [all data]

Thermodynamics Research Center, 1997
Thermodynamics Research Center, Selected Values of Properties of Chemical Compounds., Thermodynamics Research Center, Texas A&M University, College Station, Texas, 1997. [all data]

Rodionov P.P., 1969
Rodionov P.P., Thermodynamic functions of 2-butanol (d,l), Izv. Vyssh. Ucheb. Zaved., Khim. Khim. Tekhnol., 1969, 12, 1214-1218. [all data]

Stromsoe E., 1970
Stromsoe E., Heat capacity of alcohol vapors at atmospheric pressure, J. Chem. Eng. Data, 1970, 15, 286-290. [all data]

Berman N.S., 1962
Berman N.S., Thermodynamic properties of 2-butanol, J. Phys. Chem., 1962, 66, 1444-1448. [all data]

Rossini, 1934
Rossini, F.D., Heats of combustion and of formation of the normal aliphatic alcohols in the gaseous and liquid states, and the energies of their atomic linkages, J. Res. NBS, 1934, 13, 189-197. [all data]

Andon, Connett, et al., 1971
Andon, R.J.; Connett, J.E.; Counsell, J.F.; Lees, E.B.; Martin, J.F., Thermodynamic properties of organic oxygen compounds. Part XXVII. (±)-Butan-2-ol and (+)-Butan-2-ol, 1971, J. [all data]

Okano, Ogawa, et al., 1988
Okano, T.; Ogawa, H.; Murakami, S., Molar excess volumes, isentropic compressions, and isobaric heat capacities of methanol-isomeric butanol systems at 298.15 K, Can. J. Chem., 1988, 66, 713-717. [all data]

Piekarski and Somsen, 1988
Piekarski, H.; Somsen, G., Heat capacities and volumes of mixtures of N,N-dimethylformamide with isobutanol, sec-butanol and t-pentanol, J. Chem. Soc., Faraday Trans. 1, 1988, 84(2), 529-537. [all data]

Conti, Gianni, et al., 1976
Conti, G.; Gianni, P.; Matteoli, E.; Mengheri, M., Capacita termiche molari di alcuni composti organici mono- e bifunzionali nel liquido puro e in soluzione acquosa a 25C, Chim. Ind. (Milan), 1976, 58, 225. [all data]

Parks, Thomas, et al., 1936
Parks, G.S.; Thomas, S.B.; Light, D.W., XII. Some new heat capacity data for organic glasses. The entropy and free energy of DL-lactic acid, J. Chem. Phys., 1936, 4, 64-69. [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]

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]

Holmes, Burgers, et al., 1982
Holmes, J.L.; Burgers, P.C.; Mollah, Y.A., Alkane elimination from ionized alkanols, Org. Mass Spectrom., 1982, 17, 127. [all data]

Holmes, Fingas, et al., 1981
Holmes, J.L.; Fingas, M.; Lossing, F.P., Towards a general scheme for estimating the heats of formation of organic ions in the gas phase. Part I. Odd-electron cations, Can. J. Chem., 1981, 59, 80. [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]

Burgers and Holmes, 1982
Burgers, P.C.; Holmes, J.L., Metastable ion studies. XIII. The measurement of appearance energies of metastable peaks, Org. Mass Spectrom., 1982, 17, 123. [all data]

Holmes, Rye, et al., 1979
Holmes, J.L.; Rye, R.T.B.; Terlouw, J.K., On the loss of ethylene from [C₃H₇O]⁺ ions of structure CH₃CH₂CHOH, Org. Mass Spectrom., 1979, 14, 606. [all data]

Harrison, Ivko, et al., 1966
Harrison, A.G.; Ivko, A.; Van Raalte, D., Energetics of formation of some oxygenated ions and the proton affinities of carbonyl compounds, Can. J. Chem., 1966, 44, 1625. [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, 1977
Lossing, F.P., Heats of formation of some isomeric [C_nH_2n+1]⁺ ions. Substitutional effects on ion stability, J. Am. Chem. Soc., 1977, 99, 7526. [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]

Taft, 1987
Taft, R.W., The Nature and Analysis of Substitutent Electronic Effects, Personal communication. See also Prog. Phys. Org. Chem., 1987, 16, 1. [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 thermochemistry data, Condensed phase thermochemistry data, Gas phase ion energetics data, References

Symbols used in this document:

AE	Appearance energy
C_p,gas	Constant pressure heat capacity of gas
C_p,liquid	Constant pressure heat capacity of liquid
IE (evaluated)	Recommended ionization energy
S°_gas	Entropy of gas at standard conditions
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
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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