2-Hexanone
- Formula: C6H12O
- Molecular weight: 100.1589
- IUPAC Standard InChIKey: QQZOPKMRPOGIEB-UHFFFAOYSA-N
- CAS Registry Number: 591-78-6
- 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. - Isotopologues:
- Other names: n-Butyl methyl ketone; Butyl methyl ketone; Hexan-2-one; Methyl butyl ketone; Methyl n-butyl ketone; 2-Oxohexane; n-C4H9COCH3; Hexanone-2; Ketone, butyl methyl; MBK; MNBK; Propylacetone
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Phase change data
Go To: Top, Gas phase ion energetics data, References, Notes
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:
BS - Robert L. Brown and Stephen E. Stein
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
AC - William E. Acree, Jr., James S. Chickos
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DH - Eugene S. Domalski and Elizabeth D. Hearing
CAL - James S. Chickos, William E. Acree, Jr., Joel F. Liebman, Students of Chem 202 (Introduction to the Literature of Chemistry), University of Missouri -- St. Louis
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tboil | 400. ± 2. | K | AVG | N/A | Average of 35 out of 36 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 216.25 | K | N/A | Timmermans, 1921 | Uncertainty assigned by TRC = 0.3 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Ttriple | 217.69 | K | N/A | Andon, Counsell, et al., 1970 | Uncertainty assigned by TRC = 0.05 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Tc | 586.6 | K | N/A | Pulliam, Gude, et al., 1994 | Uncertainty assigned by TRC = 0.4 K; by the sealed ampule method; TRC |
Tc | 587. | K | N/A | Majer and Svoboda, 1985 | |
Tc | 587.0 | K | N/A | Ambrose, Broderick, et al., 1974 | Uncertainty assigned by TRC = 0.5 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Pc | 33.20 | bar | N/A | Ambrose, Broderick, et al., 1974 | Uncertainty assigned by TRC = 0.80 bar; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ρc | 2.67 | mol/l | N/A | Pulliam, Gude, et al., 1994 | Uncertainty assigned by TRC = 0.03 mol/l; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 42.8 ± 0.7 | kJ/mol | AVG | N/A | Average of 8 values; Individual data points |
Enthalpy of vaporization
ΔvapH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
43.100 | 400.7 | N/A | Svoboda, Kubes, et al., 1992 | Value corrected to 298.15 K.; DH |
36.35 | 400.7 | N/A | Majer and Svoboda, 1985 | |
39.0 | 374. | EB | Siimer, Kirss, et al., 2002 | Based on data from 359. to 401. K.; AC |
42.5 ± 0.1 | 308. | C | Svoboda, Kubes, et al., 1992 | AC |
41.6 ± 0.1 | 323. | C | Svoboda, Kubes, et al., 1992 | AC |
40.7 ± 0.1 | 338. | C | Svoboda, Kubes, et al., 1992 | AC |
40.1 ± 0.1 | 348. | C | Svoboda, Kubes, et al., 1992 | AC |
39.5 ± 0.1 | 358. | C | Svoboda, Kubes, et al., 1992 | AC |
40.8 | 308. | A | Stephenson and Malanowski, 1987 | Based on data from 293. to 411. K.; AC |
43.8 | 294. | A | Stephenson and Malanowski, 1987 | Based on data from 279. to 423. K.; AC |
41.5 | 325. | A | Stephenson and Malanowski, 1987 | Based on data from 310. to 427. K.; AC |
36.7 | 436. | A | Stephenson and Malanowski, 1987 | Based on data from 421. to 523. K.; AC |
36.1 | 528. | A | Stephenson and Malanowski, 1987 | Based on data from 513. to 587. K.; AC |
53.8 | 295. | N/A | Stull, 1947 | Based on data from 280. to 400. K.; AC |
Enthalpy of vaporization
ΔvapH =
A exp(-βTr) (1 − Tr)β
ΔvapH =
Enthalpy of vaporization (at saturation pressure)
(kJ/mol)
Tr = reduced temperature (T / Tc)
View plot Requires a JavaScript / HTML 5 canvas capable browser.
Temperature (K) | A (kJ/mol) | β | Tc (K) | Reference | Comment |
---|---|---|---|---|---|
298. to 368. | 60.61 | 0.2794 | 587. | Majer and Svoboda, 1985 |
Antoine Equation Parameters
log10(P) = A − (B / (T + C))
P = vapor pressure (bar)
T = temperature (K)
View plot Requires a JavaScript / HTML 5 canvas capable browser.
Temperature (K) | A | B | C | Reference | Comment |
---|---|---|---|---|---|
280.9 to 400.7 | 5.66715 | 2011.668 | -45.364 | Stull, 1947 | Coefficents calculated by NIST from author's data. |
Enthalpy of fusion
ΔfusH (kJ/mol) | Temperature (K) | Reference | Comment |
---|---|---|---|
14.900 | 217.69 | Andon, Counsell, et al., 1970, 2 | DH |
14.9 | 217.7 | Domalski and Hearing, 1996 | AC |
Entropy of fusion
ΔfusS (J/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
68.44 | 217.69 | Andon, Counsell, et al., 1970, 2 | DH |
68.42 | 217.7 | Domalski and Hearing, 1996 | CAL |
Gas phase ion energetics data
Go To: Top, Phase change data, References, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Data evaluated as indicated in comments:
L - Sharon G. Lias
Data compiled as indicated in comments:
B - John E. Bartmess
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron
LBLHLM - Sharon G. Lias, John E. Bartmess, Joel F. Liebman, John L. Holmes, Rhoda D. Levin, and W. Gary Mallard
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
IE (evaluated) | 9.35 ± 0.06 | eV | N/A | N/A | L |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
9.24 ± 0.02 | PE | Ashmore and Burgess, 1978 | LLK |
9.331 ± 0.005 | PE | Hernandez, Masclet, et al., 1977 | LLK |
9.2 | EI | McLafferty, Bente, et al., 1973 | LLK |
9.36 ± 0.02 | PE | Cocksey, Eland, et al., 1971 | LLK |
9.37 ± 0.02 | PI | Murad and Inghram, 1964 | RDSH |
9.34 ± 0.03 | PI | Watanabe, Nakayama, et al., 1962 | RDSH |
9.44 ± 0.03 | PI | Vilesov, 1960 | RDSH |
9.38 | PE | Benoit and Harrison, 1977 | Vertical value; LLK |
Appearance energy determinations
Ion | AE (eV) | Other Products | Method | Reference | Comment |
---|---|---|---|---|---|
C2H3O+ | 11.65 | ? | EI | Potzinger and Bunau, 1969 | RDSH |
C2H3O+ | 10.8 | ? | PI | Murad and Inghram, 1964 | RDSH |
C3H6O+ | 10.1 ± 0.1 | C3H6 | EI | Burgers and Holmes, 1982 | LBLHLM |
C3H6O+ | 10.04 | C3H6 | EI | Holmes and Lossing, 1980 | LLK |
C3H6O+ | 10.00 | C3H6 | PI | Murad and Inghram, 1964 | RDSH |
C4H7O+ | 10.03 | C2H5 | PI | Murad and Inghram, 1964 | RDSH |
C4H9+ | 11.92 | ? | EI | Potzinger and Bunau, 1969 | RDSH |
C5H9O+ | 9.4 | CH3 | EI | McLafferty, Bente, et al., 1973 | LLK |
C5H9O+ | 9.66 | CH3 | PI | Murad and Inghram, 1964 | RDSH |
De-protonation reactions
C6H11O- + =
By formula: C6H11O- + H+ = C6H12O
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 1531. ± 8.8 | kJ/mol | TDEq | Burkell, Fridgen, et al., 2003 | gas phase; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 1501. ± 8.4 | kJ/mol | TDEq | Burkell, Fridgen, et al., 2003 | gas phase; B |
References
Go To: Top, Phase change data, Gas phase ion energetics data, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Timmermans, 1921
Timmermans, J.,
The Freezing Points of Organic Substances IV. New Exp. Determinations,
Bull. Soc. Chim. Belg., 1921, 30, 62. [all data]
Andon, Counsell, et al., 1970
Andon, R.J.L.; Counsell, J.F.; Lees, E.B.; Martin, J.F.,
Thermodynamic Properties of Organic Oxygen Compounds Part XXIII. Low- temperature Heat Capacity and Entropy of C6, C7, and C9 Ketones,
J. Chem. Soc. A, 1970, 1970, 833. [all data]
Pulliam, Gude, et al., 1994
Pulliam, M.K.; Gude, M.T.; Teja, A.S.,
The Critical Properties of Twelve Isomeric n-Alkanones with Six to Nine Carbon Atoms,
Experimental Results for DIPPR 1990-91 Projects on Phase Equilibria and Pure Component Properties, 1994, 1994, DIPPR Data Ser. No. 2, p. 184-87. [all data]
Majer and Svoboda, 1985
Majer, V.; Svoboda, V.,
Enthalpies of Vaporization of Organic Compounds: A Critical Review and Data Compilation, Blackwell Scientific Publications, Oxford, 1985, 300. [all data]
Ambrose, Broderick, et al., 1974
Ambrose, D.; Broderick, B.E.; Townsend, R.,
The Critical Temperatures and Pressures of Thirty Organic Compounds,
J. Appl. Chem. Biotechnol., 1974, 24, 359. [all data]
Svoboda, Kubes, et al., 1992
Svoboda, V.; Kubes, V.; Basarova, P.,
Enthalpies of vaporization and cohesive energies of hexan-2-one, 2-methylpentan-4-one, 2,2-dimethylbutan-3-one, 2,6-dimethylheptan-4-one and cyclohexanone,
J. Chem. Thermodynam., 1992, 24, 333-336. [all data]
Siimer, Kirss, et al., 2002
Siimer, E.; Kirss, H.; Kuus, M.; Kudryavtseva, L.,
Proc. Est. Acad. Sci. Chem., 2002, 51, 1, 19. [all data]
Stephenson and Malanowski, 1987
Stephenson, Richard M.; Malanowski, Stanislaw,
Handbook of the Thermodynamics of Organic Compounds, 1987, https://doi.org/10.1007/978-94-009-3173-2
. [all data]
Stull, 1947
Stull, Daniel R.,
Vapor Pressure of Pure Substances. Organic and Inorganic Compounds,
Ind. Eng. Chem., 1947, 39, 4, 517-540, https://doi.org/10.1021/ie50448a022
. [all data]
Andon, Counsell, et al., 1970, 2
Andon, R.J.L.; Counsell, J.F.; Lees, E.B.; Martin, J.F.,
Thermodynamic properties of organic oxygen compounds. Part XXIII. Low-temperature heat capacity and entropy of C6, C7,
and C9 ketones, 1970, J. [all data]
Domalski and Hearing, 1996
Domalski, Eugene S.; Hearing, Elizabeth D.,
Heat Capacities and Entropies of Organic Compounds in the Condensed Phase. Volume III,
J. Phys. Chem. Ref. Data, 1996, 25, 1, 1, https://doi.org/10.1063/1.555985
. [all data]
Ashmore and Burgess, 1978
Ashmore, F.S.; Burgess, A.R.,
Photoelectron spectra of the unbranched C5-C7 alkenes, aldehydes and ketones,
J. Chem. Soc. Faraday Trans. 2, 1978, 74, 734. [all data]
Hernandez, Masclet, et al., 1977
Hernandez, R.; Masclet, P.; Mouvier, G.,
Spectroscopie de photoelectrons d'aldehydes et de cetones aliphatiques,
J. Electron Spectrosc. Relat. Phenom., 1977, 10, 333. [all data]
McLafferty, Bente, et al., 1973
McLafferty, F.W.; Bente, P.F., III; Kornfeld, R.; Tsai, S.-C.; Howe, I.,
Collisional activation spectra of organic ions,
J. Am. Chem. Soc., 1973, 95, 2120. [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]
Murad and Inghram, 1964
Murad, E.; Inghram, M.G.,
Photoionization of aliphatic ketones,
J. Chem. Phys., 1964, 40, 3263. [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]
Vilesov, 1960
Vilesov, F.I.,
The photoionization of vapors of compounds whose molecules contain carbonyl groups,
Dokl. Phys. Chem., 1960, 132, 521, In original 1332. [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]
Potzinger and Bunau, 1969
Potzinger, P.; Bunau, G.v.,
Empirische Beruksichtigung von Uberschussenergien bei der Auftrittspotentialbestimmung,
Ber. Bunsen-Ges. Phys. Chem., 1969, 73, 466. [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 and Lossing, 1980
Holmes, J.L.; Lossing, F.P.,
Gas-phase heats of formation of keto and enol ions of carbonyl compounds.,
J. Am. Chem. Soc., 1980, 102, 1591. [all data]
Burkell, Fridgen, et al., 2003
Burkell, J.L.; Fridgen, T.D.; McMahon, T.B.,
Gas-phase acidities and sites of deprotonation of 2-ketones and structures of the corresponding enolates,
Int. J. Mass Spectrom., 2003, 227, 3, 497-508, https://doi.org/10.1016/S1387-3806(03)00102-7
. [all data]
Notes
Go To: Top, Phase change data, Gas phase ion energetics data, References
- Symbols used in this document:
AE Appearance energy IE (evaluated) Recommended ionization energy Pc Critical pressure Tboil Boiling point Tc Critical temperature Tfus Fusion (melting) point Ttriple Triple point temperature ΔfusH Enthalpy of fusion ΔfusS Entropy of fusion ΔrG° Free energy of reaction at standard conditions ΔrH° Enthalpy of reaction at standard conditions ΔvapH Enthalpy of vaporization ΔvapH° Enthalpy of vaporization at standard conditions ρc Critical density - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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