2-Octanone
- Formula: C8H16O
- Molecular weight: 128.2120
- IUPAC Standard InChIKey: ZPVFWPFBNIEHGJ-UHFFFAOYSA-N
- CAS Registry Number: 111-13-7
- 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. - Other names: n-Hexyl methyl ketone; Hexyl methyl ketone; Methyl hexyl ketone; Methyl n-hexyl ketone; Octan-2-one; n-C6H13COCH3; Octanone-2
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Gas phase thermochemistry data
Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Mass spectrum (electron ionization), References, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Data compiled by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°gas | -345.1 ± 2.5 | kJ/mol | Ccr | Geiseler and Ratzsch, 1965 |
Condensed phase 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:
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 |
---|---|---|---|---|---|
ΔcH°liquid | -5050.13 | kJ/mol | Ccr | Geiseler and Ratzsch, 1965 | Corresponding ΔfHºliquid = -384.6 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS |
ΔcH°liquid | -5070.2 | kJ/mol | Ccb | Guinchant, 1918 | Corresponding ΔfHºliquid = -364. kJ/mol (simple calculation by NIST; no Washburn corrections); ALS |
Quantity | Value | Units | Method | Reference | Comment |
S°liquid | 373.84 | J/mol*K | N/A | Oetting, 1965 | DH |
Constant pressure heat capacity of liquid
Cp,liquid (J/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
273.26 | 298.15 | Oetting, 1965 | T = 13 to 330 K.; DH |
274.5 | 298. | von Reis, 1881 | T = 291 to 463 K.; DH |
Phase change 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:
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
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tboil | 446. ± 2. | K | AVG | N/A | Average of 27 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 251.6 | K | N/A | Timmermans, 1922 | Uncertainty assigned by TRC = 0.4 K; TRC |
Tfus | 251.15 | K | N/A | Timmermans and Mattaar, 1921 | Uncertainty assigned by TRC = 0.5 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Ttriple | 252.79 | K | N/A | Oetting, 1965, 2 | Uncertainty assigned by TRC = 0.08 K; TRC |
Ttriple | 252.86 | K | N/A | Oetting, 1965, 2 | Uncertainty assigned by TRC = 0.06 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Tc | 632.7 | K | N/A | Pulliam, Gude, et al., 1994 | Uncertainty assigned by TRC = 0.2 K; by the sealed ampule method; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ρc | 2.01 | mol/l | N/A | Pulliam, Gude, et al., 1994 | Uncertainty assigned by TRC = 0.02 mol/l; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 52.6 | kJ/mol | CGC | Chickos, Hosseini, et al., 1995 | Based on data from 343. to 383. K.; AC |
ΔvapH° | 52.0 ± 0.3 | kJ/mol | GCC | Saluja, Peacock, et al., 1979 | AC |
ΔvapH° | 51.8 | kJ/mol | N/A | Ambrose, Ellender, et al., 1975 | Based on data from 324. to 520. K.; AC |
ΔvapH° | 39.8 ± 0.2 | kJ/mol | V | Geiseler and Ratzsch, 1965 | ALS |
Enthalpy of vaporization
ΔvapH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
49.8 | 332. | A | Stephenson and Malanowski, 1987 | Based on data from 317. to 446. K.; AC |
49.1 | 339. | A | Stephenson and Malanowski, 1987 | Based on data from 324. to 520. K. See also Ambrose, Ellender, et al., 1975.; AC |
50.6 | 311. | N/A | Stull, 1947 | Based on data from 296. to 446. K.; AC |
Antoine Equation Parameters
log10(P) = A − (B / (T + C))
P = vapor pressure (bar)
T = temperature (K)
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Temperature (K) | A | B | C | Reference | Comment |
---|---|---|---|---|---|
296.8 to 446.1 | 4.9448 | 2004.031 | -40.324 | Stull, 1947 | Coefficents calculated by NIST from author's data. |
Enthalpy of fusion
ΔfusH (kJ/mol) | Temperature (K) | Reference | Comment |
---|---|---|---|
24.419 | 252.86 | Oetting, 1965 | DH |
24.42 | 252.9 | Domalski and Hearing, 1996 | AC |
Entropy of fusion
ΔfusS (J/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
96.57 | 252.86 | Oetting, 1965 | DH |
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
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
C8H15O- + =
By formula: C8H15O- + H+ = C8H16O
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 1525. ± 8.8 | kJ/mol | TDEq | Burkell, Fridgen, et al., 2003 | gas phase; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 1496. ± 8.8 | kJ/mol | TDEq | Burkell, Fridgen, et al., 2003 | gas phase; B |
By formula: C8H18O = C8H16O + H2
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 52.97 | kJ/mol | Eqk | Cubberley and Mueller, 1946 | gas phase; ALS |
Gas phase ion energetics data
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Mass spectrum (electron ionization), 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:
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
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
9.75 | EI | Potzinger and Bunau, 1969 | RDSH |
9.40 ± 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+ | 12.04 | ? | EI | Potzinger and Bunau, 1969 | RDSH |
C6H13+ | 10.21 | ? | EI | Potzinger and Bunau, 1969 | RDSH |
C7H13O+ | 9.85 | CH3 | EI | Potzinger and Bunau, 1969 | RDSH |
De-protonation reactions
C8H15O- + =
By formula: C8H15O- + H+ = C8H16O
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 1525. ± 8.8 | kJ/mol | TDEq | Burkell, Fridgen, et al., 2003 | gas phase; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 1496. ± 8.8 | kJ/mol | TDEq | Burkell, Fridgen, et al., 2003 | gas phase; B |
Mass spectrum (electron ionization)
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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 by: NIST Mass Spectrometry Data Center, William E. Wallace, director
Spectrum
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Additional Data
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Due to licensing restrictions, this spectrum cannot be downloaded.
Owner | NIST Mass Spectrometry Data Center Collection (C) 2014 copyright by the U.S. Secretary of Commerce on behalf of the United States of America. All rights reserved. |
---|---|
Origin | NIST Mass Spectrometry Data Center, 1990. |
NIST MS number | 114247 |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Mass spectrum (electron ionization), Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Geiseler and Ratzsch, 1965
Geiseler, V.G.; Ratzsch, M.,
Bildungsenthalpien stellungsisomerer n-Alkanderivate. 1. Mitteilung: Bildungsenthalpien des Octanals und der drei isomeren Octanone,
Ber. Bunsen-Ges. Phys. Chem., 1965, 69, 485-488. [all data]
Guinchant, 1918
Guinchant, M.J.,
Etude sur la fonction acide dans les derives metheniques et methiniques,
Ann. Chem., 1918, 10, 30-84. [all data]
Oetting, 1965
Oetting, F.L.,
Absolute entropies of the methyl alkyl ketones at 298.15 K,
J. Chem. Eng. Data, 1965, 10, 122-125. [all data]
von Reis, 1881
von Reis, M.A.,
Die specifische Wärme flüssiger organischer Verbindungen und ihre Beziehung zu deren Moleculargewicht,
Ann. Physik [3], 1881, 13, 447-464. [all data]
Timmermans, 1922
Timmermans, J.,
Investigation of the Freezing Point of Organic Substances VII,
Bull. Soc. Chim. Belg., 1922, 31, 389. [all data]
Timmermans and Mattaar, 1921
Timmermans, J.; Mattaar, J.F.,
Freezing points of orgainic substances VI. New experimental determinations.,
Bull. Soc. Chim. Belg., 1921, 30, 213. [all data]
Oetting, 1965, 2
Oetting, F.L.,
Absolute Entropies of the Methyl Alkyl Ketones 1t 298.15 K,
J. Chem. Eng. Data, 1965, 10, 122-5. [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]
Chickos, Hosseini, et al., 1995
Chickos, James S.; Hosseini, Sarah; Hesse, Donald G.,
Determination of vaporization enthalpies of simple organic molecules by correlations of changes in gas chromatographic net retention times,
Thermochimica Acta, 1995, 249, 41-62, https://doi.org/10.1016/0040-6031(95)90670-3
. [all data]
Saluja, Peacock, et al., 1979
Saluja, P.P.S.; Peacock, L.A.; Fuchs, R.,
Enthalpies of interaction of aliphatic ketones with polar and nonpolar solvents,
J. Am. Chem. Soc., 1979, 101, 1958-1962. [all data]
Ambrose, Ellender, et al., 1975
Ambrose, D.; Ellender, J.H.; Lees, E.B.; Sprake, C.H.S.; Townsend, R.,
Thermodynamic properties of organic oxygen compounds XXXVIII. Vapour pressures of some aliphatic ketones,
The Journal of Chemical Thermodynamics, 1975, 7, 5, 453-472, https://doi.org/10.1016/0021-9614(75)90275-X
. [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]
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]
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]
Cubberley and Mueller, 1946
Cubberley, A.H.; Mueller, M.B.,
Equilibrium studies on the dehydrogenation of primary and secondary alcohols. I. 2-Butanol, 2-octanol, cyclopentanol and benzyl alcohol,
J. Am. Chem. Soc., 1946, 68, 1149-1151. [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]
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]
Notes
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Mass spectrum (electron ionization), References
- Symbols used in this document:
AE Appearance energy Cp,liquid Constant pressure heat capacity of liquid S°liquid Entropy of liquid at standard conditions Tboil Boiling point Tc Critical temperature Tfus Fusion (melting) point Ttriple Triple point temperature ΔcH°liquid Enthalpy of combustion of liquid at standard conditions ΔfH°gas Enthalpy of formation of gas at standard conditions 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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