Cyclododecanone

Formula: C₁₂H₂₂O
Molecular weight: 182.3025
IUPAC Standard InChI: InChI=1S/C12H22O/c13-12-10-8-6-4-2-1-3-5-7-9-11-12/h1-11H2
IUPAC Standard InChIKey: SXVPOSFURRDKBO-UHFFFAOYSA-N
CAS Registry Number: 830-13-7
Chemical structure:
This structure is also available as a 2d Mol file or as a computed 3d SD file
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NIST / TRC Web Thermo Tables, professional edition (thermophysical and thermochemical data)

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Gas phase thermochemistry data

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Data compiled by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Quantity	Value	Units	Method	Reference	Comment
Δ_fH°_gas	-359.3 ± 3.1	kJ/mol	Ccb	Roux, Jimenez, et al., 1996
Δ_fH°_gas	-349.1 ± 2.3	kJ/mol	Ccb	Wolf, 1972	Hfusion=4.004±0.120 kcal/mol

Condensed phase thermochemistry data

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Data compiled by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Quantity	Value	Units	Method	Reference	Comment
Δ_fH°_solid	-442.5 ± 3.1	kJ/mol	Ccb	Roux, Jimenez, et al., 1996	crystal phase
Δ_fH°_solid	-431.3 ± 2.2	kJ/mol	Ccb	Wolf, 1972	Hfusion=4.004±0.120 kcal/mol
Quantity	Value	Units	Method	Reference	Comment
Δ_cH°_solid	-7436.1 ± 2.6	kJ/mol	Ccb	Roux, Jimenez, et al., 1996	crystal phase; Corresponding Δ_fHº_solid = -430.2 kJ/mol (simple calculation by NIST; no Washburn corrections)
Δ_cH°_solid	-7435.1 ± 2.1	kJ/mol	Ccb	Wolf, 1972	Hfusion=4.004±0.120 kcal/mol; Corresponding Δ_fHº_solid = -431.195 kJ/mol (simple calculation by NIST; no Washburn corrections)

Phase change data

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Data compiled as indicated in comments:
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
BS - Robert L. Brown and Stephen E. Stein
AC - William E. Acree, Jr., James S. Chickos
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Quantity	Value	Units	Method	Reference	Comment
T_boil	538.3	K	N/A	Wolf, 1972, 2	Uncertainty assigned by TRC = 2. K; TRC
Quantity	Value	Units	Method	Reference	Comment
T_fus	335.6	K	N/A	Wolf, 1972, 2	Uncertainty assigned by TRC = 0.1 K; TRC
Quantity	Value	Units	Method	Reference	Comment
Δ_vapH°	65.5 ± 0.6	kJ/mol	N/A	Wolf, 1972	AC
Quantity	Value	Units	Method	Reference	Comment
Δ_subH°	83.2 ± 0.3	kJ/mol	V	Roux, Jimenez, et al., 1996	crystal phase; ALS
Δ_subH°	83.2 ± 0.3	kJ/mol	ME	Roux, Jimenez, et al., 1996	AC

Reduced pressure boiling point

T_boil (K)	Pressure (bar)	Reference	Comment
358.2	0.001	Aldrich Chemical Company Inc., 1990	BS
358.	0.001	Farchan Laboratories, 1990	BS

Enthalpy of vaporization

Δ_vapH (kJ/mol)	Temperature (K)	Method	Reference	Comment
61.	388.	A	Stephenson and Malanowski, 1987	Based on data from 373. to 443. K.; AC
57.9	423.	A,EB	Stephenson and Malanowski, 1987	Based on data from 408. to 450. K. See also Meyer and Hotz, 1976.; AC
54.7	473.	A,EB	Stephenson and Malanowski, 1987	Based on data from 458. to 556. K. See also Meyer and Hotz, 1976.; AC

Enthalpy of fusion

Δ_fusH (kJ/mol)	Temperature (K)	Reference	Comment
16.85	335.6	Roux, Jimenez, et al., 1996	See also Gonthier-Vassal and Szwarc, 1998.; AC

In addition to the Thermodynamics Research Center (TRC) data available from this site, much more physical and chemical property data is available from the following TRC products:

Gas phase ion energetics data

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Data compiled as indicated in comments:
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi

Ionization energy determinations

IE (eV)	Method	Reference	Comment
8.96 ± 0.03	PI	Golubitskii, Kulikov, et al., 1979	LLK

Appearance energy determinations

Ion	AE (eV)	Other Products	Method	Reference	Comment
C₁₀H₁₈O⁺	10.10 ± 0.05	C₂H₄	PI	Golubitskii, Kulikov, et al., 1979	LLK
C₁₂H₂O⁺	10.13 ± 0.05	H₂O	PI	Golubitskii, Kulikov, et al., 1979	LLK
C₁₂H₂₁⁺	10.03 ± 0.05	OH	PI	Golubitskii, Kulikov, et al., 1979	LLK

References

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Roux, Jimenez, et al., 1996
Roux, M.V.; Jimenez, P.; Davalos, J.Z.; Abboud, J.-L.M.; Molina, M.T., Structural effects on the thermochemical properties of cycloalkanones I. Enthalpy of combustion, vapour pressures, and enthalpy of sublimation, and standard enthalpy of formation in the gaseous phas of cyclododecanone, J. Chem. Thermodyn., 1996, 28, 1029-1035. [all data]

Wolf, 1972
Wolf, G., Thermochemische Untersuchungen an cyclischen Ketonen, Helv. Chim. Acta, 1972, 55, 1446-1459. [all data]

Wolf, 1972, 2
Wolf, G., Thermochemical studies of cyclic ketones, Helv. Chim. Acta, 1972, 55, 1446. [all data]

Aldrich Chemical Company Inc., 1990
Aldrich Chemical Company Inc., Catalog Handbook of Fine Chemicals, Aldrich Chemical Company, Inc., Milwaukee WI, 1990, 1. [all data]

Farchan Laboratories, 1990
Farchan Laboratories, Research Chemicals Catalog, Farchan Laboratories, Gainesville, FL, 1990, 91. [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]

Meyer and Hotz, 1976
Meyer, Edwin F.; Hotz, Carol A., Cohesive energies in polar organic liquids. 3. Cyclic ketones, J. Chem. Eng. Data, 1976, 21, 3, 274-279, https://doi.org/10.1021/je60070a035 . [all data]

Gonthier-Vassal and Szwarc, 1998
Gonthier-Vassal, Anne; Szwarc, Henri, Thermodynamic properties of cycloketones: A DSC study, Thermochimica Acta, 1998, 320, 1-2, 141-154, https://doi.org/10.1016/S0040-6031(98)00409-2 . [all data]

Golubitskii, Kulikov, et al., 1979
Golubitskii, A.E.; Kulikov, N.S.; Zyakun, A.M.; Valovoi, V.A.; Alekseev, A.M.; Volkov, V.N., Photoionization mass spectra of alicyclic compounds with various substituents, and their ionization energies and appearance energies, Bull. Acad. Sci. USSR, Div. Chem. Sci., 1979, 11, 2602. [all data]

Notes

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Symbols used in this document:

AE	Appearance energy
T_boil	Boiling point
T_fus	Fusion (melting) point
Δ_cH°_solid	Enthalpy of combustion of solid at standard conditions
Δ_fH°_gas	Enthalpy of formation of gas at standard conditions
Δ_fH°_solid	Enthalpy of formation of solid at standard conditions
Δ_fusH	Enthalpy of fusion
Δ_subH°	Enthalpy of sublimation at standard conditions
Δ_vapH	Enthalpy of vaporization
Δ_vapH°	Enthalpy of vaporization at standard conditions

Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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