Cyclohexanone, 2-methyl-
- Formula: C7H12O
- Molecular weight: 112.1696
- IUPAC Standard InChIKey: LFSAPCRASZRSKS-UHFFFAOYSA-N
- CAS Registry Number: 583-60-8
- 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:
- Other names: α-Methylcyclohexanone; 2-Methyl-1-cyclohexanone; 2-Methylcyclohexanone; o-Methylcyclohexanone; 2-Methyl-cyclohexanon; 2-Metilcicloesanone
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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 by: Eugene S. Domalski and Elizabeth D. Hearing
Constant pressure heat capacity of liquid
Cp,liquid (cal/mol*K) | Temperature (K) | Reference |
---|---|---|
48.90 | 290. | Herz and Bloch, 1924 |
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:
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
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tboil | 391.65 | K | N/A | CruzBurguet, Monton, et al., 1993 | Uncertainty assigned by TRC = 0.25 K; TRC |
Tboil | 435.7 | K | N/A | Aldrich Chemical Company Inc., 1990 | BS |
Tboil | 438.2 | K | N/A | White and Bishop, 1940 | Uncertainty assigned by TRC = 0.5 K; TRC |
Tboil | 373.4 | K | N/A | Cowan, Jeffery, et al., 1939 | Uncertainty assigned by TRC = 0.8 K; TRC |
Tboil | 439. | K | N/A | Zelinskii, 1897 | Uncertainty assigned by TRC = 6. K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 264.00 | K | N/A | Plate, Liberman, et al., 1953 | Uncertainty assigned by TRC = 2. K; TRC |
Tfus | 259.25 | K | N/A | Timmermans, 1952 | Uncertainty assigned by TRC = 0.4 K; TRC |
Tfus | 256. | K | N/A | White and Bishop, 1940 | Uncertainty assigned by TRC = 6. K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 10.5 | kcal/mol | EB | Palczewska-Tulinska and Oracz, 2006 | Based on data from 339. to 437. K.; AC |
Enthalpy of vaporization
ΔvapH (kcal/mol) | Temperature (K) | Reference | Comment |
---|---|---|---|
10.8 | 346. | Cruz Burguet, Monton, et al., 1993 | Based on data from 331. to 437. K.; AC |
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 by: 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
By formula: C7H14O = H2 + C7H12O
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 14.9 ± 0.55 | kcal/mol | Eqk | Fedoseenko, Yursha, et al., 1983 | gas phase; At 493 K |
By formula: C7H14O = H2 + C7H12O
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 15.9 ± 0.57 | kcal/mol | Eqk | Fedoseenko, Yursha, et al., 1983 | gas phase; At 493 K |
By formula: H2 + C7H12O = C7H14O
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -15.86 | kcal/mol | Chyd | Dokuchaeva, Sibarov, et al., 1981 | liquid phase |
Gas phase ion energetics 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:
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
B - John E. Bartmess
View reactions leading to C7H12O+ (ion structure unspecified)
Electron affinity determinations
EA (eV) | Reference | Comment |
---|---|---|
0.004207 ± 0.000087 | Hammer, Diri, et al., 2003 | B |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
9.05 | PE | Loudet, Grimaud, et al., 1976 | LLK |
9.5 ± 0.2 | EI | Fortin, Forest, et al., 1973 | LLK |
IR Spectrum
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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
Gas Phase Spectrum
Notice: This spectrum may be better viewed with a Javascript and HTML 5 enabled browser.
Notice: Concentration information is not available for this spectrum and, therefore, molar absorptivity values cannot be derived.
Additional Data
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Download spectrum in JCAMP-DX format.
Owner | NIST Standard Reference Data Program Collection (C) 2018 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 |
State | gas |
Instrument | HP-GC/MS/IRD |
References
Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Herz and Bloch, 1924
Herz, W.; Bloch, W.,
Physikalisch-chemische Untersuchungen an Verbindungen der Cyklohexanreihe,
Z. Phys. Chem., 1924, 110, 23-39. [all data]
CruzBurguet, Monton, et al., 1993
CruzBurguet, M.; Monton, J.B.; Sancho-Tello, M.; Vazquez, M.I.,
Vapor-liquid equilibria of cyclohexanone + cyclohexanol and cyclohexanone + 2-methylcyclohexanone systems at 4.00 and 26.66 kPa,
J. Chem. Eng. Data, 1993, 38, 328-31. [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]
White and Bishop, 1940
White, A.H.; Bishop, W.S.,
Dielectric Evidence of Molecular Rotation in the Crystals of Certain Non-aromatic Compounds,
J. Am. Chem. Soc., 1940, 62, 8-16. [all data]
Cowan, Jeffery, et al., 1939
Cowan, D.M.; Jeffery, G.H.; Vogel, A.I.,
Physical properties and chemical constitution. Part 4. Methylcyclohexane and the multiplanar structure of the methylcyclohexane ring.,
J. Chem. Soc., 1939, 1939, 1862-5. [all data]
Zelinskii, 1897
Zelinskii, N.D.,
Experiments in the Hexamethylene Series,
Ber. Dtsch. Chem. Ges., 1897, 30, 387-91. [all data]
Plate, Liberman, et al., 1953
Plate, A.F.; Liberman, A.L.; Momma, N.A.,
Preparation of 1,2-Dialkylcycloanes. Synthesis of Stereoisomeric 1-Methyl-2-butylcyclopentanes,
Izv. Akad. Nauk SSSR, 1953, 1953, 689. [all data]
Timmermans, 1952
Timmermans, J.,
Freezing points of organic compounds. VVI New determinations.,
Bull. Soc. Chim. Belg., 1952, 61, 393. [all data]
Palczewska-Tulinska and Oracz, 2006
Palczewska-Tulinska, Marcela; Oracz, Pawel,
Vapor Pressures of Hexanal, 2-Methylcyclohexanone, and 2-Cyclohexen-1-one,
J. Chem. Eng. Data, 2006, 51, 2, 639-641, https://doi.org/10.1021/je0504358
. [all data]
Cruz Burguet, Monton, et al., 1993
Cruz Burguet, M.; Monton, Juan B.; Sanchotello, Margarita; Vazquez, M. Isabel,
Vapor-liquid equilibria of cyclohexanone + cyclohexanol and cyclohexanone + 2-methylcyclohexanone systems at 4.00 and 26.66 kPa,
J. Chem. Eng. Data, 1993, 38, 2, 328-331, https://doi.org/10.1021/je00010a037
. [all data]
Fedoseenko, Yursha, et al., 1983
Fedoseenko, V.I.; Yursha, I.A.; Kabo, G.Ya.,
Equilibrium and thermodynamics of cyclohexanol dehydrogenation reactions,
Dokl. Akad. Nauk BSSR, 1983, 27, 926-929. [all data]
Dokuchaeva, Sibarov, et al., 1981
Dokuchaeva, T.G.; Sibarov, d.A.; Timofeev, V.F.; Proskuryakov, V.A.,
Kinetics of the dehydrogenation of 2-methylcyclohexanol to 2-methylcyclohexanone over a platinum catalyst,
J. Appl. Chem. USSR, 1981, 54, 1140-1146. [all data]
Hammer, Diri, et al., 2003
Hammer, N.I.; Diri, K.; Jordan, K.D.; Desfrancois, C.; Compton, R.N.,
Dipole-bound anions of carbonyl, nitrile, and sulfoxide containing molecules,
J. Chem. Phys., 2003, 119, 7, 3650-3660, https://doi.org/10.1063/1.1590959
. [all data]
Loudet, Grimaud, et al., 1976
Loudet, M.; Grimaud, M.; Metras, F.; Pfister-Guillouzo, G.,
Interactions intramoleculaires en serie cyclohexanique partie II. Spectres photoelectroniques de chloro-2-cyclohexanones,
J. Mol. Struct., 1976, 35, 213. [all data]
Fortin, Forest, et al., 1973
Fortin, C.J.; Forest, M.; Vaziri, C.; Gravel, D.; Rousseau, Y.,
Spectrometrie de masse des cyclohexanones gem-diphenylees. I. Localisation de la charge positive,
Can. J. Chem., 1973, 51, 3445. [all data]
Notes
Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, References
- Symbols used in this document:
Cp,liquid Constant pressure heat capacity of liquid EA Electron affinity Tboil Boiling point Tfus Fusion (melting) point ΔrH° Enthalpy of reaction at standard conditions ΔvapH Enthalpy of vaporization ΔvapH° Enthalpy of vaporization at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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