Cyclohexene, 1-methyl-
- Formula: C7H12
- Molecular weight: 96.1702
- IUPAC Standard InChIKey: CTMHWPIWNRWQEG-UHFFFAOYSA-N
- CAS Registry Number: 591-49-1
- 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: α-Methylcyclohexene; 1-Methylcyclohexene; 1-Methyl-1-cyclohexene; 1-Methylcyclohex-1-ene; 1-Methylcyclohexene-1
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Gas phase thermochemistry data
Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, IR Spectrum, 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 | -19.42 ± 0.19 | kcal/mol | Ccb | Labbauf and Rossini, 1961 |
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: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔcH°liquid | -1048.85 ± 0.16 | kcal/mol | Ccb | Labbauf and Rossini, 1961 | Corresponding ΔfHºliquid = -19.40 kcal/mol (simple calculation by NIST; no Washburn corrections) |
ΔcH°liquid | -1047.3 | kcal/mol | Ccb | Zubova, 1901 | Corresponding ΔfHºliquid = -20.9 kcal/mol (simple calculation by NIST; no Washburn corrections) |
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
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tboil | 382. ± 4. | K | AVG | N/A | Average of 21 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 152.71 | K | N/A | Streiff, Schultz, et al., 1957 | Uncertainty assigned by TRC = 0.04 K; TRC |
Tfus | 152.75 | K | N/A | Streiff, Schultz, et al., 1957 | Uncertainty assigned by TRC = 0.03 K; TRC |
Tfus | 152.700 | K | N/A | Streiff, Schultz, et al., 1957 | Uncertainty assigned by TRC = 0.05 K; TRC |
Tfus | 152.2 | K | N/A | Boord, Henne, et al., 1949 | Uncertainty assigned by TRC = 0.5 K; TRC |
Tfus | 152.15 | K | N/A | Anonymous, 1943 | Uncertainty assigned by TRC = 1. K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 8.96 ± 0.05 | kcal/mol | GS | Verevkin, Wandschneider, et al., 2000 | Based on data from 275. to 313. K.; AC |
ΔvapH° | 9.04 | kcal/mol | V | Camin and Rossini, 1960 | ALS |
Enthalpy of vaporization
ΔvapH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
9.01 ± 0.05 | 294. | GS | Verevkin, Wandschneider, et al., 2000 | Based on data from 275. to 313. K.; AC |
8.53 | 348. | A | Stephenson and Malanowski, 1987 | Based on data from 333. to 384. K. See also Eisen and Orav, 1970 and Boublik, Fried, et al., 1984.; AC |
8.77 | 324. | MM | Camin and Rossini, 1960, 2 | Based on data from 309. to 384. 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: H2 + C7H12 = C7H14
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -26.63 ± 0.088 | kcal/mol | Chyd | Rogers, Crooks, et al., 1987 | liquid phase |
ΔrH° | -25.41 ± 0.11 | kcal/mol | Chyd | Turner and Garner, 1958 | liquid phase; solvent: Acetic acid |
ΔrH° | -25.41 ± 0.11 | kcal/mol | Chyd | Turner and Garner, 1957 | liquid phase; solvent: Acetic acid |
By formula: C7H12 + C2HF3O2 = C9H13F3O3
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -8.74 ± 0.21 | kcal/mol | Cac | Wiberg, Wasserman, et al., 1985 | liquid phase; solvent: Trifluoroacetic acid; Trifluoroacetolysis |
By formula: C7H12 + HCl = C7H13Cl
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -13.41 ± 0.21 | kcal/mol | Cm | Arnett and Pienta, 1980 | liquid phase; solvent: Methylene chloride; Hydrochlorination |
By formula: C7H12 = C7H12
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -1.71 ± 0.07 | kcal/mol | Eqk | Yursha, Kabo, et al., 1974 | gas phase; Heat of isomerization at 463 K |
By formula: C7H12 = C7H12
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -1.93 ± 0.07 | kcal/mol | Eqk | Yursha, Kabo, et al., 1974 | gas phase; Heat of isomerization at 463 K |
By formula: C7H12 = C7H12
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -1.39 ± 0.07 | kcal/mol | Eqk | Yursha, Kabo, et al., 1974 | gas phase; Heat of isomerization at 463 K |
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
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Additional Data
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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 | Sadtler Research Labs Under US-EPA Contract |
State | gas |
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 | Japan AIST/NIMC Database- Spectrum MS-NW-9258 |
NIST MS number | 231491 |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, IR Spectrum, 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.
Labbauf and Rossini, 1961
Labbauf, A.; Rossini, F.D.,
Heats of combustion, formation, and hydrogenation of 14 selected cyclomonoolefin hydrocarbons,
J. Phys. Chem., 1961, 65, 476-480. [all data]
Zubova, 1901
Zubova, P.,
Data about heat of combustion of compound cycle structure,
Zh. Fiz. Khim., 1901, 33, 708-722. [all data]
Streiff, Schultz, et al., 1957
Streiff, A.J.; Schultz, L.H.; Hulme, A.R.; Tucker, J.A.; Krouskop, N.C.; Rossini, F.D.,
Purification, Purity, and Freezing Points of 20 API Standard API Research Hydrocarbons,
Anal. Chem., 1957, 29, 361. [all data]
Boord, Henne, et al., 1949
Boord, C.E.; Henne, A.L.; Greenlee, K.W.; Perilstein, W.L.; Derfer, J.M.,
The Grignard Reagent in hydrocarbon synthesis,
Ind. Eng. Chem., 1949, 41, 609. [all data]
Anonymous, 1943
Anonymous, R.,
, Sunbury Rep. No. 2176, Anglo-Iranian Oil Co., 1943. [all data]
Verevkin, Wandschneider, et al., 2000
Verevkin, Sergey P.; Wandschneider, Dirk; Heintz, Andreas,
Determination of Vaporization Enthalpies of Selected Linear and Branched C 7 , C 8 , C 9 , C 11 , and C 12 Monoolefin Hydrocarbons from Transpiration and Correlation Gas-Chromatography Methods,
J. Chem. Eng. Data, 2000, 45, 4, 618-625, https://doi.org/10.1021/je990297k
. [all data]
Camin and Rossini, 1960
Camin, D.L.; Rossini, F.D.,
Physical properties of to selected C7 and C8 alkene hydrocarbons,
J. Chem. Eng. Data, 1960, 5, 368. [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]
Eisen and Orav, 1970
Eisen, O.; Orav, A.,
Eesti NSV Tead. Akad. Toim. Keem. Geol., 1970, 19, 3, 202. [all data]
Boublik, Fried, et al., 1984
Boublik, T.; Fried, V.; Hala, E.,
The Vapour Pressures of Pure Substances: Selected Values of the Temperature Dependence of the Vapour Pressures of Some Pure Substances in the Normal and Low Pressure Region, 2nd ed., Elsevier, New York, 1984, 972. [all data]
Camin and Rossini, 1960, 2
Camin, D.L.; Rossini, F.D.,
Physical Properties of 16 Selected C 7 and C 8 Alkene Hydrocarbons.,
J. Chem. Eng. Data, 1960, 5, 3, 368-372, https://doi.org/10.1021/je60007a037
. [all data]
Rogers, Crooks, et al., 1987
Rogers, D.W.; Crooks, E.; Dejroongruang, K.,
Enthalpies of hydrogenation of the hexenes,
J. Chem. Thermodyn., 1987, 19, 1209-1215. [all data]
Turner and Garner, 1958
Turner, R.B.; Garner, R.H.,
Heats of hydrogenation. V. Relative stabilities in certain exocyclic-endocyclic olefin pairs,
J. Am. Chem. Soc., 1958, 80, 1424-1430. [all data]
Turner and Garner, 1957
Turner, R.B.; Garner, R.H.,
Heats of hydrogenation. V. Relative stabilities in certain exocyclic-endocyclic olefin pairs,
J. Am. Chem. Soc., 1957, 80, 1424-1430. [all data]
Wiberg, Wasserman, et al., 1985
Wiberg, K.B.; Wasserman, D.J.; Martin, E.J.; Murcko, M.A.,
Enthalpies of hydration of alkenes. 3. Cycloalkenes,
J. Am. Chem. Soc., 1985, 107, 6019-6022. [all data]
Arnett and Pienta, 1980
Arnett, E.M.; Pienta, N.J.,
Stabilities of carbonium ions in solution. 12. Heats of formation of alkyl chlorides as an entree to heats of solvation of aliphatic carbonium ions,
J. Am. Chem. Soc., 1980, 102, 3329-3334. [all data]
Yursha, Kabo, et al., 1974
Yursha, I.A.; Kabo, G.Ya.; Andreevskii, D.N.,
Equilibriums and thermodynamics of the isomerization of methylcyclohexenes,
Neftekhimiya, 1974, 14, 688-693. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, IR Spectrum, Mass spectrum (electron ionization), References
- Symbols used in this document:
Tboil Boiling point Tfus Fusion (melting) point ΔcH°liquid Enthalpy of combustion of liquid at standard conditions ΔfH°gas Enthalpy of formation of gas at standard conditions 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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