Cyclohexanol, 2-methyl-, cis-
- Formula: C7H14O
- Molecular weight: 114.1855
- IUPAC Standard InChI: InChI=1S/C7H14O/c1-6-4-2-3-5-7(6)8/h6-8H,2-5H2,1H3/t6-,7+/m1/s1
- IUPAC Standard InChIKey: NDVWOBYBJYUSMF-RQJHMYQMSA-N
- CAS Registry Number: 7443-70-1
- 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. - Stereoisomers:
- Other names: cis-2-Methylcyclohexanol; 2-Methyl-cyclohexanol
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Gas 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 |
|---|---|---|---|---|---|
| ΔfH°gas | -300.7 | kJ/mol | Ccb | Vilcu, Perisanu, et al., 1975 |
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 |
|---|---|---|---|---|---|
| ΔfH°liquid | -362.5 ± 1.9 | kJ/mol | Ccb | Vilcu and Perisanu, 1979 | |
| ΔfH°liquid | -395.7 | kJ/mol | Ccb | Skita and Faust, 1931 | Authors' ΔU=-9127.9±4 cal/g |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔcH°liquid | -4393.0 ± 2.7 | kJ/mol | Ccb | Vilcu and Perisanu, 1979 | Corresponding ΔfHºliquid = -362.4 kJ/mol (simple calculation by NIST; no Washburn corrections) |
| ΔcH°liquid | -4360.6 ± 1.9 | kJ/mol | Ccb | Eliel and Haber, 1958 | Corresponding ΔfHºliquid = -394.7 kJ/mol (simple calculation by NIST; no Washburn corrections) |
| ΔcH°liquid | -4359.7 ± 1.9 | kJ/mol | Ccb | Skita and Faust, 1931 | Authors' ΔU=-9127.9±4 cal/g; Corresponding ΔfHºliquid = -395.7 kJ/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
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| Tboil | 438.2 | K | N/A | Aldrich Chemical Company Inc., 1990 | BS |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔvapH° | 61.76 | kJ/mol | V | Vilcu, Perisanu, et al., 1975 | ALS |
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
C7H13O- + =
By formula: C7H13O- + H+ = C7H14O
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 1554. ± 8.4 | kJ/mol | CIDC | Haas and Harrison, 1993 | gas phase; Both metastable and 50 eV collision energy.; B |
| ΔrH° | 1551. ± 9.2 | kJ/mol | G+TS | Majumdar, Clairet, et al., 1992 | gas phase; Acidity adjusted to 1987 acidity scale; B |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrG° | 1527. ± 8.8 | kJ/mol | H-TS | Haas and Harrison, 1993 | gas phase; Both metastable and 50 eV collision energy.; B |
| ΔrG° | 1523. ± 8.8 | kJ/mol | CIDC | Majumdar, Clairet, et al., 1992 | gas phase; Acidity adjusted to 1987 acidity scale; B |
=
By formula: C7H14O = C7H14O
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 3.9 ± 0.6 | kJ/mol | Eqk | Kabo and Frenkel, 1983 | gas phase; ALS |
| ΔrH° | 3.9 ± 0.6 | kJ/mol | Eqk | Frenkel and Kabo, 1979 | liquid phase; ALS |
=
+
By formula: C7H14O = H2 + C7H12O
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 62.5 ± 2.3 | kJ/mol | Eqk | Fedoseenko, Yursha, et al., 1983 | gas phase; At 493 K; ALS |
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 by: John E. Bartmess
De-protonation reactions
C7H13O- + =
By formula: C7H13O- + H+ = C7H14O
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 1554. ± 8.4 | kJ/mol | CIDC | Haas and Harrison, 1993 | gas phase; Both metastable and 50 eV collision energy. |
| ΔrH° | 1551. ± 9.2 | kJ/mol | G+TS | Majumdar, Clairet, et al., 1992 | gas phase; Acidity adjusted to 1987 acidity scale |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrG° | 1527. ± 8.8 | kJ/mol | H-TS | Haas and Harrison, 1993 | gas phase; Both metastable and 50 eV collision energy. |
| ΔrG° | 1523. ± 8.8 | kJ/mol | CIDC | Majumdar, Clairet, et al., 1992 | gas phase; Acidity adjusted to 1987 acidity scale |
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 | NIST Mass Spectrometry Data Center |
| State | gas |
| Instrument | HP-GC/MS/IRD |
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-IW-1355 |
| NIST MS number | 227877 |
Gas Chromatography
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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
Kovats' RI, non-polar column, isothermal
| Column type | Active phase | Temperature (C) | I | Reference | Comment |
|---|---|---|---|---|---|
| Packed | Apiezon L | 130. | 946. | Paris and Alexandre, 1972 | Chromosorb W AW |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), Gas Chromatography, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Vilcu, Perisanu, et al., 1975
Vilcu, R.; Perisanu, S.; Ciocazanu, I.,
Heats of formation in the ideal gas state of some substances containing carbon, hydrogen and oxygen,
Conf. Int. Thermodyn. Chim. C.R. 4th, 1975, 1, 105-112. [all data]
Vilcu and Perisanu, 1979
Vilcu, R.; Perisanu, S.,
The standard enthalpies of formation of some C, H, O containing compounds,
Rev. Roum. Chim., 1979, 24, 237-243. [all data]
Skita and Faust, 1931
Skita, A.; Faust, W.,
474. Uber die Bildungs-Geschwindigkeiten der stereomeren Methyl-cyclohexanole,
Ber., 1931, 64, 2878-2892. [all data]
Eliel and Haber, 1958
Eliel, E.L.; Haber, R.G.,
The boiling points of the methylcyclohexanols-an exception to the conformational rule,
J. Org. Chem., 1958, 23, 2041. [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]
Haas and Harrison, 1993
Haas, M.J.; Harrison, A.G.,
The Fragmentation of Proton-Bound Cluster Ions and the Gas-Phase Acidities of Alcohols,
Int. J. Mass Spectrom. Ion Proc., 1993, 124, 2, 115, https://doi.org/10.1016/0168-1176(93)80003-W
. [all data]
Majumdar, Clairet, et al., 1992
Majumdar, T.K.; Clairet, F.; Tabet, J.C.; Cooks, R.G.,
PAs of halogenated uridines,
J. Am. Chem . Soc., 1992, 114, 2897. [all data]
Kabo and Frenkel, 1983
Kabo, G.J.; Frenkel, M.L.,
Thermodynamics of diastereomeric transformations of alcohols with different carbon-skeleton structures,
J. Chem. Thermodyn., 1983, 15, 377-381. [all data]
Frenkel and Kabo, 1979
Frenkel, M.L.; Kabo, G.Ya.,
Thermodynamics of stereoisomeric transformations of methylcyclohexanols,
Termodin. Org. Soedin., 1979, 104-106. [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]
Paris and Alexandre, 1972
Paris, C.; Alexandre, P.,
Stereochemical Investigation of Cyclohexane and Terpene Compounds by Gas Chromatography,
J. Chromatogr. Sci., 1972, 10, 6, 402-411, https://doi.org/10.1093/chromsci/10.6.402
. [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, IR Spectrum, Mass spectrum (electron ionization), Gas Chromatography, References
- Symbols used in this document:
Tboil Boiling point ΔcH°liquid Enthalpy of combustion of liquid at standard conditions ΔfH°gas Enthalpy of formation of gas at standard conditions ΔfH°liquid Enthalpy of formation of liquid at standard conditions ΔrG° Free energy of reaction at standard conditions ΔrH° Enthalpy of reaction at standard conditions ΔvapH° Enthalpy of vaporization at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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