Cyclohexanethiol
- Formula: C6H12S
- Molecular weight: 116.224
- IUPAC Standard InChIKey: CMKBCTPCXZNQKX-UHFFFAOYSA-N
- CAS Registry Number: 1569-69-3
- 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: Cyclohexyl mercaptan; Cyclohexyl thiol; Cyklohexylmerkaptan; Cyklohexanthiol
- Permanent link for this species. Use this link for bookmarking this species for future reference.
- Information on this page:
- Other data available:
- Options:
Data at NIST subscription sites:
NIST subscription sites provide data under the NIST Standard Reference Data Program, but require an annual fee to access. The purpose of the fee is to recover costs associated with the development of data collections included in such sites. Your institution may already be a subscriber. Follow the links above to find out more about the data in these sites and their terms of usage.
Gas phase thermochemistry data
Go To: Top, Condensed phase thermochemistry data, Phase change data, Mass spectrum (electron ionization), Gas Chromatography, 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 | -22.88 ± 0.19 | kcal/mol | Ccr | Good, 1972 | |
ΔfH°gas | -22.87 | kcal/mol | Ccb | Scott and Crowder, 1967 | Corrected for Sulfer |
Condensed phase thermochemistry data
Go To: Top, Gas phase thermochemistry data, Phase change data, Mass spectrum (electron ionization), Gas Chromatography, 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:
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 |
---|---|---|---|---|---|
ΔfH°liquid | -33.55 ± 0.19 | kcal/mol | Ccr | Good, 1972 | ALS |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°liquid | -1084.52 ± 0.86 | kcal/mol | Ccr | Good, 1972 | Reanalyzed by Pedley, Naylor, et al., 1986, Original value = -1084.45 ± 0.16 kcal/mol; ALS |
Quantity | Value | Units | Method | Reference | Comment |
S°liquid | 61.083 | cal/mol*K | N/A | Messerly and Todd, 1967 | DH |
Constant pressure heat capacity of liquid
Cp,liquid (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
46.040 | 298.15 | Messerly and Todd, 1967 | T = 10 to 370 K.; DH |
Phase change data
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Mass spectrum (electron ionization), Gas Chromatography, 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:
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
DRB - Donald R. Burgess, Jr.
DH - Eugene S. Domalski and Elizabeth D. Hearing
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tboil | 432.2 | K | N/A | Weast and Grasselli, 1989 | BS |
Tboil | 432. | K | N/A | Majer and Svoboda, 1985 | |
Tboil | 431.95 | K | N/A | Lanum and Morris, 1969 | Uncertainty assigned by TRC = 0.2 K; TRC |
Tboil | 427. | K | N/A | Jones and Reid, 1938 | Uncertainty assigned by TRC = 4. K; TRC |
Tboil | 428. | K | N/A | Sabatier and Mailhe, 1910 | Uncertainty assigned by TRC = 3. K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Ttriple | 189.6300 | K | N/A | Messerly, Todd, et al., 1967 | Uncertainty assigned by TRC = 0.005 K; extrapolation of T vs 1/F plot, meas. in adiab. calorimeter; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Tc | 664. | K | N/A | Majer and Svoboda, 1985 | |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 10.65 | kcal/mol | N/A | Majer and Svoboda, 1985 | |
ΔvapH° | 10.7 | kcal/mol | C | Hossenlopp and Scott, 1981 | AC |
ΔvapH° | 10.67 ± 0.05 | kcal/mol | V | Good, 1972 | ALS |
ΔvapH° | 10.7 | kcal/mol | N/A | Good, 1972 | DRB |
ΔvapH° | 10.7 ± 0.02 | kcal/mol | N/A | Good, 1972 | See also Osborn and Douslin, 1966.; AC |
Enthalpy of vaporization
ΔvapH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
8.858 | 432. | N/A | Majer and Svoboda, 1985 | |
9.85 | 370. | A,EB | Stephenson and Malanowski, 1987 | Based on data from 355. to 476. K. See also Osborn and Douslin, 1966 and Dykyj, Svoboda, et al., 1999.; AC |
Enthalpy of vaporization
ΔvapH =
A exp(-βTr) (1 − Tr)β
ΔvapH =
Enthalpy of vaporization (at saturation pressure)
(kcal/mol)
Tr = reduced temperature (T / Tc)
View plot Requires a JavaScript / HTML 5 canvas capable browser.
Temperature (K) | A (kcal/mol) | β | Tc (K) | Reference | Comment |
---|---|---|---|---|---|
384. to 421. | 14.29 | 0.2811 | 664. | Majer and Svoboda, 1985 |
Antoine Equation Parameters
log10(P) = A − (B / (T + C))
P = vapor pressure (atm)
T = temperature (K)
View plot Requires a JavaScript / HTML 5 canvas capable browser.
Temperature (K) | A | B | C | Reference |
---|---|---|---|---|
356.89 to 475.79 | 4.00628 | 1476.958 | -63.293 | Osborn and Douslin, 1966 |
Enthalpy of fusion
ΔfusH (kcal/mol) | Temperature (K) | Reference | Comment |
---|---|---|---|
2.3901 | 189.64 | Messerly and Todd, 1967 | DH |
2.39 | 189.6 | Domalski and Hearing, 1996 | AC |
Entropy of fusion
ΔfusS (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
12.60 | 189.64 | Messerly and Todd, 1967 | DH |
Mass spectrum (electron ionization)
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Gas Chromatography, 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: NIST Mass Spectrometry Data Center, William E. Wallace, director
Spectrum
Notice: This spectrum may be better viewed with a Javascript and HTML 5 enabled browser.
Additional Data
View image of digitized spectrum (can be printed in landscape orientation).
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. |
---|---|
NIST MS number | 1964 |
Gas Chromatography
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change 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: 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 M | 130. | 983. | Garbuzov, Misharina, et al., 1985 | He or N2, Chromosorb W, AW-DMCS; Column length: 2.1 m |
Kovats' RI, non-polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | Apiezon M | 983. | Zhu, Wang, et al., 2007 | Program: not specified |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, 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.
Good, 1972
Good, W.D.,
Enthalpies of combustion of 18 organic sulfur compounds related to petroleum,
J. Chem. Eng. Data, 1972, 17, 158-162. [all data]
Scott and Crowder, 1967
Scott, D.W.; Crowder, G.A.,
Cyclohexanethiol and 2,4-dimethyl-3-thiapentane: Molecular vibrations, conformational analyses, and chemical thermodynamic properties,
J. Chem. Phys., 1967, 46, 1054-1062. [all data]
Pedley, Naylor, et al., 1986
Pedley, J.B.; Naylor, R.D.; Kirby, S.P.,
Thermochemical Data of Organic Compounds, Chapman and Hall, New York, 1986, 1-792. [all data]
Messerly and Todd, 1967
Messerly, J.F.; Todd, S.S.,
and Guthrie, G.B.Jr, Low-temperature thermal properties of cyclohexanethiol and 2,4-dimethyl-3-thiapentane,
J. Chem. Eng. Data, 1967, 12, 426-429. [all data]
Weast and Grasselli, 1989
CRC Handbook of Data on Organic Compounds, 2nd Editon, Weast,R.C and Grasselli, J.G., ed(s)., CRC Press, Inc., Boca Raton, FL, 1989, 1. [all data]
Majer and Svoboda, 1985
Majer, V.; Svoboda, V.,
Enthalpies of Vaporization of Organic Compounds: A Critical Review and Data Compilation, Blackwell Scientific Publications, Oxford, 1985, 300. [all data]
Lanum and Morris, 1969
Lanum, W.J.; Morris, J.C.,
Physical Properties of Some Sulfur and Nitrogen Compounds,
J. Chem. Eng. Data, 1969, 14, 93-8. [all data]
Jones and Reid, 1938
Jones, S.O.; Reid, E.E.,
The Addition of Sulfurl, Hydrogen Sulfide and Mercaptans to Unsaturated Hydrocarbons,
J. Am. Chem. Soc., 1938, 60, 2452. [all data]
Sabatier and Mailhe, 1910
Sabatier, P.; Mailhe, A.,
General Methods for Direct Preparation of Thiols by Catalysic Splitting of Alcohols,
C. R. Hebd. Seances Acad. Sci., 1910, 150, 1217. [all data]
Messerly, Todd, et al., 1967
Messerly, J.F.; Todd, S.S.; Guthrie, G.B.,
Low Temperature Thermal Properties of Cyclohexanethiol and 2,4-Dimethyl-3-thiapentane,
J. Chem. Eng. Data, 1967, 12, 426-9. [all data]
Hossenlopp and Scott, 1981
Hossenlopp, I.A.; Scott, D.W.,
Vapor heat capacities and enthalpies of vaporizaiton of six organic compounds,
J. Chem. Thermodyn., 1981, 13, 405-414. [all data]
Osborn and Douslin, 1966
Osborn, A.G.; Douslin, D.R.,
Vapor Pressure Relations of 36 Sulfur Compounds Present in Petroleum.,
J. Chem. Eng. Data, 1966, 11, 4, 502-509, https://doi.org/10.1021/je60031a014
. [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]
Dykyj, Svoboda, et al., 1999
Dykyj, J.; Svoboda, J.; Wilhoit, R.C.; Frenkel, M.L.; Hall, K.R.,
Vapor Pressure of Chemicals: Part A. Vapor Pressure and Antoine Constants for Hydrocarbons and Sulfur, Selenium, Tellurium and Hydrogen Containing Organic Compounds, Springer, Berlin, 1999, 373. [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]
Garbuzov, Misharina, et al., 1985
Garbuzov, V.G.; Misharina, T.A.; Aerov, A.F.; Golovnya, R.V.,
Gas chromatographic retention indices for sulphur(II)-containing organic substances,
J. Anal. Chem. USSR (Engl. Transl.), 1985, 40, 4, 576-586. [all data]
Zhu, Wang, et al., 2007
Zhu, X.H.; Wang, W.; Schramm, K.-W.; Niu, W.,
Prediction of the Kova´ ts Retention Indices of Thiols by Use of Quantum Chemical and Physicochemical Descriptors,
Chromatographia, 2007, 65, 11-12, 719-724, https://doi.org/10.1365/s10337-007-0237-3
. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Mass spectrum (electron ionization), Gas Chromatography, References
- Symbols used in this document:
Cp,liquid Constant pressure heat capacity of liquid S°liquid Entropy of liquid at standard conditions Tboil Boiling point Tc Critical temperature Ttriple Triple point temperature 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 ΔfusH Enthalpy of fusion ΔfusS Entropy of fusion ΔvapH Enthalpy of vaporization ΔvapH° Enthalpy of vaporization at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
- The National Institute of Standards and Technology (NIST) uses its best efforts to deliver a high quality copy of the Database and to verify that the data contained therein have been selected on the basis of sound scientific judgment. However, NIST makes no warranties to that effect, and NIST shall not be liable for any damage that may result from errors or omissions in the Database.
- Customer support for NIST Standard Reference Data products.