Cyclohexane, 1,4-dimethyl-, cis-
- Formula: C8H16
- Molecular weight: 112.2126
- IUPAC Standard InChIKey: QRMPKOFEUHIBNM-OCAPTIKFSA-N
- CAS Registry Number: 624-29-3
- 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. - Stereoisomers:
- Other names: cis-1,4-Dimethylcyclohexane; 1,cis-4-Dimethylcyclohexane; 1,4-Dimethylcyclohexane, cis-; Cyclohexane, cis-1,4-dimethyl-; 1,4(cis)-dimethylcyclohexane
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Phase change data
Go To: Top, Gas phase ion energetics data, 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
DH - Eugene S. Domalski and Elizabeth D. Hearing
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tboil | 397. ± 2. | K | AVG | N/A | Average of 17 out of 18 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 186.5 | K | N/A | Boord, Henne, et al., 1949 | Uncertainty assigned by TRC = 0.5 K; TRC |
Tfus | 185.72 | K | N/A | Streiff, Murphy, et al., 1947 | Uncertainty assigned by TRC = 0.03 K; TRC |
Tfus | 185.46 | K | N/A | Boord, Greenlee, et al., 1946 | Uncertainty assigned by TRC = 0.2 K; TRC |
Tfus | 185.42 | K | N/A | Forziati, Glasgow, et al., 1946 | Uncertainty assigned by TRC = 0.02 K; TRC |
Tfus | 186.45 | K | N/A | Anonymous, 1941 | Uncertainty assigned by TRC = 0.7 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Ttriple | 185.73 | K | N/A | Huffman, Todd, et al., 1949 | Uncertainty assigned by TRC = 0.02 K; TRC |
Ttriple | 185.720 | K | N/A | Huffman, 1946 | Uncertainty assigned by TRC = 0.05 K; TRC |
Ttriple | 195.730 | K | N/A | Huffman, 1946 | Uncertainty assigned by TRC = 0.02 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 39.07 | kJ/mol | N/A | Majer and Svoboda, 1985 | |
ΔvapH° | 39. | kJ/mol | N/A | Kusano and Saito, 1975 | AC |
ΔvapH° | 3900. | kJ/mol | N/A | Reid, 1972 | AC |
ΔvapH° | 39.0 ± 0.1 | kJ/mol | C | Osborne and Ginnings, 1947 | AC |
ΔvapH° | 39.02 | kJ/mol | C | Osborne and Ginnings, 1947, 2 | ALS |
Enthalpy of vaporization
ΔvapH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
33.28 | 397.5 | N/A | Majer and Svoboda, 1985 | |
37.6 | 332. | A,MM | Stephenson and Malanowski, 1987 | Based on data from 317. to 400. K. See also Willingham, Taylor, et al., 1945.; AC |
Enthalpy of fusion
ΔfusH (kJ/mol) | Temperature (K) | Reference | Comment |
---|---|---|---|
9.3069 | 185.73 | Huffman, Todd, et al., 1949, 2 | DH |
9.29 | 185.7 | Domalski and Hearing, 1996 | AC |
Entropy of fusion
ΔfusS (J/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
50.11 | 185.73 | Huffman, Todd, et al., 1949, 2 | DH |
Gas phase ion energetics data
Go To: Top, Phase change data, 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: Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
Ionization energy determinations
IE (eV) | Method | Reference |
---|---|---|
≤9.93 ± 0.05 | EI | Herzschuh and Sicker, 1981 |
Appearance energy determinations
Ion | AE (eV) | Other Products | Method | Reference | Comment |
---|---|---|---|---|---|
C6H11+ | 11.16 ± 0.05 | C2H5 | EI | Herzschuh and Sicker, 1981 | |
C7H13+ | 10.78 ± 0.05 | CH3 | EI | Herzschuh and Sicker, 1981 |
References
Go To: Top, Phase change data, Gas phase ion energetics data, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
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]
Streiff, Murphy, et al., 1947
Streiff, A.J.; Murphy, E.T.; Cahill, J.C.; Flanagan, H.F.; Sedlak, V.A.; Willingham, C.B.; Rossini, F.D.,
Purification, Purity, and Freezing Points of 8 Nonanes, 11 Alkyl- cyclopentanes, 6 Alkylcyclohexanes, and 4 Butylbenzenes of the API-NBS Series,
J. Res. Natl. Bur. Stand. (U. S.), 1947, 38, 53. [all data]
Boord, Greenlee, et al., 1946
Boord, C.E.; Greenlee, K.W.; Perilstein, W.L.,
The Synthesis, Purification and Prop. of Hydrocarbons of Low Mol. Weight, Am. Pet. Inst. Res. Proj. 45, Eighth Annu. Rep., Ohio State Univ., June 30, 1946. [all data]
Forziati, Glasgow, et al., 1946
Forziati, A.F.; Glasgow, A.R.; Willingham, C.B.; Rossini, F.D.,
Specification adn Properties of 29 Paraffin, 4 Alkylcyclopentanes, 10 Alkylcyclohexanes and 8 Alkylbenzene Hydrocarbons,
J. Res. Natl. Bur. Stand. (U. S.), 1946, 36, 129. [all data]
Anonymous, 1941
Anonymous, R.,
, Am. Pet. Inst. Hydrocarbon Res. Proj., Third Annu. Rep., Ohio State Univ., Aug. 31, 1941. [all data]
Huffman, Todd, et al., 1949
Huffman, H.M.; Todd, S.S.; Oliver, G.D.,
Low Temperature Thermal Data on Eight C8H16 Alkylcyclohexanes,
J. Am. Chem. Soc., 1949, 71, 584. [all data]
Huffman, 1946
Huffman, H.M.,
Personal Commun., U. S. Bur. Mines, Bartlesville, OK, 1946. [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]
Kusano and Saito, 1975
Kusano, K.; Saito, Y.,
, Preprints 33rd Ann. Meeting Chem. Soc. Japan, Japan, 1975, 123. [all data]
Reid, 1972
Reid, Robert C.,
Handbook on vapor pressure and heats of vaporization of hydrocarbons and related compounds, R. C. Wilhort and B. J. Zwolinski, Texas A Research Foundation. College Station, Texas(1971). 329 pages.$10.00,
AIChE J., 1972, 18, 6, 1278-1278, https://doi.org/10.1002/aic.690180637
. [all data]
Osborne and Ginnings, 1947
Osborne, Nathan S.; Ginnings, Defoe C.,
Measurements of heat of vaporization and heat capacity of a number of hydrocarbons,
J. RES. NATL. BUR. STAN., 1947, 39, 5, 453-17, https://doi.org/10.6028/jres.039.031
. [all data]
Osborne and Ginnings, 1947, 2
Osborne, N.S.; Ginnings, D.C.,
Measurements of heat of vaporization and heat capacity of a number of hydrocarbons,
J. Res. NBS, 1947, 39, 453-477. [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]
Willingham, Taylor, et al., 1945
Willingham, C.B.; Taylor, W.J.; Pignocco, J.M.; Rossini, F.D.,
Vapor pressures and boiling points of some paraffin, alkylcyclopentane, alkylcyclohexane, and alkylbenzene hydrocarbons,
J. RES. NATL. BUR. STAN., 1945, 35, 3, 219-17, https://doi.org/10.6028/jres.035.009
. [all data]
Huffman, Todd, et al., 1949, 2
Huffman, H.M.; Todd, S.S.; Oliver, G.D.,
Low temperature thermal data on eight C8H16 alkylcyclohexanes,
J. Am. Chem. Soc., 1949, 71, 584-592. [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]
Herzschuh and Sicker, 1981
Herzschuh, R.; Sicker, A.,
Stereochemische einflusse auf die ionisations- und auftrittsenergien cis/trans-isomerer dimethylcycloalkane,
Z. Chem., 1981, 21, 409. [all data]
Notes
Go To: Top, Phase change data, Gas phase ion energetics data, References
- Symbols used in this document:
AE Appearance energy Tboil Boiling point Tfus Fusion (melting) point Ttriple Triple point temperature 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
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