Cyclohexane, 1,3-dimethyl-, trans-

Formula: C₈H₁₆
Molecular weight: 112.2126
IUPAC Standard InChI: InChI=1S/C8H16/c1-7-4-3-5-8(2)6-7/h7-8H,3-6H2,1-2H3/t7-,8-/m0/s1
IUPAC Standard InChIKey: SGVUHPSBDNVHKL-YUMQZZPRSA-N
CAS Registry Number: 2207-03-6
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:
- (1R-trans)-1,3-dimethylcyclohexane
Stereoisomers:
- Cyclohexane, 1,3-dimethyl-
- Cyclohexane, 1,3-dimethyl-, cis-
Other names: trans-1,3-Dimethylcyclohexane; 1,trans-3-Dimethylcyclohexane; 1,3-Dimethylcyclohexane, trans; 1,3-Dimethyl(trans)-cyclohexane; Cyclohexane, trans-1,3-dimethyl-; 1,3(trans)-dimethylcyclohexane
Information on this page:
Other data available:
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Data at NIST subscription sites:

NIST / TRC Web Thermo Tables, professional edition (thermophysical and thermochemical data)

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Gas phase thermochemistry data

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Data compiled by: Glushko Thermocenter, Russian Academy of Sciences, Moscow

Quantity	Value	Units	Method	Reference	Comment
S°_gas	89.959	cal/mol*K	N/A	Huffman H.M., 1949

Constant pressure heat capacity of gas

C_p,gas (cal/mol*K)	Temperature (K)	Reference	Comment
9.434	50.	Thermodynamics Research Center, 1997	p=1 bar. There is an appreciable difference, mainly at high temperatures, with values estimated earlier by a method of increments [ Beckett C.W., 1947].
15.44	100.
20.33	150.
24.93	200.
33.37	273.15
36.66	298.15
36.90	300.
50.43	400.
62.69	500.
73.02	600.
81.64	700.
88.89	800.
95.00	900.
100.2	1000.
104.6	1100.
108.3	1200.
111.5	1300.
114.3	1400.
116.6	1500.
121.2	1750.
124.5	2000.
126.8	2250.
128.6	2500.
130.0	2750.
131.0	3000.

Condensed phase thermochemistry data

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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
Δ_cH°_liquid	-1247.38 ± 0.40	kcal/mol	Ccb	Johnson, Prosen, et al., 1947	Corresponding Δ_fHº_liquid = -51.55 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS
Quantity	Value	Units	Method	Reference	Comment
S°_liquid	66.030	cal/mol*K	N/A	Huffman, Todd, et al., 1949	DH

Constant pressure heat capacity of liquid

C_p,liquid (cal/mol*K)	Temperature (K)	Reference	Comment
50.870	298.15	Huffman, Todd, et al., 1949	T = 12 to 310 K.; DH

Phase change data

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Data compiled as indicated in comments:
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
T_boil	396. ± 4.	K	AVG	N/A	Average of 9 values; Individual data points
Quantity	Value	Units	Method	Reference	Comment
T_fus	406.83	K	N/A	Streiff, Murphy, et al., 1947	Uncertainty assigned by TRC = 0.06 K; TRC
T_fus	179.76	K	N/A	Forziati, Glasgow, et al., 1946	Uncertainty assigned by TRC = 0.02 K; called 1,cis-3-cimethylcyclohexane in the article; TRC
T_fus	196.45	K	N/A	Anonymous, 1941	Uncertainty assigned by TRC = 0.5 K; TRC
Quantity	Value	Units	Method	Reference	Comment
T_triple	183.06	K	N/A	Huffman, Todd, et al., 1949, 2	Uncertainty assigned by TRC = 0.02 K; TRC
T_triple	183.030	K	N/A	Huffman, 1948	Uncertainty assigned by TRC = 0.05 K; TRC
T_triple	183.060	K	N/A	Huffman, 1948	Uncertainty assigned by TRC = 0.02 K; TRC
Quantity	Value	Units	Method	Reference	Comment
Δ_vapH°	9.371	kcal/mol	N/A	Majer and Svoboda, 1985
Δ_vapH°	9.35	kcal/mol	N/A	Kusano and Saito, 1975	AC
Δ_vapH°	9.37	kcal/mol	N/A	Reid, 1972	AC
Δ_vapH°	9.37 ± 0.02	kcal/mol	C	Osborne and Ginnings, 1947	AC
Δ_vapH°	9.367	kcal/mol	C	Osborne and Ginnings, 1947, 2	ALS

Enthalpy of vaporization

Δ_vapH (kcal/mol)	Temperature (K)	Method	Reference	Comment
7.980	397.6	N/A	Majer and Svoboda, 1985
9.06	329.	A	Stephenson and Malanowski, 1987	Based on data from 314. to 400. K.; AC
8.94	329.	MM	Willingham, Taylor, et al., 1945	Based on data from 314. to 394. K.; AC

Enthalpy of fusion

Δ_fusH (kcal/mol)	Temperature (K)	Reference	Comment
2.3580	183.06	Huffman, Todd, et al., 1949	DH
2.36	183.1	Domalski and Hearing, 1996	AC

Entropy of fusion

Δ_fusS (cal/mol*K)	Temperature (K)	Reference	Comment
12.88	183.06	Huffman, Todd, et al., 1949	DH

In addition to the Thermodynamics Research Center (TRC) data available from this site, much more physical and chemical property data is available from the following TRC products:

Reaction thermochemistry data

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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

= Cyclohexane, 1,3-dimethyl-, trans-

By formula: C₈H₁₆ = C₈H₁₆

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	-1.9 ± 0.1	kcal/mol	Eqk	Mann, 1968	gas phase; At 593K

Gas phase ion energetics data

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Data evaluated as indicated in comments:
L - Sharon G. Lias

Data compiled as indicated in comments:
LL - Sharon G. Lias and Joel F. Liebman
LBLHLM - Sharon G. Lias, John E. Bartmess, Joel F. Liebman, John L. Holmes, Rhoda D. Levin, and W. Gary Mallard
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi

Quantity	Value	Units	Method	Reference	Comment
IE (evaluated)	9.53	eV	N/A	N/A	L

Ionization energy determinations

IE (eV)	Method	Reference	Comment
9.52 ± 0.05	EI	Holmes and Lossing, 1991	LL
9.53	EQ	Sieck and Mautner(Meot-Ner), 1982	LBLHLM
9.89 ± 0.05	EI	Herzschuh and Sicker, 1981	LLK

Appearance energy determinations

Ion	AE (eV)	Other Products	Method	Reference	Comment
C₆H₁₁⁺	11.05 ± 0.05	C₂H₅	EI	Herzschuh and Sicker, 1981	LLK
C₇H₁₃⁺	10.82 ± 0.05	CH₃	EI	Herzschuh and Sicker, 1981	LLK

References

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Huffman H.M., 1949
Huffman H.M., Low-temperature thermal data on eight C8H16 alkylcyclohexanes, J. Am. Chem. Soc., 1949, 71, 584-592. [all data]

Thermodynamics Research Center, 1997
Thermodynamics Research Center, Selected Values of Properties of Chemical Compounds., Thermodynamics Research Center, Texas A&M University, College Station, Texas, 1997. [all data]

Beckett C.W., 1947
Beckett C.W., The thermodynamic properties and molecular structure of cyclohexane, methylcyclohexane, ethylcyclohexane, and seven dimethylcyclohexanes, J. Am. Chem. Soc., 1947, 69, 2488-2495. [all data]

Johnson, Prosen, et al., 1947
Johnson, W.H.; Prosen, E.J.; Rossini, F.D., Heats of combustion and isomerization of the eight C₈H₁₆ alkylcyclohexanes, J. Res. NBS, 1947, 39, 49-52. [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, 584-592. [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]

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, 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. [all data]

Huffman, 1948
Huffman, H.M., Personal Commun., U. S. Bur. Mines, Bartlesville, OK, 1948. [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]

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]

Mann, 1968
Mann, G., Conformation and physical data of alkanes and cyclanes. IV. Conformation energy of gauche-anticonformers, Tetrahedron, 1968, 24, 6495-65. [all data]

Holmes and Lossing, 1991
Holmes, J.L.; Lossing, F.P., Ionization energies of homologous organic compounds and correlation with molecular size, Org. Mass Spectrom., 1991, 26, 537. [all data]

Sieck and Mautner(Meot-Ner), 1982
Sieck, L.W.; Mautner(Meot-Ner), M., Ionization energies and entropies of cycloalkanes. Kinetics of free energy controlled charge-transfer reactions, J. Phys. Chem., 1982, 86, 3646. [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

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Symbols used in this document:

AE	Appearance energy
C_p,gas	Constant pressure heat capacity of gas
C_p,liquid	Constant pressure heat capacity of liquid
IE (evaluated)	Recommended ionization energy
S°_gas	Entropy of gas at standard conditions
S°_liquid	Entropy of liquid at standard conditions
T_boil	Boiling point
T_fus	Fusion (melting) point
T_triple	Triple point temperature
Δ_cH°_liquid	Enthalpy of combustion of liquid at standard conditions
Δ_fusH	Enthalpy of fusion
Δ_fusS	Entropy of fusion
Δ_rH°	Enthalpy of reaction at standard conditions
Δ_vapH	Enthalpy of vaporization
Δ_vapH°	Enthalpy of vaporization at standard conditions

Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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