Cyclohexane, 1,3-dimethyl-, trans-
- Formula: C8H16
- Molecular weight: 112.2126
- 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:
- Stereoisomers:
- 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
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Condensed phase thermochemistry data
Go To: Top, Phase change data, Gas phase ion energetics 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 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 |
---|---|---|---|---|---|
ΔcH°liquid | -1247.38 ± 0.40 | kcal/mol | Ccb | Johnson, Prosen, et al., 1947 | Corresponding ΔfHºliquid = -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
Cp,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 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:
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 | 396. ± 4. | K | AVG | N/A | Average of 9 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 406.83 | K | N/A | Streiff, Murphy, et al., 1947 | Uncertainty assigned by TRC = 0.06 K; TRC |
Tfus | 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 |
Tfus | 196.45 | K | N/A | Anonymous, 1941 | Uncertainty assigned by TRC = 0.5 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Ttriple | 183.06 | K | N/A | Huffman, Todd, et al., 1949, 2 | Uncertainty assigned by TRC = 0.02 K; TRC |
Ttriple | 183.030 | K | N/A | Huffman, 1948 | Uncertainty assigned by TRC = 0.05 K; TRC |
Ttriple | 183.060 | K | N/A | Huffman, 1948 | Uncertainty assigned by TRC = 0.02 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 9.371 | kcal/mol | N/A | Majer and Svoboda, 1985 | |
ΔvapH° | 9.35 | kcal/mol | N/A | Kusano and Saito, 1975 | AC |
ΔvapH° | 9.37 | kcal/mol | N/A | Reid, 1972 | AC |
ΔvapH° | 9.37 ± 0.02 | kcal/mol | C | Osborne and Ginnings, 1947 | AC |
ΔvapH° | 9.367 | kcal/mol | C | Osborne and Ginnings, 1947, 2 | ALS |
Enthalpy of vaporization
ΔvapH (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
ΔfusH (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
ΔfusS (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
12.88 | 183.06 | Huffman, Todd, et al., 1949 | DH |
Gas phase ion energetics data
Go To: Top, 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 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 |
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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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 | NIST Mass Spectrometry Data Center, 1990. |
NIST MS number | 118759 |
References
Go To: Top, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, 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.
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]
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
Go To: Top, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, Mass spectrum (electron ionization), References
- Symbols used in this document:
AE Appearance energy Cp,liquid Constant pressure heat capacity of liquid IE (evaluated) Recommended ionization energy S°liquid Entropy of liquid at standard conditions Tboil Boiling point Tfus Fusion (melting) point Ttriple Triple point temperature ΔcH°liquid Enthalpy of combustion 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
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