Cyclopentane, 1,2-dimethyl-, cis-
- Formula: C7H14
- Molecular weight: 98.1861
- IUPAC Standard InChIKey: RIRARCHMRDHZAR-KNVOCYPGSA-N
- CAS Registry Number: 1192-18-3
- 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-1,2-Dimethylcyclopentane; 1,cis-2-Dimethylcyclopentane; 1,2-Dimethyl- cis-cyclopentane; 1,2-Dimethylcyclopentane, cis; 1-c-2-Dimethylcyclopentane; c-1,2-Dimethylcyclopentane
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Gas phase thermochemistry data
Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, 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
GT - Glushko Thermocenter, Russian Academy of Sciences, Moscow
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°gas | -30.96 ± 0.32 | kcal/mol | Cm | Johnson, Prosen, et al., 1949 | ALS |
Quantity | Value | Units | Method | Reference | Comment |
S°gas | 87.510 | cal/mol*K | N/A | Stull D.R., 1969 | This value was obtained using low temperature data of [ Gross M.E., 1953].; GT |
Constant pressure heat capacity of gas
Cp,gas (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
10.69 | 50. | Thermodynamics Research Center, 1997 | p=1 bar. Recommended values are in close agreement with those calculated by a method of increments [ Epstein M.B., 1949] at low temperatures. Discrepancies increase up to 2-4 J/mol*K at T=1500 K.; GT |
14.74 | 100. | ||
18.33 | 150. | ||
22.15 | 200. | ||
29.28 | 273.15 | ||
32.05 | 298.15 | ||
32.27 | 300. | ||
43.59 | 400. | ||
53.82 | 500. | ||
62.38 | 600. | ||
69.50 | 700. | ||
75.50 | 800. | ||
80.62 | 900. | ||
84.99 | 1000. | ||
88.74 | 1100. | ||
91.97 | 1200. | ||
94.74 | 1300. | ||
97.16 | 1400. | ||
99.24 | 1500. | ||
103.4 | 1750. | ||
106.4 | 2000. | ||
108.6 | 2250. | ||
110.2 | 2500. | ||
111.5 | 2750. | ||
112.5 | 3000. |
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 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 | -39.52 ± 0.31 | kcal/mol | Cm | Johnson, Prosen, et al., 1949 | ALS |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°liquid | -1097.06 ± 0.30 | kcal/mol | Cm | Johnson, Prosen, et al., 1949 | Corresponding ΔfHºliquid = -39.50 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS |
Quantity | Value | Units | Method | Reference | Comment |
S°liquid | 64.331 | cal/mol*K | N/A | Gross, Oliver, et al., 1953 | DH |
Constant pressure heat capacity of liquid
Cp,liquid (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
45.569 | 302.84 | Gross, Oliver, et al., 1953 | T = 13 to 300 K. Unsmoothed experimental datum.; 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:
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
DRB - Donald R. Burgess, Jr.
CAL - James S. Chickos, William E. Acree, Jr., Joel F. Liebman, Students of Chem 202 (Introduction to the Literature of Chemistry), University of Missouri -- St. Louis
DH - Eugene S. Domalski and Elizabeth D. Hearing
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tboil | 372.5 ± 0.3 | K | AVG | N/A | Average of 13 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 230. ± 70. | K | AVG | N/A | Average of 9 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
Ttriple | 219.45 | K | N/A | Gross, Oliver, et al., 1953, 2 | Crystal phase 1 phase; Uncertainty assigned by TRC = 0.05 K; TRC |
Ttriple | 219.430 | K | N/A | Huffman, 1948 | Crystal phase 1 phase; Uncertainty assigned by TRC = 0.06 K; TRC |
Ttriple | 219.430 | K | N/A | Huffman, 1948 | Crystal phase 1 phase; Uncertainty assigned by TRC = 0.04 K; TRC |
Ttriple | 219.430 | K | N/A | Huffman, 1947 | Crystal phase 1 phase; Uncertainty assigned by TRC = 0.04 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 8.56 | kcal/mol | N/A | Reid, 1972 | AC |
ΔvapH° | 8.58 | kcal/mol | N/A | Johnson, Prosen, et al., 1949 | DRB |
Enthalpy of vaporization
ΔvapH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
8.48 | 308. | A | Stephenson and Malanowski, 1987 | Based on data from 293. to 375. K.; AC |
8.41 | 313. | N/A | Forziati, Norris, et al., 1949 | Based on data from 298. to 373. K.; AC |
Enthalpy of fusion
ΔfusH (kcal/mol) | Temperature (K) | Reference | Comment |
---|---|---|---|
0.397 | 219.4 | Domalski and Hearing, 1996 | AC |
Entropy of fusion
ΔfusS (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
11.24 | 141.5 | Domalski and Hearing, 1996 | CAL |
1.80 | 219.4 |
Enthalpy of phase transition
ΔHtrs (kcal/mol) | Temperature (K) | Initial Phase | Final Phase | Reference | Comment |
---|---|---|---|---|---|
1.5939 | 141.50 | crystaline, II | crystaline, I | Gross, Oliver, et al., 1953 | DH |
0.39610 | 219.45 | crystaline, I | liquid | Gross, Oliver, et al., 1953 | DH |
Entropy of phase transition
ΔStrs (cal/mol*K) | Temperature (K) | Initial Phase | Final Phase | Reference | Comment |
---|---|---|---|---|---|
11.26 | 141.50 | crystaline, II | crystaline, I | Gross, Oliver, et al., 1953 | DH |
1.80 | 219.45 | crystaline, I | liquid | Gross, Oliver, et al., 1953 | DH |
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 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
By formula: 2H2 + 2C7H12 = C7H14 + C7H14
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -22.55 ± 0.18 | kcal/mol | Chyd | Allinger, Dodziuk, et al., 1982 | liquid phase; solvent: Hexane |
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: Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
Ionization energy determinations
IE (eV) | Method | Reference |
---|---|---|
9.92 ± 0.05 | EI | Herzschuh and Sicker, 1981 |
Appearance energy determinations
Ion | AE (eV) | Other Products | Method | Reference | Comment |
---|---|---|---|---|---|
C5H11+ | 10.47 ± 0.05 | C2H5 | EI | Herzschuh and Sicker, 1981 | |
C6H11+ | 10.57 ± 0.05 | CH3 | EI | Herzschuh and Sicker, 1981 |
IR Spectrum
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Data compiled by: Coblentz Society, Inc.
- GAS (30 mmHg, N2 ADDED, TOTAL PRESSURE 600 mmHg); DOW KBr FOREPRISM-GRATING; DIGITIZED BY COBLENTZ SOCIETY (BATCH II) FROM HARD COPY; 2 cm-1 resolution
- SOLUTION (10% IN CCl4 FOR 3800-1330, 10% IN CS2 FOR 1330-400 CM-1); BECKMAN IR-9 (GRATING); DIGITIZED BY NIST FROM HARD COPY (FROM TWO SEGMENTS); 4 cm-1 resolution
Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director
Mass spectrum (electron ionization)
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, 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
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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. |
---|---|
Origin | NIST Mass Spectrometry Data Center, 1990. |
NIST MS number | 114027 |
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), 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., 1949
Johnson, W.H.; Prosen, E.J.; Rossini, F.D.,
Heats of combustion and isomerization of the six C7H14 alkylcyclopentanes,
J. Res. NBS, 1949, 42, 251-255. [all data]
Stull D.R., 1969
Stull D.R., Jr.,
The Chemical Thermodynamics of Organic Compounds. Wiley, New York, 1969. [all data]
Gross M.E., 1953
Gross M.E.,
Low-temperature thermal data for some C7H14 alkylcyclopentanes,
J. Am. Chem. Soc., 1953, 75, 2801-2804. [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]
Epstein M.B., 1949
Epstein M.B.,
Heats, equilibrium constants, and free energies of formation of the dimethylcyclopentanes,
J. Res. Nat. Bur. Stand., 1949, 43, 245-250. [all data]
Gross, Oliver, et al., 1953
Gross, M.E.; Oliver, G.D.; Huffman, H.M.,
Low-temperature thermal data for some C7H14 alkylcyclopentanes,
J. Am. Chem. Soc., 1953, 75, 2801-2804. [all data]
Gross, Oliver, et al., 1953, 2
Gross, M.E.; Oliver, G.D.; Huffman, H.M.,
Low temperature thermal data for some C7H14 alkylcyclopentanes,
J. Am. Chem. Soc., 1953, 75, 2801. [all data]
Huffman, 1948
Huffman, H.M.,
Personal Commun., U. S. Bur. Mines, Bartlesville, OK, 1948. [all data]
Huffman, 1947
Huffman, H.M.,
Personal Communication, U. S. Bur. Mines, Bartlesville, OK, 1947. [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]
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]
Forziati, Norris, et al., 1949
Forziati, Alphonse F.; Norris, William R.; Rossini, Frederick D.,
Vapor pressures and boiling points of sixty API-NBS hydrocarbons,
J. RES. NATL. BUR. STAN., 1949, 43, 6, 555-17, https://doi.org/10.6028/jres.043.050
. [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]
Allinger, Dodziuk, et al., 1982
Allinger, N.L.; Dodziuk, H.; Rogers, D.W.; Naik, S.N.,
Heats of hydrogenation and formation of some 5-membered ring compounds by molecular mechanics calculations and direct measurements,
Tetrahedron, 1982, 38, 1593-1597. [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, 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), References
- Symbols used in this document:
AE Appearance energy Cp,gas Constant pressure heat capacity of gas Cp,liquid Constant pressure heat capacity of liquid S°gas Entropy of gas at standard conditions S°liquid Entropy of liquid at standard conditions Tboil Boiling point Tfus Fusion (melting) point Ttriple Triple point temperature ΔHtrs Enthalpy of phase transition ΔStrs Entropy of phase transition 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 ΔrH° Enthalpy of reaction at standard conditions 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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