Cycloheptane
- Formula: C7H14
- Molecular weight: 98.1861
- IUPAC Standard InChIKey: DMEGYFMYUHOHGS-UHFFFAOYSA-N
- CAS Registry Number: 291-64-5
- Chemical structure:
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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 |
---|---|---|---|---|---|
ΔfH°liquid | -37.39 ± 0.41 | kcal/mol | Ccb | Spitzer and Huffman, 1947 | Reanalyzed by Cox and Pilcher, 1970, Original value = -37.73 ± 0.56 kcal/mol; ALS |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°liquid | -1098.7 ± 0.2 | kcal/mol | Ccb | Kozina, Skuratov, et al., 1961 | Corresponding ΔfHºliquid = -37.9 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS |
ΔcH°liquid | -1098.9 ± 0.1 | kcal/mol | Ccb | Kaarsemaker and Coops, 1952 | Corresponding ΔfHºliquid = -37.72 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS |
ΔcH°liquid | -1099.17 ± 0.40 | kcal/mol | Ccb | Spitzer and Huffman, 1947 | Reanalyzed by Cox and Pilcher, 1970, Original value = -1099.09 ± 0.40 kcal/mol; Corresponding ΔfHºliquid = -37.39 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS |
ΔcH°liquid | -1096.2 | kcal/mol | Ccb | Zubova, 1901 | Corresponding ΔfHºliquid = -40.4 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS |
Quantity | Value | Units | Method | Reference | Comment |
S°liquid | 57.971 | cal/mol*K | N/A | Finke, Scott, et al., 1956 | DH |
Constant pressure heat capacity of liquid
Cp,liquid (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
43.1678 | 298.15 | Fortier, D'Arcy, et al., 1979 | DH |
43.133 | 298.15 | Jolicoeur, Boileau, et al., 1975 | DH |
43.200 | 298.15 | Finke, Scott, et al., 1956 | T = 12 to 300 K.; DH |
Phase change data
Go To: Top, Condensed phase thermochemistry 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:
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
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 | 392.0 ± 0.9 | K | AVG | N/A | Average of 8 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 264. ± 3. | K | AVG | N/A | Average of 6 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
Ttriple | 265. | K | N/A | Finke, Scott, et al., 1956, 2 | Crystal phase 1 phase; Uncertainty assigned by TRC = 0.07 K; TRC |
Ttriple | 265.12 | K | N/A | Finke, Scott, et al., 1956, 2 | Crystal phase 1 phase; Uncertainty assigned by TRC = 0.05 K; TRC |
Ttriple | 265.1 | K | N/A | Kaarsemaker, 1951 | Uncertainty assigned by TRC = 3. K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Tc | 604.2 ± 0.5 | K | N/A | Daubert, 1996 | |
Tc | 604.2 | K | N/A | Hicks and Young, 1971 | Uncertainty assigned by TRC = 0.5 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Pc | 37.7 ± 0.4 | atm | N/A | Daubert, 1996 | |
Pc | 37.63 | atm | N/A | Young, 1972 | Uncertainty assigned by TRC = 0.49 atm; TRC |
Pc | 37.76 | atm | N/A | Hicks and Young, 1971 | Uncertainty assigned by TRC = 0.4000 atm; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Vc | 0.353 | l/mol | N/A | Daubert, 1996 | |
Vc | 0.354 | l/mol | N/A | Young, 1972 | Uncertainty assigned by TRC = 0.007 l/mol; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ρc | 2.83 ± 0.04 | mol/l | N/A | Daubert, 1996 | |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 9.20 | kcal/mol | N/A | Anand, Grolier, et al., 1975 | Based on data from 283. to 323. K.; AC |
ΔvapH° | 9.21 ± 0.50 | kcal/mol | V | Finke, Scott, et al., 1956, 3 | ALS |
ΔvapH° | 9.20 ± 0.05 | kcal/mol | N/A | Finke, Scott, et al., 1956 | AC |
ΔvapH° | 9.42 | kcal/mol | V | Kaarsemaker and Coops, 1952 | ALS |
ΔvapH° | 8.9 | kcal/mol | E | Spitzer and Huffman, 1947 | ALS |
Enthalpy of vaporization
ΔvapH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
9.23 | 297. | A | Stephenson and Malanowski, 1987 | Based on data from 282. to 333. K.; AC |
7.58 | 491. | A | Stephenson and Malanowski, 1987 | Based on data from 476. to 604. K.; AC |
8.70 | 348. | A,EB | Stephenson and Malanowski, 1987 | Based on data from 333. to 398. K. See also Meyer and Hotz, 1976.; AC |
8.63 | 356. | A,EB | Stephenson and Malanowski, 1987 | Based on data from 341. to 433. K. See also Finke, Scott, et al., 1956.; AC |
Antoine Equation Parameters
log10(P) = A − (B / (T + C))
P = vapor pressure (atm)
T = temperature (K)
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Temperature (K) | A | B | C | Reference | Comment |
---|---|---|---|---|---|
341.3 to 432.17 | 3.9714 | 1330.402 | -56.946 | Finke, Scott, et al., 1956 | Coefficents calculated by NIST from author's data. |
Enthalpy of sublimation
ΔsubH (kcal/mol) | Temperature (K) | Reference | Comment |
---|---|---|---|
12.8 | 134. | Bondi, 1963 | AC |
Enthalpy of fusion
ΔfusH (kcal/mol) | Temperature (K) | Reference | Comment |
---|---|---|---|
0.449 | 265.1 | Domalski and Hearing, 1996 | AC |
Entropy of fusion
ΔfusS (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
8.829 | 134.8 | Domalski and Hearing, 1996 | CAL |
0.349 | 198.2 | ||
0.504 | 212.4 | ||
1.7 | 265.1 |
Temperature of phase transition
Ttrs (K) | Initial Phase | Final Phase | Reference | Comment |
---|---|---|---|---|
135.7 | crystaline, IV | crystaline, III | Haines and Gilson, 1990 | DH |
206.3 | crystaline, III | crystaline, I | Haines and Gilson, 1990 | Overlap of the III to II and the II to I transitions.; DH |
Enthalpy of phase transition
ΔHtrs (kcal/mol) | Temperature (K) | Initial Phase | Final Phase | Reference | Comment |
---|---|---|---|---|---|
1.1870 | 134.8 | crystaline, IV | crystaline, III | Finke, Scott, et al., 1956 | DH |
0.06919 | 198.2 | crystaline, III | crystaline, II | Finke, Scott, et al., 1956 | DH |
0.1075 | 212.4 | crystaline, II | crystaline, I | Finke, Scott, et al., 1956 | DH |
0.44981 | 265.12 | crystaline, I | liquid | Finke, Scott, et al., 1956 | DH |
Entropy of phase transition
ΔStrs (cal/mol*K) | Temperature (K) | Initial Phase | Final Phase | Reference | Comment |
---|---|---|---|---|---|
8.805 | 134.8 | crystaline, IV | crystaline, III | Finke, Scott, et al., 1956 | DH |
0.349 | 198.2 | crystaline, III | crystaline, II | Finke, Scott, et al., 1956 | DH |
0.507 | 212.4 | crystaline, II | crystaline, I | Finke, Scott, et al., 1956 | DH |
1.70 | 265.12 | crystaline, I | liquid | Finke, Scott, et al., 1956 | 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:
B - John E. Bartmess
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) | 9.9 ± 0.1 | eV | N/A | N/A | L |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
9.82 ± 0.05 | EI | Holmes and Lossing, 1991 | LL |
9.96 | EQ | Sieck and Mautner(Meot-Ner), 1982 | LBLHLM |
9.97 | PE | Puttemans, 1974 | LLK |
9.88 ± 0.05 | EI | Puttemans, 1974 | LLK |
De-protonation reactions
C7H13- + =
By formula: C7H13- + H+ = C7H14
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 415.6 ± 4.8 | kcal/mol | Bran | Peerboom, Rademaker, et al., 1992 | gas phase; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 406.7 ± 4.9 | kcal/mol | H-TS | Peerboom, Rademaker, et al., 1992 | gas phase; B |
Mass spectrum (electron ionization)
Go To: Top, Condensed phase thermochemistry data, Phase change data, 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 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 | Japan AIST/NIMC Database- Spectrum MS-NW-3926 |
NIST MS number | 231525 |
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.
Spitzer and Huffman, 1947
Spitzer, R.; Huffman, H.M.,
The heats of combustion of cyclopentane, cyclohexane, cycloheptane and cyclooctane,
J. Am. Chem. Soc., 1947, 69, 211-213. [all data]
Cox and Pilcher, 1970
Cox, J.D.; Pilcher, G.,
Thermochemistry of Organic and Organometallic Compounds, Academic Press, New York, 1970, 1-636. [all data]
Kozina, Skuratov, et al., 1961
Kozina, M.P.; Skuratov, S.M.; Shtekher, S.M.; Sosnina, I.E.; Turova-Polyak, M.B.,
Heats of combustion of some bicyclanes,
Russ. J. Phys. Chem. (Engl. Transl.), 1961, 35, 1144-1146. [all data]
Kaarsemaker and Coops, 1952
Kaarsemaker, S.; Coops, J.,
Thermal quantities of some cycloparaffins. Part III. Results of measurements,
Rec. Trav. Chim. Pays/Bas, 1952, 71, 261. [all data]
Zubova, 1901
Zubova, P.,
Data about heat of combustion of compound cycle structure,
Zh. Fiz. Khim., 1901, 33, 708-722. [all data]
Finke, Scott, et al., 1956
Finke, H.L.; Scott, D.W.; Gross, M.E.; Messerly, J.F.; Waddington, G.,
Cycloheptane, cyclooctane and 1,3,5-cycloheptatriene. Low temperature thermal properties, vapor pressure and derived chemical thermodynamic properties,
J. Am. Chem. Soc., 1956, 78, 5469-5476. [all data]
Fortier, D'Arcy, et al., 1979
Fortier, J.-L.; D'Arcy, P.J.; Benson, G.C.,
Heat capacities of binary cycloalkane mixtures at 298.15 K,
Thermochim. Acta, 1979, 28, 37-43. [all data]
Jolicoeur, Boileau, et al., 1975
Jolicoeur, C.; Boileau, J.; Bazinet, S.; Picker, P.,
Thermodynamic properties of aqueous organic solutes in relation to their structure. Part II. Apparent molal volumes and heat capacities of c-alkylamine hydrobromides in water,
Can. J. Chem., 1975, 53, 716-722. [all data]
Finke, Scott, et al., 1956, 2
Finke, H.L.; Scott, D.W.; Gross, M.E.; Messerly, J.F.; Waddington, G.,
Cycloheptane, Cyclooctane and 1,3,5-Cycloheptatriene. Low Temperature Thermal Properties, Vapor Pressure and Derived Chemical Thermodynamic Prop.,
J. Am. Chem. Soc., 1956, 78, 5469. [all data]
Kaarsemaker, 1951
Kaarsemaker, S.,
, Thesis, 1951. [all data]
Daubert, 1996
Daubert, T.E.,
Vapor-Liquid Critical Properties of Elements and Compounds. 5. Branched Alkanes and Cycloalkanes,
J. Chem. Eng. Data, 1996, 41, 365-372. [all data]
Hicks and Young, 1971
Hicks, C.P.; Young, C.L.,
Critical Temperatures of Mixtures of Quasi-spherical Molecules. Alicyclic Hydrocarbons + Benzene, + Hexafluorobenzene and + Perfluorocyclohexane,
Trans. Faraday Soc., 1971, 67, 1605-11. [all data]
Young, 1972
Young, C.L.,
Gas-liquid critical properties of the cycloalkanes and their mixtures,
Aust. J. Chem., 1972, 25, 1625-30. [all data]
Anand, Grolier, et al., 1975
Anand, Subhash C.; Grolier, Jean P.E.; Kiyohara, Osamu; Halpin, Carl J.; Benson, George C.,
Thermodynamic properties of some cycloalkane-cycloalkanol systems at 298. 15K. III,
J. Chem. Eng. Data, 1975, 20, 2, 184-189, https://doi.org/10.1021/je60065a020
. [all data]
Finke, Scott, et al., 1956, 3
Finke, H.L.; Scott, D.W.; Gross, M.E.; Messerly, J.F.; Waddington, G.,
Cycloheptane, cyclooctane and 1,3,5-cycloheptatriene. Low temperature thermal properties, vapor pressure and derived chemical thermodynamic properties,
J. Am. Chem. Soc., 1956, 78, 5469-54. [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]
Meyer and Hotz, 1976
Meyer, Edwin F.; Hotz, Carol A.,
Cohesive energies in polar organic liquids. 3. Cyclic ketones,
J. Chem. Eng. Data, 1976, 21, 3, 274-279, https://doi.org/10.1021/je60070a035
. [all data]
Bondi, 1963
Bondi, A.,
Heat of Siblimation of Molecular Crystals: A Catalog of Molecular Structure Increments.,
J. Chem. Eng. Data, 1963, 8, 3, 371-381, https://doi.org/10.1021/je60018a027
. [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]
Haines and Gilson, 1990
Haines, J.; Gilson, D.F.R.,
Investigation of the phase transition behavior in solid cycloheptane,
J. Phys. Chem., 1990, 94, 3156-3160. [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]
Puttemans, 1974
Puttemans, J.P.,
Ionisation de cycloalcanes (C5 a C12) en spectroscopie photoelectronique et par impact electronique,
Ing. Chim. (Brussels), 1974, 56, 64. [all data]
Peerboom, Rademaker, et al., 1992
Peerboom, R.A.L.; Rademaker, G.J.; Dekoning, L.J.; Nibbering, N.M.M.,
Stabilization of Cycloalkyl Carbanions in the Gas Phase,
Rapid Commun. Mass Spectrom., 1992, 6, 6, 394, https://doi.org/10.1002/rcm.1290060608
. [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:
Cp,liquid Constant pressure heat capacity of liquid IE (evaluated) Recommended ionization energy Pc Critical pressure S°liquid Entropy of liquid at standard conditions Tboil Boiling point Tc Critical temperature Tfus Fusion (melting) point Ttriple Triple point temperature Ttrs Temperature of phase transition Vc Critical volume ΔHtrs Enthalpy of phase transition ΔStrs Entropy of phase transition ΔcH°liquid Enthalpy of combustion of liquid at standard conditions ΔfH°liquid Enthalpy of formation of liquid at standard conditions ΔfusH Enthalpy of fusion ΔfusS Entropy of fusion ΔrG° Free energy of reaction at standard conditions ΔrH° Enthalpy of reaction at standard conditions ΔsubH Enthalpy of sublimation ΔvapH Enthalpy of vaporization ΔvapH° Enthalpy of vaporization at standard conditions ρc Critical density - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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