Cyclohexane
- Formula: C6H12
- Molecular weight: 84.1595
- IUPAC Standard InChIKey: XDTMQSROBMDMFD-UHFFFAOYSA-N
- CAS Registry Number: 110-82-7
- 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. - Isotopologues:
- Other names: Benzene, hexahydro-; Hexahydrobenzene; Hexamethylene; Hexanaphthene; Cicloesano; Cykloheksan; Rcra waste number U056; UN 1145; NSC 406835
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Gas phase thermochemistry data
Go To: Top, Reaction thermochemistry 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 as indicated in comments:
DRB - Donald R. Burgess, Jr.
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 | -29.78 | kcal/mol | N/A | Spitzer and Huffman, 1947 | Value computed using ΔfHliquid° value of -157.7±1.8 kj/mol from Spitzer and Huffman, 1947 and ΔvapH° value of 33.1 kj/mol from Prosen, Johnson, et al., 1946.; DRB |
ΔfH°gas | -29.43 ± 0.19 | kcal/mol | Ccb | Prosen, Johnson, et al., 1946 | ALS |
ΔfH°gas | -29.47 | kcal/mol | N/A | Moore, Renquist, et al., 1940 | Value computed using ΔfHliquid° value of -156.4±1.3 kj/mol from Moore, Renquist, et al., 1940 and ΔvapH° value of 33.1 kj/mol from Prosen, Johnson, et al., 1946.; DRB |
Quantity | Value | Units | Method | Reference | Comment |
S°gas | 71.269 | cal/mol*K | N/A | Beckett C.W., 1947 | Close value of S(298.15 K)=298.78(0.75) J/mol*K was obtained by [43ASTSZA] from calorimetric data.; GT |
Constant pressure heat capacity of gas
Cp,gas (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
8.143 | 50. | Dorofeeva O.V., 1986 | There is an appreciable difference (up to 3.0-4.5 J/mol*K) between selected values of S(T) and Cp(T) and earlier statistically calculated values [ Brickwedde F.G., 1946, Beckett C.W., 1947, Kilpatrick J.E., 1947, Lippincott E.R., 1966] at high temperatures. It is due to using the most reliable molecular constants in [ Dorofeeva O.V., 1986].; GT |
10.18 | 100. | ||
13.10 | 150. | ||
16.50 | 200. | ||
22.75 | 273.15 | ||
25.18 ± 0.48 | 298.15 | ||
25.361 | 300. | ||
35.526 | 400. | ||
45.096 | 500. | ||
53.389 | 600. | ||
60.378 | 700. | ||
66.217 | 800. | ||
71.085 | 900. | ||
75.148 | 1000. | ||
78.552 | 1100. | ||
81.417 | 1200. | ||
83.841 | 1300. | ||
85.908 | 1400. | ||
87.679 | 1500. |
Constant pressure heat capacity of gas
Cp,gas (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
33.000 | 370. | Spitzer R., 1946 | Please also see Montgomery J.B., 1942.; GT |
34.21 ± 0.30 | 384. | ||
35.000 | 390. | ||
36.800 | 410. | ||
38.67 ± 0.40 | 428. | ||
41.70 ± 0.40 | 460. | ||
45.30 ± 0.50 | 495. | ||
47.00 ± 0.50 | 521. | ||
49.30 ± 0.50 | 544. |
Reaction thermochemistry data
Go To: Top, Gas phase thermochemistry 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 as indicated in comments:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
M - Michael M. Meot-Ner (Mautner) and Sharon G. Lias
B - John E. Bartmess
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: C6H10 + H2 = C6H12
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -28. ± 1. | kcal/mol | AVG | N/A | Average of 8 values; Individual data points |
By formula: H4N+ + C6H12 = (H4N+ • C6H12)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 9. | kcal/mol | PHPMS | Deakyne and Meot-Ner (Mautner), 1985 | gas phase; Entropy change calculated or estimated, DG<, ΔrH<; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 20. | cal/mol*K | N/A | Deakyne and Meot-Ner (Mautner), 1985 | gas phase; Entropy change calculated or estimated, DG<, ΔrH<; M |
Free energy of reaction
ΔrG° (kcal/mol) | T (K) | Method | Reference | Comment |
---|---|---|---|---|
2.8 | 317. | PHPMS | Deakyne and Meot-Ner (Mautner), 1985 | gas phase; Entropy change calculated or estimated, DG<, ΔrH<; M |
By formula: C6H6+ + C6H12 = (C6H6+ • C6H12)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 11.2 | kcal/mol | PHPMS | Meot-Ner (Mautner), Hamlet, et al., 1978 | gas phase; Entropy change calculated or estimated; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 27. | cal/mol*K | N/A | Meot-Ner (Mautner), Hamlet, et al., 1978 | gas phase; Entropy change calculated or estimated; M |
Free energy of reaction
ΔrG° (kcal/mol) | T (K) | Method | Reference | Comment |
---|---|---|---|---|
3.2 | 295. | PHPMS | Meot-Ner (Mautner), Hamlet, et al., 1978 | gas phase; Entropy change calculated or estimated; M |
C6H11- + =
By formula: C6H11- + H+ = C6H12
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 418.3 ± 2.0 | kcal/mol | Bran | Peerboom, Rademaker, et al., 1992 | gas phase; B |
ΔrH° | 406.82 ± 0.90 | kcal/mol | G+TS | Bohme, Lee-Ruff, et al., 1972 | gas phase; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 409.5 ± 2.2 | kcal/mol | H-TS | Peerboom, Rademaker, et al., 1992 | gas phase; B |
ΔrG° | >398.00 | kcal/mol | IMRB | Bohme, Lee-Ruff, et al., 1972 | gas phase; B |
By formula: 2H2 + C6H8 = C6H12
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -53.64 ± 0.29 | kcal/mol | Chyd | Turner, Mallon, et al., 1973 | liquid phase; solvent: Glacial acetic acid; ALS |
ΔrH° | -54.88 ± 0.10 | kcal/mol | Chyd | Kistiakowsky, Ruhoff, et al., 1936 | gas phase; Reanalyzed by Cox and Pilcher, 1970, Original value = -55.4 ± 0.1 kcal/mol; At 355 °K; ALS |
By formula: 2H2 + C6H8 = C6H12
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -55.6 | kcal/mol | Chyd | Roth, Adamczak, et al., 1991 | liquid phase; ALS |
ΔrH° | -53.90 ± 0.33 | kcal/mol | Chyd | Turner, Mallon, et al., 1973 | liquid phase; solvent: Glacial acetic acid; ALS |
By formula: C3H9Si+ + C6H12 = (C3H9Si+ • C6H12)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 37.9 | kcal/mol | PHPMS | Li and Stone, 1989 | gas phase; condensation; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 48.1 | cal/mol*K | PHPMS | Li and Stone, 1989 | gas phase; condensation; M |
By formula: 3H2 + C6H6 = C6H12
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -49.06 ± 0.15 | kcal/mol | Chyd | Kistiakowsky, Ruhoff, et al., 1936 | gas phase; Reanalyzed by Cox and Pilcher, 1970, Original value = -49.80 ± 0.15 kcal/mol; At 355 °K; ALS |
By formula: HI + C6H11I = C6H12 + I2
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -7.8 ± 2.0 | kcal/mol | Cm | Brennan and Ubbelohde, 1956 | gas phase; Reanalyzed by Cox and Pilcher, 1970, Original value = -6.8 ± 1.0 kcal/mol; ALS |
By formula: Li+ + C6H12 = (Li+ • C6H12)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 24. | kcal/mol | ICR | Staley and Beauchamp, 1975 | gas phase; switching reaction(Li+)H2O, from graph; Dzidic and Kebarle, 1970 extrapolated; M |
By formula: C6H12 = C6H12
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -3.510 | kcal/mol | Eqk | Glasebrook and Lovell, 1939 | liquid phase; Heat of isomerization; ALS |
By formula: 2H2 + C6H8 = C6H12
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -102.0 ± 1.9 | kcal/mol | Chyd | Roth, Adamczak, et al., 1991 | liquid phase; ALS |
By formula: C6H12O = C6H12 + H2
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 15.2 ± 0.55 | kcal/mol | Eqk | Fedoseenko, Yursha, et al., 1983 | gas phase; At 502 K; ALS |
By formula: C6H11Cl + HCl = C6H12 + Cl2
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -34.20 | kcal/mol | Cm | Kirkbride, 1956 | liquid phase; ALS |
By formula: C6H12 = C6H12
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 4.32 ± 0.28 | kcal/mol | Eqk | Kabo and Andreevskii, 1973 | liquid phase; ALS |
Gas phase ion energetics data
Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry data, 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:
HL - Edward P. Hunter and Sharon G. Lias
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
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron
View reactions leading to C6H12+ (ion structure unspecified)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
IE (evaluated) | 9.88 ± 0.03 | eV | N/A | N/A | L |
Quantity | Value | Units | Method | Reference | Comment |
Proton affinity (review) | 164.2 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
Quantity | Value | Units | Method | Reference | Comment |
Gas basicity | 159.4 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
9.80 ± 0.05 | EI | Holmes and Lossing, 1991 | LL |
10.0 ± 0.03 | EI | Arimura and Yoshikawa, 1984 | LBLHLM |
9.82 | EQ | Sieck and Mautner(Meot-Ner), 1982 | LBLHLM |
9.88 ± 0.10 | EQ | Lias, 1982 | LBLHLM |
9.88 | PE | Kovac and Klasinc, 1978 | LLK |
9.88 ± 0.02 | PE | Bieri, Burger, et al., 1977 | LLK |
9.88 | EI | Lossing and Traeger, 1975 | LLK |
9.89 ± 0.01 | PE | Rang, Paldoia, et al., 1974 | LLK |
9.83 ± 0.05 | EI | Puttemans, 1974 | LLK |
9.84 | PE | Puttemans, 1974 | LLK |
9.88 ± 0.01 | PI | Sergeev, Akopyan, et al., 1973 | LLK |
9.87 | PE | Ikuta, Yoshihara, et al., 1973 | LLK |
9.88 ± 0.01 | S | Raymonda, 1972 | LLK |
9.89 | PE | Demeo and Yencha, 1970 | RDSH |
9.81 | PE | Dewar and Worley, 1969 | RDSH |
9.79 | PE | Al-Joboury and Turner, 1964 | RDSH |
9.88 ± 0.02 | PI | Watanabe, 1957 | RDSH |
11.0 ± 0.2 | EI | Hustrulid, Kusch, et al., 1938 | RDSH |
10.32 | PE | Kimura, Katsumata, et al., 1981 | Vertical value; LLK |
10.3 ± 0.1 | PE | Bieri, Burger, et al., 1977 | Vertical value; LLK |
10.3 | PE | Bruckmann and Klessinger, 1973 | Vertical value; LLK |
Appearance energy determinations
Ion | AE (eV) | Other Products | Method | Reference | Comment |
---|---|---|---|---|---|
C3H5+ | 13.20 ± 0.08 | C3H7 | EI | Rabbih, Selim, et al., 1981 | LLK |
C3H6+ | 12.00 ± 0.07 | C3H6 | EI | Rabbih, Selim, et al., 1981 | LLK |
C3H6+ | 11.23 ± 0.04 | C3H6 | PI | Sergeev, Akopyan, et al., 1973 | LLK |
C3H7+ | 13.50 ± 0.08 | C3H5 | EI | Rabbih, Selim, et al., 1981 | LLK |
C3H7+ | 11.49 ± 0.03 | C3H5 | PI | Sergeev, Akopyan, et al., 1973 | LLK |
C4H7+ | 11.21 ± 0.04 | C2H5 | PI | Sergeev, Akopyan, et al., 1973 | LLK |
C4H8+ | 11.15 ± 0.03 | C2H4 | EI | Rabbih, Selim, et al., 1981 | LLK |
C4H8+ | 11.45 | C2H4 | EI | Puttemans, 1974 | LLK |
C4H8+ | 11.08 ± 0.01 | C2H4 | PI | Sergeev, Akopyan, et al., 1973 | LLK |
C5H9+ | 9.88 | CH3 | EI | Lossing and Traeger, 1975, 2 | LLK |
C5H9+ | ≤11.06 | CH3 | EI | Lossing and Traeger, 1975 | LLK |
C5H9+ | 11.15 | CH3 | EI | Puttemans, 1974 | LLK |
C5H9+ | 11.07 ± 0.04 | CH3 | PI | Sergeev, Akopyan, et al., 1973 | LLK |
C6H11+ | 11.32 ± 0.05 | H | PI | Sergeev, Akopyan, et al., 1973 | LLK |
C6H11+ | 11.66 | H | EI | Pottie, Harrison, et al., 1961 | RDSH |
De-protonation reactions
C6H11- + =
By formula: C6H11- + H+ = C6H12
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 418.3 ± 2.0 | kcal/mol | Bran | Peerboom, Rademaker, et al., 1992 | gas phase; B |
ΔrH° | 406.82 ± 0.90 | kcal/mol | G+TS | Bohme, Lee-Ruff, et al., 1972 | gas phase; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 409.5 ± 2.2 | kcal/mol | H-TS | Peerboom, Rademaker, et al., 1992 | gas phase; B |
ΔrG° | >398.00 | kcal/mol | IMRB | Bohme, Lee-Ruff, et al., 1972 | gas phase; B |
References
Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry 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.
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]
Prosen, Johnson, et al., 1946
Prosen, E.J.; Johnson, W.H.; Rossini, F.D.,
Heats of formation and combustion of the normal alkylcyclopentanes and cyclohexanes and the increment per CH2 group for several homologous series of hydrocarbons,
J. Res. NBS, 1946, 37, 51-56. [all data]
Moore, Renquist, et al., 1940
Moore, G.E.; Renquist, M.L.; Parks, G.S.,
Thermal data on organic compounds. XX. Modern combustion data for two methylnonanes, methyl ethyl ketone, thiophene and six cycloparaffins,
J. Am. Chem. Soc., 1940, 62, 1505-1507. [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]
Dorofeeva O.V., 1986
Dorofeeva O.V.,
Thermodynamic properties of twenty-one monocyclic hydrocarbons,
J. Phys. Chem. Ref. Data, 1986, 15, 437-464. [all data]
Brickwedde F.G., 1946
Brickwedde F.G.,
Equilibrium constants of some reactions involved in the production of 1,3-butadiene,
J. Res. Nat. Bur. Stand., 1946, 37, 263-279. [all data]
Kilpatrick J.E., 1947
Kilpatrick J.E.,
Heats, equilibrium constants, and free energies of formation of the alkylcyclopentanes and alkylcyclohexanes,
J. Res. Nat. Bur. Stand., 1947, 39, 523-543. [all data]
Lippincott E.R., 1966
Lippincott E.R.,
Enthalpy, free energy, entropy, and heat capacity of cyclohexane and acetaldehyde,
Bull. Soc. Chim. Belges., 1966, 75, 655-667. [all data]
Spitzer R., 1946
Spitzer R.,
The heat capacity of gaseous cyclopentane, cyclohexane and methylcyclohexane,
J. Am. Chem. Soc., 1946, 68, 2537-2538. [all data]
Montgomery J.B., 1942
Montgomery J.B.,
The heat capacity of organic vapors. IV. Benzene, fluorobenzene, toluene, cyclohexane, methylcyclohexane and cyclohexene,
J. Am. Chem. Soc., 1942, 64, 2375-2377. [all data]
Deakyne and Meot-Ner (Mautner), 1985
Deakyne, C.A.; Meot-Ner (Mautner), M.,
Unconventional Ionic Hydrogen Bonds. 2. NH+ pi. Complexes of Onium Ions with Olefins and Benzene Derivatives,
J. Am. Chem. Soc., 1985, 107, 2, 474, https://doi.org/10.1021/ja00288a034
. [all data]
Meot-Ner (Mautner), Hamlet, et al., 1978
Meot-Ner (Mautner), M.; Hamlet, P.; Hunter, E.P.; Field, F.H.,
Bonding Energies in Association Ions of Aromatic Molecules. Correlations with Ionization Energies,
J. Am. Chem. Soc., 1978, 100, 17, 5466, https://doi.org/10.1021/ja00485a034
. [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]
Bohme, Lee-Ruff, et al., 1972
Bohme, D.K.; Lee-Ruff, E.; Young, L.B.,
Acidity order of selected bronsted acids in the gas phase at 300K,
J. Am. Chem. Soc., 1972, 94, 5153. [all data]
Turner, Mallon, et al., 1973
Turner, R.B.; Mallon, B.J.; Tichy, M.; Doering, W.v.E.; Roth, W.R.; Schroder, G.,
Heats of hydrogenation. X. Conjugative interaction in cyclic dienes and trienes,
J. Am. Chem. Soc., 1973, 95, 8605-8610. [all data]
Kistiakowsky, Ruhoff, et al., 1936
Kistiakowsky, G.B.; Ruhoff, J.R.; Smith, H.A.; Vaughan, W.E.,
Heats of organic reactions. IV. Hydrogenation of some dienes and of benzene,
J. Am. Chem. Soc., 1936, 58, 146-153. [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]
Roth, Adamczak, et al., 1991
Roth, W.R.; Adamczak, O.; Breuckmann, R.; Lennartz, H.-W.; Boese, R.,
Die Berechnung von Resonanzenergien; das MM2ERW-Kraftfeld,
Chem. Ber., 1991, 124, 2499-2521. [all data]
Li and Stone, 1989
Li, X.; Stone, J.A.,
Determination of the beta silicon effect from a mass spectrometric study of the association of trimethylsilylium ion with alkenes,
J. Am. Chem. Soc., 1989, 111, 15, 5586, https://doi.org/10.1021/ja00197a013
. [all data]
Brennan and Ubbelohde, 1956
Brennan, D.; Ubbelohde, A.R.,
A thermochemical evaluation of bond strengths in some carbon compounds. Part IV. Bond-strength differences based on the reaction: RI + HI = RH + I2, where R = p-methoxyphenyl and cyclohexyl,
J. Chem. Soc., 1956, 3011-3016. [all data]
Staley and Beauchamp, 1975
Staley, R.H.; Beauchamp, J.L.,
Intrinsic Acid - Base Properties of Molecules. Binding Energies of Li+ to pi - and n - Donor Bases,
J. Am. Chem. Soc., 1975, 97, 20, 5920, https://doi.org/10.1021/ja00853a050
. [all data]
Dzidic and Kebarle, 1970
Dzidic, I.; Kebarle, P.,
Hydration of the Alkali Ions in the Gas Phase. Enthalpies and Entropies of Reactions M+(H2O)n-1 + H2O = M+(H2O)n,
J. Phys. Chem., 1970, 74, 7, 1466, https://doi.org/10.1021/j100702a013
. [all data]
Glasebrook and Lovell, 1939
Glasebrook, A.L.; Lovell, W.G.,
The isomerization of cyclohexane and methylcyclopentane,
J. Am. Chem. Soc., 1939, 61, 1717-1720. [all data]
Fedoseenko, Yursha, et al., 1983
Fedoseenko, V.I.; Yursha, I.A.; Kabo, G.Ya.,
Equilibrium and thermodynamics of cyclohexanol dehydrogenation reactions,
Dokl. Akad. Nauk BSSR, 1983, 27, 926-929. [all data]
Kirkbride, 1956
Kirkbride, F.W.,
The heats of chlorination of some hydrocarbons and their chloro-derivatives,
J. Appl. Chem., 1956, 6, 11-21. [all data]
Kabo and Andreevskii, 1973
Kabo, G.Ya.; Andreevskii, D.N.,
Thermodynamic characteristics of the cyclohexane = methylcyclopentane isomerization,
Zh. Fiz. Khim., 1973, 47, 272-273. [all data]
Hunter and Lias, 1998
Hunter, E.P.; Lias, S.G.,
Evaluated Gas Phase Basicities and Proton Affinities of Molecules: An Update,
J. Phys. Chem. Ref. Data, 1998, 27, 3, 413-656, https://doi.org/10.1063/1.556018
. [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]
Arimura and Yoshikawa, 1984
Arimura, M.; Yoshikawa, Y.,
Ionization efficiency and ionization energy of cyclic compounds by electron impact,
Mass Spectrosc. (Tokyo), 1984, 32, 375. [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]
Lias, 1982
Lias, S.G.,
Thermochemical information from ion-molecule rate constants,
Ion Cyclotron Reson. Spectrom. 1982, 1982, 409. [all data]
Kovac and Klasinc, 1978
Kovac, B.; Klasinc, L.,
Photoelectron spectroscopy of adamantane and some adamantanones,
Croat. Chem. Acta, 1978, 51, 55. [all data]
Bieri, Burger, et al., 1977
Bieri, G.; Burger, F.; Heilbronner, E.; Maier, J.P.,
Valence ionization enrgies of hydrocarbons,
Helv. Chim. Acta, 1977, 60, 2213. [all data]
Lossing and Traeger, 1975
Lossing, F.P.; Traeger, J.C.,
Stabilization in cyclopentadienyl, cyclopentenyl, and cyclopentyl cations,
J. Am. Chem. Soc., 1975, 97, 1579. [all data]
Rang, Paldoia, et al., 1974
Rang, S.; Paldoia, P.; Talvari, A.,
Ionization potentials of unsaturated hydrocarbons. 2. Mono-substituted cyclopentenes and cyclohexenes,
Eesti. NSV Tead. Akad. Toim., 1974, 354. [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]
Sergeev, Akopyan, et al., 1973
Sergeev, Yu.L.; Akopyan, M.E.; Vilesov, F.I.; Chizhov, Yu.V.,
Photoionization processes in gaseous cyclohexane, and chloro- and bromocyclohexane,
High Energy Chem., 1973, 7, 369, In original 418. [all data]
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Notes
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- Symbols used in this document:
AE Appearance energy Cp,gas Constant pressure heat capacity of gas IE (evaluated) Recommended ionization energy S°gas Entropy of gas at standard conditions T Temperature ΔfH°gas Enthalpy of formation of gas at standard conditions ΔrG° Free energy of reaction at standard conditions ΔrH° Enthalpy of reaction at standard conditions ΔrS° Entropy of reaction at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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