Cyclohexylamine
- Formula: C6H13N
- Molecular weight: 99.1741
- IUPAC Standard InChIKey: PAFZNILMFXTMIY-UHFFFAOYSA-N
- CAS Registry Number: 108-91-8
- 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. - Other names: Cyclohexanamine; Aminocyclohexane; Aminohexahydrobenzene; Benzenamine, hexahydro-; Hexahydroaniline; Hexahydrobenzenamine; Aniline, hexahydro-; CHA; UN 2357; 1-Aminocyclohexane; 1-Cyclohexylamine
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Phase change data
Go To: Top, Gas phase ion energetics data, Gas Chromatography, 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
DRB - Donald R. Burgess, Jr.
AC - William E. Acree, Jr., James S. Chickos
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tboil | 407. ± 2. | K | AVG | N/A | Average of 6 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 252. | K | N/A | White and Bishop, 1940 | Uncertainty assigned by TRC = 4. K; TRC |
Tfus | 255.4 | K | N/A | Van de Vloed, 1939 | Uncertainty assigned by TRC = 0.7 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Tc | 614.6 | K | N/A | Majer and Svoboda, 1985 | |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 43.7 | kJ/mol | N/A | Majer and Svoboda, 1985 | |
ΔvapH° | 42.8 | kJ/mol | N/A | Steele, 1979 | DRB |
ΔvapH° | 42.8 ± 0.1 | kJ/mol | C | Bergstr«65533»m and Olofsson, 1975 | AC |
Enthalpy of vaporization
ΔvapH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
36.14 | 407.1 | N/A | Majer and Svoboda, 1985 | |
40.6 | 378. | N/A | Stephenson and Malanowski, 1987 | Based on data from 363. to 407. K.; AC |
40.8 | 348. | A | Stephenson and Malanowski, 1987 | Based on data from 333. to 408. K. See also Dykyj, 1972.; AC |
42.7 ± 0.1 | 313. | C | Majer, Svoboda, et al., 1979 | AC |
40.7 ± 0.1 | 343. | C | Majer, Svoboda, et al., 1979 | AC |
39.6 ± 0.1 | 358. | C | Majer, Svoboda, et al., 1979 | AC |
40.8 | 349. | N/A | Novák, Matous, et al., 1960 | Based on data from 334. to 401. K. See also Boublik, Fried, et al., 1984 and Novák, Matous, et al., 1960, 2.; AC |
Enthalpy of vaporization
ΔvapH =
A exp(-βTr) (1 − Tr)β
ΔvapH =
Enthalpy of vaporization (at saturation pressure)
(kJ/mol)
Tr = reduced temperature (T / Tc)
View plot Requires a JavaScript / HTML 5 canvas capable browser.
Temperature (K) | A (kJ/mol) | β | Tc (K) | Reference | Comment |
---|---|---|---|---|---|
313. to 358. | 62.78 | 0.3158 | 614.6 | Majer and Svoboda, 1985 |
Antoine Equation Parameters
log10(P) = A − (B / (T + C))
P = vapor pressure (bar)
T = temperature (K)
View plot Requires a JavaScript / HTML 5 canvas capable browser.
Temperature (K) | A | B | C | Reference | Comment |
---|---|---|---|---|---|
333.87 to 401.52 | 4.06885 | 1380.225 | -67.285 | Novák, Matous, et al., 1960 | Coefficents calculated by NIST from author's data. |
Enthalpy of fusion
ΔfusH (kJ/mol) | Temperature (K) | Reference | Comment |
---|---|---|---|
16.5 | 255.1 | Hamann and Würflinger, 1999 | AC |
14.92 | 255.4 | Van de Vloed, 1939 | See also Kabo, Kozyro, et al., 1999.; AC |
Gas phase ion energetics data
Go To: Top, Phase change data, Gas Chromatography, 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
Data compiled as indicated in comments:
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Proton affinity (review) | 934.4 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
Quantity | Value | Units | Method | Reference | Comment |
Gas basicity | 899.6 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
8.4 | PE | Aue and Bowers, 1979 | LLK |
8.4 ± 0.1 | PE | Aue, Webb, et al., 1976 | LLK |
8.86 | PE | Al-Joboury and Turner, 1964 | RDSH |
Gas Chromatography
Go To: Top, 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
Kovats' RI, non-polar column, isothermal
Column type | Active phase | Temperature (C) | I | Reference | Comment |
---|---|---|---|---|---|
Packed | Apolane | 130. | 863. | Dutoit, 1991 | Column length: 3.7 m |
Packed | SE-30 | 180. | 857. | Oszczapowicz, Osek, et al., 1985 | N2, Chromosorb A AW; Column length: 3. m |
Packed | SE-30 | 180. | 857. | Oszczapowicz, Osek, et al., 1984 | N2, Chromosorb W AW; Column length: 3. m |
Kovats' RI, polar column, isothermal
Column type | Active phase | Temperature (C) | I | Reference | Comment |
---|---|---|---|---|---|
Packed | PEG-2000 | 150. | 1257. | Anderson, Jurel, et al., 1973 | He, Celite 545 (44-60 mesh); Column length: 3. m |
Packed | PEG-2000 | 152. | 1230. | Anderson, Jurel, et al., 1973 | He, Celite 545 (44-60 mesh); Column length: 3. m |
Packed | PEG-2000 | 179. | 1251. | Anderson, Jurel, et al., 1973 | He, Celite 545 (44-60 mesh); Column length: 3. m |
Packed | PEG-2000 | 180. | 1267. | Anderson, Jurel, et al., 1973 | He, Celite 545 (44-60 mesh); Column length: 3. m |
Packed | PEG-2000 | 200. | 1265. | Anderson, Jurel, et al., 1973 | He, Celite 545 (44-60 mesh); Column length: 3. m |
Van Den Dool and Kratz RI, non-polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | DB-1 | 857. | Bartelt, 1997 | 30. m/0.32 mm/5. μm, He, 35. C @ 1. min, 10. K/min; Tend: 270. C |
Packed | SE-30 | 862. | Buchman, Cao, et al., 1984 | He, Chromosorb AW, 40. C @ 10. min, 10. K/min, 210. C @ 30. min; Column length: 3.05 m |
Van Den Dool and Kratz RI, non-polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | Methyl Silicone | 851. | Peng, Yang, et al., 1991 | Program: not specified |
Normal alkane RI, non-polar column, isothermal
Column type | Active phase | Temperature (C) | I | Reference | Comment |
---|---|---|---|---|---|
Capillary | Methyl Silicone | 100. | 855. | Lebrón-Aguilar, Quintanilla-López, et al., 2007 | |
Capillary | Methyl Silicone | 120. | 862. | Lebrón-Aguilar, Quintanilla-López, et al., 2007 | |
Capillary | Methyl Silicone | 140. | 870. | Lebrón-Aguilar, Quintanilla-López, et al., 2007 | |
Capillary | Methyl Silicone | 80. | 848. | Lebrón-Aguilar, Quintanilla-López, et al., 2007 |
Normal alkane RI, non-polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | OV-101 | 851. | Zenkevich, 2005 | 25. m/0.20 mm/0.10 μm, N2/He, 6. K/min; Tstart: 50. C; Tend: 250. C |
Normal alkane RI, polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | DB-Wax | 1222. | Peng, Yang, et al., 1991, 2 | Program: not specified |
References
Go To: Top, Phase change data, Gas phase ion energetics data, Gas Chromatography, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
White and Bishop, 1940
White, A.H.; Bishop, W.S.,
Dielectric Evidence of Molecular Rotation in the Crystals of Certain Non-aromatic Compounds,
J. Am. Chem. Soc., 1940, 62, 8-16. [all data]
Van de Vloed, 1939
Van de Vloed, A.,
Bull. Soc. Chim. Belg., 1939, 48, 229. [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]
Steele, 1979
Steele, W.V.,
The standard enthalpies of formation of cyclohexylamine and cyclohexylamine hydrochloride,
J. Chem. Thermodyn., 1979, 11, 1185-1188. [all data]
Bergstr«65533»m and Olofsson, 1975
Bergstr«65533»m, Stina; Olofsson, Gerd,
Thermodynamic quantities for the solution and protonation of four C6-amines in water over a wide temperature range,
J Solution Chem, 1975, 4, 7, 535-554, https://doi.org/10.1007/BF00643377
. [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]
Dykyj, 1972
Dykyj, J.,
Petrochemia, 1972, 12, 1, 13. [all data]
Majer, Svoboda, et al., 1979
Majer, Vladimír; Svoboda, Václav; Koubek, Josef; Pick, Jirí,
Temperature dependence of heats of vaporization, saturated vapour pressures and cohesive energies for a group of amines,
Collect. Czech. Chem. Commun., 1979, 44, 12, 3521-3528, https://doi.org/10.1135/cccc19793521
. [all data]
Novák, Matous, et al., 1960
Novák, J.; Matous, J.; Pick, J.,
Gleichgewicht flüssigkeit-dampf XXIV. Gleichgewicht flüssigkeit-dampf im system cyclohexylamin-cyclohexanol-anilin,
Collect. Czech. Chem. Commun., 1960, 25, 9, 2405-2413, https://doi.org/10.1135/cccc19602405
. [all data]
Boublik, Fried, et al., 1984
Boublik, T.; Fried, V.; Hala, E.,
The Vapour Pressures of Pure Substances: Selected Values of the Temperature Dependence of the Vapour Pressures of Some Pure Substances in the Normal and Low Pressure Region, 2nd ed., Elsevier, New York, 1984, 972. [all data]
Novák, Matous, et al., 1960, 2
Novák, J.; Matous, J.; Pick, J.,
Dampfdruck des cyclohexanols und des cyclohexylamins,
Collect. Czech. Chem. Commun., 1960, 25, 2, 583-585, https://doi.org/10.1135/cccc19600583
. [all data]
Hamann and Würflinger, 1999
Hamann, F.; Würflinger, A.,
DTA Measurements on Fluoro- and Amino-cyclohexane under High Pressure,
Zeitschrift für Physikalische Chemie, 1999, 211, Part1, 85-89, https://doi.org/10.1524/zpch.1999.211.Part1.085
. [all data]
Kabo, Kozyro, et al., 1999
Kabo, G.J.; Kozyro, A.A.; Frenkel, M.; Blokhin, A.V.,
Solid Phase Transitions of the Cyclohexane Derivatives and the Model of Energy States of Molecules in Plastic Crystals,
Molecular Crystals and Liquid Crystals Science and Technology. Section A. Molecular Crystals and Liquid Crystals, 1999, 326, 1, 333-355, https://doi.org/10.1080/10587259908025424
. [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]
Aue and Bowers, 1979
Aue, D.H.; Bowers, M.T.,
Chapter 9. Stabilities of positive ions from equilibrium gas phase basicity measurements
in Ions Chemistry,, ed. M.T. Bowers, 1979. [all data]
Aue, Webb, et al., 1976
Aue, D.H.; Webb, H.M.; Bowers, M.T.,
Quantitative proton affinities, ionization potentials, and hydrogen affinities of alkylamines,
J. Am. Chem. Soc., 1976, 98, 311. [all data]
Al-Joboury and Turner, 1964
Al-Joboury, M.I.; Turner, D.W.,
Molecular photoelectron spectroscopy. Part II. A summary of ionization potentials,
J. Chem. Soc., 1964, 4434. [all data]
Dutoit, 1991
Dutoit, J.,
Gas chromatographic retention behaviour of some solutes on structurally similar polar and non-polar stationary phases,
J. Chromatogr., 1991, 555, 1-2, 191-204, https://doi.org/10.1016/S0021-9673(01)87179-X
. [all data]
Oszczapowicz, Osek, et al., 1985
Oszczapowicz, J.; Osek, J.; Ciszkowski, K.; Krawczyk, W.; Ostrowski, M.,
Retention Indices of Dimethylbenzamidines and Benzylideneamines on a Non-Polar Column,
J. Chromatogr., 1985, 330, 79-85, https://doi.org/10.1016/S0021-9673(01)81964-6
. [all data]
Oszczapowicz, Osek, et al., 1984
Oszczapowicz, J.; Osek, J.; Dolecka, E.,
Retention indices of dimethylformamidines, dimethylacetamidines and tetramethylguanidines on a non-polar column,
J. Chromatogr., 1984, 315, 95-100, https://doi.org/10.1016/S0021-9673(01)90727-7
. [all data]
Anderson, Jurel, et al., 1973
Anderson, A.; Jurel, S.; Shymanska, M.; Golender, L.,
Gas-liquid chromatography of some aliphatic and heterocyclic mono- and pollyfunctional amines. VII. Retention indices of amines in some polar and unpolar stationary phases,
Latv. PSR Zinat. Akad. Vestis Kim. Ser., 1973, 1, 51-63. [all data]
Bartelt, 1997
Bartelt, R.J.,
Calibration of a commercial solid-phase microextraction device for measuring headspace concentrations of organic volatiles,
Anal. Chem., 1997, 69, 3, 364-372, https://doi.org/10.1021/ac960820n
. [all data]
Buchman, Cao, et al., 1984
Buchman, O.; Cao, G.-Y.; Peng, C.T.,
Structure assignment by retention index in gas-liquid radiochromatography of substituted cyclohexenes,
J. Chromatogr., 1984, 312, 75-90, https://doi.org/10.1016/S0021-9673(01)92765-7
. [all data]
Peng, Yang, et al., 1991
Peng, C.T.; Yang, Z.C.; Maltby, D.,
Prediction of retention indexes. III. Silylated derivatives of polar compounds,
J. Chromatogr., 1991, 586, 1, 113-129, https://doi.org/10.1016/0021-9673(91)80029-G
. [all data]
Lebrón-Aguilar, Quintanilla-López, et al., 2007
Lebrón-Aguilar, R.; Quintanilla-López, J.E.; Tello, A.M.; Santiuste, J.M.,
Isothermal retention indices on poly (3,3,3-trifluoropropylmethylsiloxane) stationary phases,
J. Chromatogr. A, 2007, 1160, 1-2, 276-288, https://doi.org/10.1016/j.chroma.2007.05.025
. [all data]
Zenkevich, 2005
Zenkevich, I.G.,
Experimentally measured retention indices., 2005. [all data]
Peng, Yang, et al., 1991, 2
Peng, C.T.; Yang, Z.C.; Ding, S.F.,
Prediction of rentention idexes. II. Structure-retention index relationship on polar columns,
J. Chromatogr., 1991, 586, 1, 85-112, https://doi.org/10.1016/0021-9673(91)80028-F
. [all data]
Notes
Go To: Top, Phase change data, Gas phase ion energetics data, Gas Chromatography, References
- Symbols used in this document:
Tboil Boiling point Tc Critical temperature Tfus Fusion (melting) point ΔfusH Enthalpy 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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