1-Octanamine
- Formula: C8H19N
- Molecular weight: 129.2432
- IUPAC Standard InChIKey: IOQPZZOEVPZRBK-UHFFFAOYSA-N
- CAS Registry Number: 111-86-4
- 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: Octylamine; n-Octylamine; Armeen 8; Caprylamine; Caprylylamine; 1-Aminooctane; 1-Octylamine; n-C8H17NH2; n-Octylamine, mono-; Monooctylamine; Octanamine; Amine 8D; Monoctylamine; NSC 9824
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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
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DRB - Donald R. Burgess, Jr.
AC - William E. Acree, Jr., James S. Chickos
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tboil | 452. ± 7. | K | AVG | N/A | Average of 9 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 272.75 | K | N/A | Zvejnieks, 1954 | Uncertainty assigned by TRC = 0.2 K; TRC |
Tfus | 273.15 | K | N/A | Hoffman and Smyth, 1949 | Uncertainty assigned by TRC = 0.5 K; TRC |
Tfus | 272.15 | K | N/A | Ralston, Hoerr, et al., 1942 | Uncertainty assigned by TRC = 0.5 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Tc | 641. | K | N/A | Steele, Chirico, et al., 1996 | Uncertainty assigned by TRC = 3. K; fitting parameter in Wagner equation for vapor pressure; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Pc | 25.83 | atm | N/A | Steele, Chirico, et al., 1996 | Uncertainty assigned by TRC = 3.95 atm; from extrapolation of obs. vapor pressure to Tc; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ρc | 1.93 | mol/l | N/A | Steele, Chirico, et al., 1996 | Uncertainty assigned by TRC = 0.23 mol/l; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 13.06 ± 0.23 | kcal/mol | V | Steele, Chirico, et al., 1996, 2 | ALS |
ΔvapH° | 13.0 | kcal/mol | N/A | Steele, Chirico, et al., 1996, 2 | DRB |
ΔvapH° | 13.1 ± 0.1 | kcal/mol | EB | Steele, Chirico, et al., 1996, 2 | Based on data from 343. to 494. K.; AC |
ΔvapH° | 13.0 | kcal/mol | CGC | Chickos, Hosseini, et al., 1995 | Based on data from 323. to 373. K.; AC |
Enthalpy of vaporization
ΔvapH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
12.1 | 323. | A | Stephenson and Malanowski, 1987 | Based on data from 308. to 453. K.; 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:
MM - Michael M. Meot-Ner (Mautner)
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Proton affinity (review) | 222.0 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
Quantity | Value | Units | Method | Reference | Comment |
Gas basicity | 213.9 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
Proton affinity at 298K
Proton affinity (kcal/mol) | Reference | Comment |
---|---|---|
221.1 | Wang, Chu, et al., 1999 | KM results obtained from CID of complexes with other primary amines at E(cm) = 0 eV, extrapolated from CID at E(cm) = 0.8, 1.5, 2.0 eV; MM |
221.0 | Wang, Chu, et al., 1999 | KM results obtained from CID of complexes with other primary amines using Fenselau/Wesdemiotis correction; MM |
Gas basicity at 298K
Gas basicity (review) (kcal/mol) | Reference | Comment |
---|---|---|
210.2 ± 2.2 | Gross, Rodriguez-Cruz, et al., 1995 | T = 300K; 3-Fluoropyridine; i-Propylamine. Reference GBs readjusted to Hunter and Lias, 1998. Cited uncertainty is half of the ΔGB between the bracketing bases; MM |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
8.5 | PE | Aue and Bowers, 1979 | LLK |
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 | SE-30 | 170. | 993. | Voelkel, 1987 | He, Chromaton N Super (75-100 mesh); Column length: 1. m |
Packed | SE-30 | 180. | 1038. | Oszczapowicz, Osek, et al., 1985 | N2, Chromosorb A AW; Column length: 3. m |
Packed | Apiezon L | 100. | 1041. | Golovnya and Zhuravleva, 1973 | |
Packed | Apiezon L | 130. | 1022. | Landault and Guiochon, 1964 | Teflon-Haloport; Column length: 2.26 m |
Kovats' RI, polar column, isothermal
Column type | Active phase | Temperature (C) | I | Reference | Comment |
---|---|---|---|---|---|
Packed | PEG-2000 | 150. | 1320. | Anderson, Jurel, et al., 1973 | He, Celite 545 (44-60 mesh); Column length: 3. m |
Packed | PEG-2000 | 152. | 1320. | Anderson, Jurel, et al., 1973 | He, Celite 545 (44-60 mesh); Column length: 3. m |
Packed | PEG-2000 | 179. | 1318. | Anderson, Jurel, et al., 1973 | He, Celite 545 (44-60 mesh); Column length: 3. m |
Packed | PEG-2000 | 180. | 1317. | Anderson, Jurel, et al., 1973 | He, Celite 545 (44-60 mesh); Column length: 3. m |
Packed | PEG-2000 | 200. | 1315. | 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 | SE-54 | 1038. | Woolley, Markides, et al., 1986 | 20. m/0.05 mm/0.25 μm, He, 40. C @ 2. min, 4. K/min; Tend: 180. C |
Capillary | SE-54 | 1042. | Woolley, Markides, et al., 1986 | 20. m/0.05 mm/0.25 μm, He, 40. C @ 2. min, 4. K/min; Tend: 180. C |
Capillary | SE-54 | 1043. | Woolley, Markides, et al., 1986 | 20. m/0.05 mm/0.25 μm, He, 40. C @ 2. min, 4. K/min; Tend: 180. C |
Capillary | SE-54 | 1044. | Woolley, Markides, et al., 1986 | 20. m/0.05 mm/0.25 μm, He, 40. C @ 2. min, 4. K/min; Tend: 180. C |
Capillary | SE-54 | 1046. | Woolley, Markides, et al., 1986 | 20. m/0.05 mm/0.25 μm, He, 40. C @ 2. min, 4. K/min; Tend: 180. C |
Capillary | SE-54 | 1047. | Woolley, Markides, et al., 1986 | 20. m/0.05 mm/0.25 μm, He, 40. C @ 2. min, 4. K/min; Tend: 180. C |
Capillary | SE-54 | 1047. | Woolley, Markides, et al., 1986 | 20. m/0.05 mm/0.25 μm, He, 40. C @ 2. min, 4. K/min; Tend: 180. C |
Capillary | SE-54 | 1049. | Woolley, Markides, et al., 1986 | 20. m/0.05 mm/0.25 μm, He, 40. C @ 2. min, 4. K/min; Tend: 180. C |
Capillary | SE-54 | 1051. | Woolley, Markides, et al., 1986 | 20. m/0.05 mm/0.25 μm, He, 40. C @ 2. min, 4. K/min; Tend: 180. C |
Capillary | SE-54 | 1057. | Woolley, Markides, et al., 1986 | 20. m/0.05 mm/0.25 μm, He, 40. C @ 2. min, 4. K/min; Tend: 180. C |
Capillary | SE-54 | 1058. | Woolley, Markides, et al., 1986 | 20. m/0.05 mm/0.25 μm, He, 40. C @ 2. min, 4. K/min; Tend: 180. C |
Van Den Dool and Kratz RI, non-polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | DB-1 | 1032. | Peng, 2000 | 15. m/0.53 mm/1. μm, He; Program: 40C(3min) => 8C/min => 200(1min) => 5C/min => 300C(25min) |
Van Den Dool and Kratz RI, polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | HP-Wax | 1316. | Peng, 2000 | 15. m/0.53 mm/1. μm, He, 40. C @ 3. min, 5. K/min, 220. C @ 30. min |
Normal alkane RI, non-polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | Ultra-1 | 1028. | Okumura, 1991 | 25. m/0.32 mm/0.25 μm, He, 3. K/min; Tstart: 80. C; Tend: 260. C |
Normal alkane RI, non-polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | Methyl Silicone | 1041. | Chen and Feng, 2007 | 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.
Zvejnieks, 1954
Zvejnieks, A.,
Preparation and Properties of Some Pure Fatty and Rosin Amines.,
Sven. Kem. Tidskr., 1954, 66, 316. [all data]
Hoffman and Smyth, 1949
Hoffman, J.D.; Smyth, C.P.,
Molecular Freedom and Proton Transfer in Solid Long-Chain Amines.,
J. Am. Chem. Soc., 1949, 71, 3591. [all data]
Ralston, Hoerr, et al., 1942
Ralston, A.W.; Hoerr, C.W.; Hoffman, E.J.,
Studies on High Molecular Weight ALiphatic Amines and Their Salts. VII The Systems Octylamine, Dodecylamine, and Octadecylamine-Water,
J. Am. Chem. Soc., 1942, 64, 1516. [all data]
Steele, Chirico, et al., 1996
Steele, W.V.; Chirico, R.D.; Knipmeyer, S.E.; Nguyen, A.; Smith, N.K.; Tasker, I.R.,
Thermodynamic Properties and Ideal-Gas Enthalpies of Formation for Dioctylamine, trioctylamine, Phenyl Isocyanate, and 1,4,5,6-Tetrahydropyrimidine,
J. Chem. Eng. Data, 1996, 41, 1269-84. [all data]
Steele, Chirico, et al., 1996, 2
Steele, W.V.; Chirico, R.D.; Knipmeyer, S.E.; Nguyen, A.; Smith, N.K.; Tasker, I.R.,
Thermodynamic properties and ideal-gas enthalpies of formation for cyclohexene, phthalan (2,5-dihydrobenzo-3,4-furan), isoxazole, octylamine, dioctylamine, trioctylamine, phenyl isocyanate, and 1,4,5,6-tetrahydropyrimidine,
J. Chem. Eng. Data, 1996, 41, 1269-1284. [all data]
Chickos, Hosseini, et al., 1995
Chickos, James S.; Hosseini, Sarah; Hesse, Donald G.,
Determination of vaporization enthalpies of simple organic molecules by correlations of changes in gas chromatographic net retention times,
Thermochimica Acta, 1995, 249, 41-62, https://doi.org/10.1016/0040-6031(95)90670-3
. [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]
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]
Wang, Chu, et al., 1999
Wang, Z.; Chu, I.K.; Rodriquez, C.F.; Hopkinson, A.C.; Siu, K.W.M.,
α,ω-Diaminoalkanes as models for bases that dicoordinate the proton: An evaluation of the kinetic method for estimating their proton affinities,
J. Phys. Chem. A., 1999, 103, 8700. [all data]
Gross, Rodriguez-Cruz, et al., 1995
Gross, D.S.; Rodriguez-Cruz, S.E.; Bock, S.; Williams, E.R.,
Measurement of the Coulomb Energy and Dielectric Polarizability of Gas-Phase Diprotonated Diaminoalkanes,
J. Phys. Chem., 1995, 99, 4034. [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]
Voelkel, 1987
Voelkel, A.,
Retention Indices and Thermodynamic Functions of Solution for Model Non-Ionic Surfactants in Standard Stationary Phases Determined by Gas Chromatography,
J. Chromatogr., 1987, 387, 95-104, https://doi.org/10.1016/S0021-9673(01)94516-9
. [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]
Golovnya and Zhuravleva, 1973
Golovnya, R.V.; Zhuravleva, I.L.,
Gas Chromatographic Method of Identification of n-Aliphatic Amines Through the Use of Donor-Acceptor Interaction with Phosphate,
Chromatographia, 1973, 6, 12, 508-513, https://doi.org/10.1007/BF02269131
. [all data]
Landault and Guiochon, 1964
Landault, C.; Guiochon, G.,
Separation des amines par chromatographie gaz-liquide en utilisant le teflon comme support,
J. Chromatogr., 1964, 13, 327-336, https://doi.org/10.1016/S0021-9673(01)95126-X
. [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]
Woolley, Markides, et al., 1986
Woolley, C.L.; Markides, K.E.; Lee, M.L.; Bartle, K.D.,
Deactivation of small diameter fused silica capillary columns with organosilicon hydrides,
J. Hi. Res. Chromatogr. Chromatogr. Comm., 1986, 9, 9, 506-514, https://doi.org/10.1002/jhrc.1240090904
. [all data]
Peng, 2000
Peng, C.T.,
Prediction of retention indices. V. Influence of electronic effects and column polarity on retention index,
J. Chromatogr. A, 2000, 903, 1-2, 117-143, https://doi.org/10.1016/S0021-9673(00)00901-8
. [all data]
Okumura, 1991
Okumura, T.,
retention indices of environmental chemicals on methyl silicone capillary column,
Journal of Environmental Chemistry (Japan), 1991, 1, 2, 333-358, https://doi.org/10.5985/jec.1.333
. [all data]
Chen and Feng, 2007
Chen, Y.; Feng, C.,
QSPR study on gas chromatography retention index of some organic pollutants,
Comput. Appl. Chem. (China), 2007, 24, 10, 1404-1408. [all data]
Notes
Go To: Top, Phase change data, Gas phase ion energetics data, Gas Chromatography, References
- Symbols used in this document:
Pc Critical pressure Tboil Boiling point Tc Critical temperature Tfus Fusion (melting) point 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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