1-Butanamine, N-butyl-
- Formula: C8H19N
- Molecular weight: 129.2432
- IUPAC Standard InChIKey: JQVDAXLFBXTEQA-UHFFFAOYSA-N
- CAS Registry Number: 111-92-2
- 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: Dibutylamine; Di-n-butylamine; N-Dibutylamine; (n-C4H9)2NH; n-Butyl-1-butanamine; di-Normal-butylamine; Dibutilamina; UN 2248; Butylamine, di-n-
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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, Ion clustering 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
DRB - Donald R. Burgess, Jr.
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°gas | -40.89 ± 0.76 | kcal/mol | Ccb | Suradi, Hacking, et al., 1981 | ALS |
ΔfH°gas | -39.41 | kcal/mol | N/A | Lebedeva, Katin, et al., 1971 | Value computed using ΔfHliquid° value of -206.1±0.4 kj/mol from Lebedeva, Katin, et al., 1971 and ΔvapH° value of 41.2 kj/mol from Suradi, Hacking, et al., 1981.; DRB |
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 by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°liquid | -50.74 ± 0.60 | kcal/mol | Ccb | Suradi, Hacking, et al., 1981 | |
ΔfH°liquid | -49.27 ± 0.09 | kcal/mol | Ccb | Lebedeva, Katin, et al., 1971 | |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°liquid | -1350.7 ± 0.53 | kcal/mol | Ccb | Suradi, Hacking, et al., 1981 | |
ΔcH°liquid | -1352.16 ± 0.10 | kcal/mol | Ccb | Lebedeva, Katin, et al., 1971 |
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
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 | 430. ± 20. | K | AVG | N/A | Average of 9 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 211.25 | K | N/A | Timmermans, 1952 | Uncertainty assigned by TRC = 0.5 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Tc | 595.8 | K | N/A | Majer and Svoboda, 1985 | |
Tc | 607.5 | K | N/A | Toczylkin. L.S. and Young, 1980 | Uncertainty assigned by TRC = 0.6 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Pc | 30.69 | atm | N/A | Toczylkin. L.S. and Young, 1980 | Uncertainty assigned by TRC = 0.3066 atm; Visual; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 11. ± 2. | kcal/mol | AVG | N/A | Average of 7 values; Individual data points |
Enthalpy of vaporization
ΔvapH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
9.187 | 432.8 | N/A | Majer and Svoboda, 1985 | |
11.0 | 358. | A | Stephenson and Malanowski, 1987 | Based on data from 343. to 479. K.; AC |
11.0 ± 0.02 | 343. | C | Petros, Majer, et al., 1979 | AC |
10.7 ± 0.02 | 358. | C | Petros, Majer, et al., 1979 | AC |
11.5 | 291. | V | Lebedeva, Katin, et al., 1971 | ALS |
Enthalpy of vaporization
ΔvapH =
A exp(-βTr) (1 − Tr)β
ΔvapH =
Enthalpy of vaporization (at saturation pressure)
(kcal/mol)
Tr = reduced temperature (T / Tc)
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Temperature (K) | A (kcal/mol) | β | Tc (K) | Reference | Comment |
---|---|---|---|---|---|
298. to 358. | 17.00 | 0.3042 | 595.8 | Majer and Svoboda, 1985 |
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 as indicated in comments:
M - Michael M. Meot-Ner (Mautner) and Sharon G. Lias
ALS - 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: C3H9Sn+ + C8H19N = (C3H9Sn+ • C8H19N)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 48.8 | kcal/mol | PHPMS | Stone and Splinter, 1984 | gas phase; switching reaction((CH3)3Sn+)CH3OH, Entropy change calculated or estimated; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 33.7 | cal/mol*K | N/A | Stone and Splinter, 1984 | gas phase; switching reaction((CH3)3Sn+)CH3OH, Entropy change calculated or estimated; M |
Free energy of reaction
ΔrG° (kcal/mol) | T (K) | Method | Reference | Comment |
---|---|---|---|---|
31.1 | 525. | PHPMS | Stone and Splinter, 1984 | gas phase; switching reaction((CH3)3Sn+)CH3OH, Entropy change calculated or estimated; M |
+
= C15H23N3O3
By formula: C7H4N2O3 + C8H19N = C15H23N3O3
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -27.2 ± 0.2 | kcal/mol | Cm | Kiselev, Malkov, et al., 1989 | liquid phase; solvent: Dioxane; #TDE; ALS |
+
= C16H16N2O
By formula: C8H19N + C8H7NO = C16H16N2O
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -24.5 ± 0.2 | kcal/mol | Cm | Kiselev, Malkov, et al., 1989 | liquid phase; solvent: Chlorobenzene; ALS |
By formula: H2 + C8H17N = C8H19N
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 20.6 ± 0.62 | kcal/mol | Chyd | Hafelinger and Steinmann, 1977 | liquid phase; solvent: Acetic acid; ALS |
By formula: C7H5NO + C8H19N = C15H24N2O
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -260.23 ± 0.41 | kcal/mol | Cm | Kiselev, Malkov, et al., 1989 | liquid phase; solvent: Dioxane; ALS |
+
= C16H26N2O
By formula: C8H19N + C8H7NO = C16H26N2O
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -24.7 ± 0.2 | kcal/mol | Cm | Kiselev, Malkov, et al., 1989 | liquid phase; solvent: Dioxane; ALS |
+
= C16H26N2O
By formula: C8H19N + C8H7NO = C16H26N2O
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -23.0 ± 0.2 | kcal/mol | Cm | Kiselev, Malkov, et al., 1989 | liquid phase; solvent: Dioxane; ALS |
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 evaluated as indicated in comments:
HL - Edward P. Hunter and Sharon G. Lias
Data compiled as indicated in comments:
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Proton affinity (review) | 231.5 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
Quantity | Value | Units | Method | Reference | Comment |
Gas basicity | 223.5 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
7.69 ± 0.03 | PI | Watanabe and Mottl, 1957 | RDSH |
Ion clustering data
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, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Data compiled by: Michael M. Meot-Ner (Mautner) and Sharon G. Lias
Note: Please consider using the reaction search for this species. This page allows searching of all reactions involving this species. Searches may be limited to ion clustering reactions. A general reaction search form is also available.
Clustering reactions
By formula: C3H9Sn+ + C8H19N = (C3H9Sn+ • C8H19N)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 48.8 | kcal/mol | PHPMS | Stone and Splinter, 1984 | gas phase; switching reaction((CH3)3Sn+)CH3OH, Entropy change calculated or estimated |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 33.7 | cal/mol*K | N/A | Stone and Splinter, 1984 | gas phase; switching reaction((CH3)3Sn+)CH3OH, Entropy change calculated or estimated |
Free energy of reaction
ΔrG° (kcal/mol) | T (K) | Method | Reference | Comment |
---|---|---|---|---|
31.1 | 525. | PHPMS | Stone and Splinter, 1984 | gas phase; switching reaction((CH3)3Sn+)CH3OH, Entropy change calculated or estimated |
IR Spectrum
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering data, Mass spectrum (electron ionization), References, Notes
Data compiled by: Coblentz Society, Inc.
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, Ion clustering 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 | Japan AIST/NIMC Database- Spectrum MS-NW-8462 |
NIST MS number | 228624 |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering 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.
Suradi, Hacking, et al., 1981
Suradi, S.; Hacking, J.M.; Pilcher, G.; Gumrukcu, I.; Lappert, M.F.,
Enthalpies of combustion of five sterically hindered amines,
J. Chem. Thermodyn., 1981, 13, 857-861. [all data]
Lebedeva, Katin, et al., 1971
Lebedeva, N.D.; Katin, Y.A.; Akhmedova, G.Y.,
Enthalpies of formation of dipropylamine, di-isopropylamine, dibutylamine, and di-isobutylamine,
Russ. J. Phys. Chem. (Engl. Transl.), 1971, 45, 771-772. [all data]
Timmermans, 1952
Timmermans, J.,
Freezing points of organic compounds. VVI New determinations.,
Bull. Soc. Chim. Belg., 1952, 61, 393. [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]
Toczylkin. L.S. and Young, 1980
Toczylkin. L.S.; Young, C.L.,
Gas-liquid criticl temperatures of mixtures containing electron donors. II. Amine mixtures,
J. Chem. Thermodyn., 1980, 12, 365. [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]
Petros, Majer, et al., 1979
Petros, Libor; Majer, Vladimír; Koubek, Josef; Svoboda, Václav; Pick, Jirí,
Temperature dependence of heats of vaporization, saturated vapour pressures and cohesive energies of secondary amines,
Collect. Czech. Chem. Commun., 1979, 44, 12, 3533-3540, https://doi.org/10.1135/cccc19793533
. [all data]
Stone and Splinter, 1984
Stone, J.A.; Splinter, D.E.,
A high-pressure mass spectrometric study of the binding of (CH3)3Sn+ to lewis bases in the gas phase,
Int. J. Mass Spectrom. Ion Processes, 1984, 59, 169. [all data]
Kiselev, Malkov, et al., 1989
Kiselev, V.D.; Malkov, V.B.; Murzin, D.G.; Shakirov, I.M.; Konovalov, A.I.,
Thermochemical study of the reaction of isocyanate with amines,
Dokl. Phys. Chem. (Engl. Transl.), 1989, 308, 711-713, In original 111. [all data]
Hafelinger and Steinmann, 1977
Hafelinger, G.; Steinmann, L.,
Heat of hydrogenation of compounds containing isolated and conjugted C=N bouble bonds,
Angew. Chem. Int. Ed. Engl., 1977, 16, 47-48. [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]
Watanabe and Mottl, 1957
Watanabe, K.; Mottl, J.R.,
Ionization potentials of ammonia and some amines,
J. Chem. Phys., 1957, 26, 1773. [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, Ion clustering data, IR Spectrum, Mass spectrum (electron ionization), References
- Symbols used in this document:
Pc Critical pressure T Temperature Tboil Boiling point Tc Critical temperature Tfus Fusion (melting) point 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 ΔrG° Free energy of reaction at standard conditions ΔrH° Enthalpy of reaction at standard conditions ΔrS° Entropy 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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