n-Butyl ether
- Formula: C8H18O
- Molecular weight: 130.2279
- IUPAC Standard InChIKey: DURPTKYDGMDSBL-UHFFFAOYSA-N
- CAS Registry Number: 142-96-1
- 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: Butane, 1,1'-oxybis-; Butyl ether; n-Dibutyl ether; Di-n-butyl ether; Dibutyl ether; Dibutyl oxide; 1,1'-Oxybis(butane); (n-C4H9)2O; 1-Butoxybutane; Butyl oxide; Ether butylique; UN 1149; NSC 8459
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Condensed 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:
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 | -90.34 ± 0.24 | kcal/mol | Ccb | Colomina, Pell, et al., 1965 | ALS |
ΔfH°liquid | -90.24 ± 0.66 | kcal/mol | Ccb | Murrin and Goldhagen, 1957 | ALS |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°liquid | -1276.92 ± 0.22 | kcal/mol | Ccb | Colomina, Pell, et al., 1965 | Corresponding ΔfHºliquid = -90.32 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS |
ΔcH°liquid | -1277.03 ± 0.66 | kcal/mol | Ccb | Murrin and Goldhagen, 1957 | Corresponding ΔfHºliquid = -90.21 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS |
ΔcH°liquid | -1277.10 ± 0.80 | kcal/mol | Ccb | Skuratov, Strepikheev, et al., 1957 | Reanalyzed by Cox and Pilcher, 1970, Original value = -1277.5 ± 0.8 kcal/mol; Combustion at 293 K; Corresponding ΔfHºliquid = -90.14 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS |
Constant pressure heat capacity of liquid
Cp,liquid (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
66.482 | 298.15 | Cobos, Casanova, et al., 1987 | Average of two measurements.; DH |
Reaction thermochemistry data
Go To: Top, Condensed 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 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. 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: CH6N+ + C8H18O = (CH6N+ • C8H18O)
Bond type: Hydrogen bonds of the type NH+-O between organics
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 25.0 | kcal/mol | PHPMS | Meot-Ner, 1984 | gas phase |
ΔrH° | 25.0 | kcal/mol | PHPMS | Meot-Ner (Mautner), 1983 | gas phase |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 28.0 | cal/mol*K | PHPMS | Meot-Ner, 1984 | gas phase |
ΔrS° | 28.0 | cal/mol*K | PHPMS | Meot-Ner (Mautner), 1983 | gas phase |
Gas phase ion energetics data
Go To: Top, Condensed 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
Data compiled as indicated in comments:
MM - Michael M. Meot-Ner (Mautner)
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) | 202.1 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
Quantity | Value | Units | Method | Reference | Comment |
Gas basicity | 195.6 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
Gas basicity at 298K
Gas basicity (review) (kcal/mol) | Reference | Comment |
---|---|---|
194.9 ± 0.1 | Decouzon, Gal, et al., 1996 | T = 338K; MM |
194.9 ± 0.1 | Decouzon, Gal, et al., 1996 | T = 338K; MM |
195.1 | Decouzon, Gal, et al., 1996 | T = T(eff) = 430K; MM |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
9.28 ± 0.05 | EI | Williams and Hamill, 1968 | RDSH |
9.44 | PE | Aue and Bowers, 1979 | Vertical value; LLK |
9.40 | PE | Benoit and Harrison, 1977 | Vertical value; LLK |
9.51 ± 0.015 | PE | Klessinger, Asmus, et al., 1975 | Vertical value; LLK |
Appearance energy determinations
Ion | AE (eV) | Other Products | Method | Reference | Comment |
---|---|---|---|---|---|
C4H9+ | 11.8 ± 0.1 | ? | EI | Williams and Hamill, 1968 | RDSH |
C4H9O+ | 13.0 ± 0.1 | C4H9 | EI | Williams and Hamill, 1968 | RDSH |
References
Go To: Top, Condensed 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.
Colomina, Pell, et al., 1965
Colomina, M.; Pell, A.S.; Skinner, H.A.; Coleman, D.J.,
Heats of combustion of four dialkylethers,
Trans. Faraday Soc., 1965, 61, 2641. [all data]
Murrin and Goldhagen, 1957
Murrin, J.W.; Goldhagen, S.,
Determination of the C-O bond energy from the heats of combustion of four aliphatic ethers,
NAVORD Report No. 5491, U.S. Naval Powder Factory Res. & Dev. Dept., 1957, 1-14. [all data]
Skuratov, Strepikheev, et al., 1957
Skuratov, S.M.; Strepikheev, A.A.; Kozina, M.P.,
About the reaction activity of five and six-membered heterocyclic compounds,
Dokl. Akad. Nauk SSSR, 1957, 117, 452-454. [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]
Cobos, Casanova, et al., 1987
Cobos, J.C.; Casanova, C.; Roux-Desgranges, G.; Grolier, J.-P.E.,
Excess properties of mixtures of some n-alkoxyethanols with organic solvents. II. VEm and CEp,m with di-n-butylether at 298.15 K,
J. Chem. Thermodynam., 1987, 19, 791-796. [all data]
Meot-Ner, 1984
Meot-Ner, (Mautner)M.,
The Ionic Hydrogen Bond and Ion Solvation. 1. -NH+ O-, -NH+ N- and -OH+ O- Bonds. Correlations with Proton Affinity. Deviations Due to Structural Effects,
J. Am. Chem. Soc., 1984, 106, 5, 1257, https://doi.org/10.1021/ja00317a015
. [all data]
Meot-Ner (Mautner), 1983
Meot-Ner (Mautner), M.,
The Ionic Hydrogen Bond. 3. Multiple and -CH+...O- Bonds. Complexes of Ammonium Ions with Polyethers and Crown Ethers,
J. Am. Chem. Soc., 1983, 105, 15, 4912, https://doi.org/10.1021/ja00353a012
. [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]
Decouzon, Gal, et al., 1996
Decouzon, M.; Gal, J.E.; Herreros, M.; Marai, P.C.; Murrell, J.; Todd, J.F.J.,
On the Use of the Kinetic Method for the Determination of Proton Affinities by Fourier-Transfrom Ion Cyclotron Resonance Mass Spectrometry,
Rapid. Comm. Mass Spectrom., 1996, 10, 242. [all data]
Williams and Hamill, 1968
Williams, J.M.; Hamill, W.H.,
Ionization potentials of molecules and free radicals and appearance potentials by electron impact in the mass spectrometer,
J. Chem. Phys., 1968, 49, 4467. [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]
Benoit and Harrison, 1977
Benoit, F.M.; Harrison, A.G.,
Predictive value of proton affinity. Ionization energy correlations involving oxygenated molecules,
J. Am. Chem. Soc., 1977, 99, 3980. [all data]
Klessinger, Asmus, et al., 1975
Klessinger, M.; Asmus, P.; Kraatz, U.,
Photoelektronenspektren organischer verbindungen-VII,
Tetrahedron, 1975, 31, 517. [all data]
Notes
Go To: Top, Condensed phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, References
- Symbols used in this document:
AE Appearance energy Cp,liquid Constant pressure heat capacity of liquid ΔcH°liquid Enthalpy of combustion of liquid at standard conditions ΔfH°liquid Enthalpy of formation of liquid 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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