Ethyl ether

Formula: C₄H₁₀O
Molecular weight: 74.1216
IUPAC Standard InChI: InChI=1S/C4H10O/c1-3-5-4-2/h3-4H2,1-2H3
IUPAC Standard InChIKey: RTZKZFJDLAIYFH-UHFFFAOYSA-N
CAS Registry Number: 60-29-7
Chemical structure:
This structure is also available as a 2d Mol file or as a computed 3d SD file
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Other names: Ethane, 1,1'-oxybis-; Anaesthetic ether; Anesthesia ether; Anesthetic ether; Diethyl ether; Diethyl oxide; Ethoxyethane; Pronarcol; Solvent ether; 1,1'-Oxybisethane; (C2H5)2O; Aether; Diaethylaether; Dwuetylowy eter; Etere etilico; Ether ethylique; Ether, ethyl; Ethyl ether, tech.; Ethyl oxide; Oxyde d'ethyle; Rcra waste number U117; UN 1155; 3-Oxapentane; Ether; Ethyl ether anhydrous A.C.S.; Sulfuric ether; NSC 100036
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Gas phase thermochemistry data

Go To: Top, Condensed phase thermochemistry data, Gas phase ion energetics data, References, Notes

Data compiled as indicated in comments:
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
Δ_fH°_gas	-60.40 ± 0.47	kcal/mol	Ccb	Pihlaja and Heikkil, 1968	Reanalyzed by Pedley, Naylor, et al., 1986, Original value = -59.82 ± 0.44 kcal/mol; ALS
Δ_fH°_gas	-60.28 ± 0.19	kcal/mol	Cm	Pilcher, Skinner, et al., 1963	ALS
Δ_fH°_gas	-58.4	kcal/mol	Ccb	Murrin and Goldhagen, 1957	ALS
Quantity	Value	Units	Method	Reference	Comment
Δ_cH°_gas	-651.60 ± 0.43	kcal/mol	Ccb	Pihlaja and Heikkil, 1968	Corresponding Δ_fHº_gas = -66.18 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS
Δ_cH°_gas	-657.52 ± 0.18	kcal/mol	Cm	Pilcher, Skinner, et al., 1963	Corresponding Δ_fHº_gas = -60.26 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS
Quantity	Value	Units	Method	Reference	Comment
S°_gas	81.79	cal/mol*K	N/A	Counsell J.F., 1971	Other third-law entropy values at 298.15 K are 342.46 [ Cope C.S., 1959], 342.33 [ Stull D.R., 1969], and 342.60 J/mol*K [ Chao J., 1986].; GT

Constant pressure heat capacity of gas

C_p,gas (cal/mol*K)	Temperature (K)	Reference	Comment
14.94	100.	Chao J., 1986	p=1 bar.; GT
20.27	150.
23.83	200.
27.318	273.15
28.552 ± 0.036	298.15
28.647	300.
34.132	400.
39.620	500.
44.539	600.
48.841	700.
52.591	800.
55.865	900.
58.719	1000.
61.205	1100.
63.365	1200.
65.241	1300.
66.876	1400.
68.298	1500.

Constant pressure heat capacity of gas

C_p,gas (cal/mol*K)	Temperature (K)	Reference	Comment
29.144	309.98	Counsell J.F., 1971	Other experimental values of heat capacity [ Jennings W.H., 1934, Jatkar S.K.K., 1939, Valentin F.H.H., 1950] are believed to be less reliable (see [ Chao J., 1986]).; GT
30.251	329.99
31.386	350.00
32.794	375.00
34.242	400.01
35.636	424.99
37.072	450.04

Condensed phase thermochemistry data

Go To: Top, Gas phase thermochemistry data, Gas phase ion energetics data, References, Notes

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
Δ_fH°_liquid	-64.81 ± 0.45	kcal/mol	Ccb	Murrin and Goldhagen, 1957	ALS
Quantity	Value	Units	Method	Reference	Comment
Δ_cH°_liquid	-652.99 ± 0.45	kcal/mol	Ccb	Murrin and Goldhagen, 1957	Corresponding Δ_fHº_liquid = -64.79 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS
Quantity	Value	Units	Method	Reference	Comment
S°_liquid	60.59	cal/mol*K	N/A	Counsell, Lee, et al., 1971	DH
S°_liquid	60.40	cal/mol*K	N/A	Parks, Kelley, et al., 1929	Extrapolation below 90 K, 58.6 J/mol*K. Revision of previous data.; DH
S°_liquid	67.71	cal/mol*K	N/A	Parks and Huffman, 1926	Extrapolation below 90 K, 88.70 J/mol*K.; DH

Constant pressure heat capacity of liquid

C_p,liquid (cal/mol*K)	Temperature (K)	Reference	Comment
41.23	298.15	Counsell, Lee, et al., 1971	T = 15 to 300 K.; DH
41.080	293.15	Mazur, 1939	T = -112 to 20°C.; DH
41.11	293.	Mazur, 1939, 2	T = -110 to 20°C.; DH
40.01	290.	Kurnakov and Voskresenskaya, 1936	DH
39.39	255.2	Aoyama and Kanda, 1935	T = 80 to 255 K. Value is unsmoothed experimental datum.; DH
43.00	308.	Bennewitz and Wendroth, 1927	T = 308 to 488 K. Value is unsmoothed experimental datum. Pressure 40 atmospheres.; DH
40.80	290.0	Parks and Huffman, 1926	T = 76 to 290 K. Value is unsmoothed experimental datum.; DH
42.81	286.6	Keyes and Beattie, 1924	T = 274, 286 K.; DH

Gas phase ion energetics data

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, References, Notes

Data evaluated as indicated in comments:
HL - Edward P. Hunter and Sharon G. Lias
L - Sharon G. Lias

Data compiled as indicated in comments:
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

Quantity	Value	Units	Method	Reference	Comment
IE (evaluated)	9.51 ± 0.03	eV	N/A	N/A	L
Quantity	Value	Units	Method	Reference	Comment
Proton affinity (review)	198.0	kcal/mol	N/A	Hunter and Lias, 1998	HL
Quantity	Value	Units	Method	Reference	Comment
Gas basicity	191.	kcal/mol	N/A	Hunter and Lias, 1998	HL

Ionization energy determinations

IE (eV)	Method	Reference	Comment
9.52 ± 0.07	EI	Bowen and Maccoll, 1984	LBLHLM
9.60 ± 0.01	PI	Botter, Pechine, et al., 1977	LLK
9.41	PE	Behan, Dean, et al., 1976	LLK
9.50 ± 0.01	PE	Cocksey, Eland, et al., 1971	LLK
9.51	PE	Dewar and Worley, 1969	RDSH
9.53 ± 0.02	PI	Watanabe, 1957	RDSH
9.61	PE	Ohno, Imai, et al., 1985	Vertical value; LBLHLM
9.66	PE	Aue and Bowers, 1979	Vertical value; LLK
9.59	PE	Benoit and Harrison, 1977	Vertical value; LLK
9.701	PE	Aue, Webb, et al., 1975	Vertical value; LLK

Appearance energy determinations

Ion	AE (eV)	Other Products	Method	Reference	Comment
CH₃O⁺	12.28 ± 0.05	C₂H₄+CH₃	EI	Selim and Helal, 1981	LLK
CH₃O⁺	11.92	?	EI	Holmes, Rye, et al., 1979	LLK
CH₃O⁺	12.1	?	EI	Harrison, Ivko, et al., 1966	RDSH
C₂H₅⁺	12.0 ± 0.1	?	EI	Williams and Hamill, 1968	RDSH
C₂H₅O⁺	11.85	C₂H₅	EI	Lossing, 1977	LLK
C₂H₅O⁺	11.83	C₂H₅	EI	Phillips, Russell, et al., 1975	LLK
C₂H₅O⁺	11.8	C₂H₅	EI	Harrison, Ivko, et al., 1966	RDSH
C₃H₅⁺	11.6	?	EI	Tsang and Harrison, 1970	RDSH
C₃H₇O⁺	10.26 ± 0.08	CH₃	EI	Bowen and Maccoll, 1984	LBLHLM
C₃H₇O⁺	10.26	CH₃	EI	Lossing, 1977	LLK
C₃H₇O⁺	10.3	CH₃	EI	Harrison, Ivko, et al., 1966	RDSH

References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Gas phase ion energetics data, Notes

Pihlaja and Heikkil, 1968
Pihlaja, K.; Heikkil, J., Heats of combustion. Diethyl ether and 1,1-diethoxyethane, Acta Chem. Scand., 1968, 22, 2731-2732. [all data]

Pedley, Naylor, et al., 1986
Pedley, J.B.; Naylor, R.D.; Kirby, S.P., Thermochemical Data of Organic Compounds, Chapman and Hall, New York, 1986, 1-792. [all data]

Pilcher, Skinner, et al., 1963
Pilcher, G.; Skinner, H.A.; Pell, A.S.; Pope, A.E., Measurements of heats of combustion by flame calorimetry. Part 1.-Diethyl ether, ethyl vinyl ether and divinyl ether, Trans. Faraday Soc., 1963, 59, 316-330. [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]

Counsell J.F., 1971
Counsell J.F., Thermodynamic properties of organic oxygen compounds. Part XXVI. Diethyl ether, J. Chem. Soc. A, 1971, 313-316. [all data]

Cope C.S., 1959
Cope C.S., Equilibria in the hydration of ethylene at elevated pressures and temperatures, A. I. Ch. E. Journal, 1959, 5, 10-16. [all data]

Stull D.R., 1969
Stull D.R., Jr., The Chemical Thermodynamics of Organic Compounds. Wiley, New York, 1969. [all data]

Chao J., 1986
Chao J., Thermodynamic properties of key organic oxygen compounds in the carbon range C1 to C4. Part 2. Ideal gas properties, J. Phys. Chem. Ref. Data, 1986, 15, 1369-1436. [all data]

Jennings W.H., 1934
Jennings W.H., Specific heat of furan and ethyl ether vapors, J. Phys. Chem., 1934, 38, 747-751. [all data]

Jatkar S.K.K., 1939
Jatkar S.K.K., Supersonic velocity in gases and vapors. V. Heat capacity of vapors of acetone, benzene, cyclohexane, hexane and methyl, ethyl and propyl ethers, J. Indian Inst. Sci., 1939, A22, 19-37. [all data]

Valentin F.H.H., 1950
Valentin F.H.H., Equilibrium and thermodynamic relation in the vapor-phase catalytic dehydration of ethyl alcohol to ethyl ether, J. Chem. Soc., 1950, 498-500. [all data]

Counsell, Lee, et al., 1971
Counsell, J.F.; Lee, D.A.; Martin, J.F., Thermodynamic properties of organic oxygen compounds. Part XXVI. Diethyl ether, 1971, J. [all data]

Parks, Kelley, et al., 1929
Parks, G.S.; Kelley, K.K.; Huffman, H.M., Thermal data on organic compounds. V. A revision of the entropies and free energies of nineteen organic compounds, J. Am. Chem. Soc., 1929, 51, 1969-1973. [all data]

Parks and Huffman, 1926
Parks, G.S.; Huffman, H.M., Thermal data on organic compounds. IV. The heat capacities, entropies and free energies of normal propyl alcohol, ethyl ether and dulcitol, J. Am. Chem. Soc., 1926, 48, 2788-2793. [all data]

Mazur, 1939
Mazur, J., Über die spezifische Wärme des Äthyläthers, Acta Phys. Pol., 1939, 7, 318-326. [all data]

Mazur, 1939, 2
Mazur, J., Über die spezifische Wärme des Äthyläthers, des Nitrobenzols und des Schwefelkohlenstoffs, Z. Physik., 1939, 113, 710-720. [all data]

Kurnakov and Voskresenskaya, 1936
Kurnakov, N.S.; Voskresenskaya, N.K., Calorimetry of liquid binary systems, Izv. Akad. Nauk SSSR, Otdel. Mat. i Estestv. Nauk. Ser. Khim, 1936, 1936, 439-461. [all data]

Aoyama and Kanda, 1935
Aoyama, S.; Kanda, E., Studies on the heat capacities at low temperature. Report I. Heat capacities of some organic substances at low temperature, Sci. Rept. Tohoku Imp. Univ. [1]24, 1935, 107-115. [all data]

Bennewitz and Wendroth, 1927
Bennewitz, K.; Wendroth, H., Untersuchungen im kritischen Gebiet. II. Bestimmung der wahren spezifischen Wärme Cp des flüssigne Äthyläthers oberund unterhalb der kritischen Temperatur, Z. Phys. Chem., 1927, 125, 111-134. [all data]

Keyes and Beattie, 1924
Keyes, F.G.; Beattie, J.A., A calorimeter for measuring specific heats and heats of vaporization of liquids. The specific heat and heat of vaporization of liquid ethyl ether at 0° and 12°, J. Am. Chem. Soc., 1924, 46, 1753-1760. [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]

Bowen and Maccoll, 1984
Bowen, R.D.; Maccoll, A., Low energy, low temperature mass spectra, Org. Mass Spectrom., 1984, 19, 379. [all data]

Botter, Pechine, et al., 1977
Botter, R.; Pechine, J.M.; Rosenstock, H.M., Photoionization of dimethyl ether and diethyl ether, Int. J. Mass Spectrom. Ion Phys., 1977, 25, 7. [all data]

Behan, Dean, et al., 1976
Behan, J.M.; Dean, F.M.; Johnstone, R.A.W., Photoelectron spectra of cyclic aromatic ethers. The question of the Mills-Nixon effect, Tetrahedron, 1976, 32, 167. [all data]

Cocksey, Eland, et al., 1971
Cocksey, B.J.; Eland, J.H.D.; Danby, C.J., The effect of alkyl substitution on ionisation potential, J. Chem. Soc., 1971, (B), 790. [all data]

Dewar and Worley, 1969
Dewar, M.J.S.; Worley, S.D., Photoelectron spectra of molecules. I. Ionization potentials of some organic molecules and their interpretation, J. Chem. Phys., 1969, 50, 654. [all data]

Watanabe, 1957
Watanabe, K., Ionization potentials of some molecules, J. Chem. Phys., 1957, 26, 542. [all data]

Ohno, Imai, et al., 1985
Ohno, K.; Imai, K.; Harada, Y., Variations in reactivity of lone-pair electrons due to intramolecular hydrogen bonding as observed by penning ionization electron spectroscopy, J. Am. Chem. Soc., 1985, 107, 8078. [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]

Aue, Webb, et al., 1975
Aue, D.H.; Webb, H.M.; Bowers, M.T., Proton affinities, ionization potentials, and hydrogen affinities of nitrogen and oxygen bases. Hybridization effects, J. Am. Chem. Soc., 1975, 97, 4137. [all data]

Selim and Helal, 1981
Selim, E.T.M.; Helal, A.I., Heat of formation of CH₂=OH⁺ fragment ion, Indian J. Pure Appl. Phys., 1981, 19, 977. [all data]

Holmes, Rye, et al., 1979
Holmes, J.L.; Rye, R.T.B.; Terlouw, J.K., On the loss of ethylene from [C₃H₇O]⁺ ions of structure CH₃CH₂CHOH, Org. Mass Spectrom., 1979, 14, 606. [all data]

Harrison, Ivko, et al., 1966
Harrison, A.G.; Ivko, A.; Van Raalte, D., Energetics of formation of some oxygenated ions and the proton affinities of carbonyl compounds, Can. J. Chem., 1966, 44, 1625. [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]

Lossing, 1977
Lossing, F.P., Heats of formation of some isomeric [C_nH_2n+1]⁺ ions. Substitutional effects on ion stability, J. Am. Chem. Soc., 1977, 99, 7526. [all data]

Phillips, Russell, et al., 1975
Phillips, G.R.; Russell, M.E.; Solka, B.H., The structure of the [C₂H₅O]⁺ ion in the mass spectrum of diethyl ether, Org. Mass Spectrom., 1975, 10, 819. [all data]

Tsang and Harrison, 1970
Tsang, C.W.; Harrison, A.G., Four-centred rearrangements in the mass spectra of aliphatic ethers, Org. Mass Spectrom., 1970, 3, 647. [all data]

Notes

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Gas phase ion energetics data, References

Symbols used in this document:

AE	Appearance energy
C_p,gas	Constant pressure heat capacity of gas
C_p,liquid	Constant pressure heat capacity of liquid
IE (evaluated)	Recommended ionization energy
S°_gas	Entropy of gas at standard conditions
S°_liquid	Entropy of liquid at standard conditions
Δ_cH°_gas	Enthalpy of combustion of gas at standard conditions
Δ_cH°_liquid	Enthalpy of combustion of liquid at standard conditions
Δ_fH°_gas	Enthalpy of formation of gas at standard conditions
Δ_fH°_liquid	Enthalpy of formation of liquid at standard conditions

Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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