Ethyl ether

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Gas 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 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
Δfgas-60.40 ± 0.47kcal/molCcbPihlaja and Heikkil, 1968Reanalyzed by Pedley, Naylor, et al., 1986, Original value = -59.82 ± 0.44 kcal/mol; ALS
Δfgas-60.28 ± 0.19kcal/molCmPilcher, Skinner, et al., 1963ALS
Δfgas-58.4kcal/molCcbMurrin and Goldhagen, 1957ALS
Quantity Value Units Method Reference Comment
Δcgas-651.60 ± 0.43kcal/molCcbPihlaja and Heikkil, 1968Corresponding Δfgas = -66.18 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS
Δcgas-657.52 ± 0.18kcal/molCmPilcher, Skinner, et al., 1963Corresponding Δfgas = -60.26 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS
Quantity Value Units Method Reference Comment
gas81.79cal/mol*KN/ACounsell J.F., 1971Other 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

Cp,gas (cal/mol*K) Temperature (K) Reference Comment
14.94100.Chao J., 1986p=1 bar.; GT
20.27150.
23.83200.
27.318273.15
28.552 ± 0.036298.15
28.647300.
34.132400.
39.620500.
44.539600.
48.841700.
52.591800.
55.865900.
58.7191000.
61.2051100.
63.3651200.
65.2411300.
66.8761400.
68.2981500.

Constant pressure heat capacity of gas

Cp,gas (cal/mol*K) Temperature (K) Reference Comment
29.144309.98Counsell J.F., 1971Other 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
30.251329.99
31.386350.00
32.794375.00
34.242400.01
35.636424.99
37.072450.04

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 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
Δfliquid-64.81 ± 0.45kcal/molCcbMurrin and Goldhagen, 1957ALS
Quantity Value Units Method Reference Comment
Δcliquid-652.99 ± 0.45kcal/molCcbMurrin and Goldhagen, 1957Corresponding Δfliquid = -64.79 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS
Quantity Value Units Method Reference Comment
liquid60.59cal/mol*KN/ACounsell, Lee, et al., 1971DH
liquid60.40cal/mol*KN/AParks, Kelley, et al., 1929Extrapolation below 90 K, 58.6 J/mol*K. Revision of previous data.; DH
liquid67.71cal/mol*KN/AParks and Huffman, 1926Extrapolation below 90 K, 88.70 J/mol*K.; DH

Constant pressure heat capacity of liquid

Cp,liquid (cal/mol*K) Temperature (K) Reference Comment
41.23298.15Counsell, Lee, et al., 1971T = 15 to 300 K.; DH
41.080293.15Mazur, 1939T = -112 to 20°C.; DH
41.11293.Mazur, 1939, 2T = -110 to 20°C.; DH
40.01290.Kurnakov and Voskresenskaya, 1936DH
39.39255.2Aoyama and Kanda, 1935T = 80 to 255 K. Value is unsmoothed experimental datum.; DH
43.00308.Bennewitz and Wendroth, 1927T = 308 to 488 K. Value is unsmoothed experimental datum. Pressure 40 atmospheres.; DH
40.80290.0Parks and Huffman, 1926T = 76 to 290 K. Value is unsmoothed experimental datum.; DH
42.81286.6Keyes and Beattie, 1924T = 274, 286 K.; DH

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
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 ± 0.03eVN/AN/AL
Quantity Value Units Method Reference Comment
Proton affinity (review)198.0kcal/molN/AHunter and Lias, 1998HL
Quantity Value Units Method Reference Comment
Gas basicity191.kcal/molN/AHunter and Lias, 1998HL

Ionization energy determinations

IE (eV) Method Reference Comment
9.52 ± 0.07EIBowen and Maccoll, 1984LBLHLM
9.60 ± 0.01PIBotter, Pechine, et al., 1977LLK
9.41PEBehan, Dean, et al., 1976LLK
9.50 ± 0.01PECocksey, Eland, et al., 1971LLK
9.51PEDewar and Worley, 1969RDSH
9.53 ± 0.02PIWatanabe, 1957RDSH
9.61PEOhno, Imai, et al., 1985Vertical value; LBLHLM
9.66PEAue and Bowers, 1979Vertical value; LLK
9.59PEBenoit and Harrison, 1977Vertical value; LLK
9.701PEAue, Webb, et al., 1975Vertical value; LLK

Appearance energy determinations

Ion AE (eV) Other Products MethodReferenceComment
CH3O+12.28 ± 0.05C2H4+CH3EISelim and Helal, 1981LLK
CH3O+11.92?EIHolmes, Rye, et al., 1979LLK
CH3O+12.1?EIHarrison, Ivko, et al., 1966RDSH
C2H5+12.0 ± 0.1?EIWilliams and Hamill, 1968RDSH
C2H5O+11.85C2H5EILossing, 1977LLK
C2H5O+11.83C2H5EIPhillips, Russell, et al., 1975LLK
C2H5O+11.8C2H5EIHarrison, Ivko, et al., 1966RDSH
C3H5+11.6?EITsang and Harrison, 1970RDSH
C3H7O+10.26 ± 0.08CH3EIBowen and Maccoll, 1984LBLHLM
C3H7O+10.26CH3EILossing, 1977LLK
C3H7O+10.3CH3EIHarrison, Ivko, et al., 1966RDSH

References

Go To: Top, Gas phase thermochemistry data, Condensed phase 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.

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 [CnH2n+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

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