Methyl formate

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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:
DRB - Donald R. Burgess, Jr.
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-80.52kcal/molN/AGladii, Starchevskii, et al., 1990Value computed using ΔfHliquid° value of -365.9 kj/mol from Gladii, Starchevskii, et al., 1990 and ΔvapH° value of 29.0 kj/mol from Hine and Klueppet, 1974.; DRB
Δfgas-83.41kcal/molN/AGuthrie, 1974Value computed using ΔfHliquid° value of -378.0 kj/mol from Guthrie, 1974 and ΔvapH° value of 29.0 kj/mol from Hine and Klueppet, 1974.; DRB
Δfgas-86.6kcal/molCmHine and Klueppet, 1974ALS
Δfgas-84.97kcal/molCcrHall and Baldt, 1971ALS

Constant pressure heat capacity of gas

Cp,gas (cal/mol*K) Temperature (K) Reference Comment
10.53100.Chao J., 1986p=1 bar. Recommended S(T) and Cp(T) values are in close agreement with statistical values calculated by [ Vay P.-M., 1971] (discrepancies in S(T) do not exceed 1.3 J/mol*K) and value of S(298.15 K)=286.10 J/mol*K determined from high accuracy ab initio calculation [ East A.L.L., 1997].; GT
11.91150.
12.95200.
14.69273.15
15.39 ± 0.02298.15
15.44300.
18.54400.
21.58500.
24.276600.
26.592700.
28.568800.
30.261900.
31.7111000.
32.9571100.
34.0301200.
34.9521300.
35.7501400.
36.4441500.

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-87.45kcal/molEqkGladii, Starchevskii, et al., 1990ALS
Δfliquid-90.35kcal/molCmGuthrie, 1974Heat of hydrolysis; ALS
Δfliquid-93.4kcal/molCmHine and Klueppet, 1974ALS
Δfliquid-92.28kcal/molCcrHall and Baldt, 1971ALS
Quantity Value Units Method Reference Comment
Δcliquid-232.46 ± 0.14kcal/molCcrHall and Baldt, 1971Corresponding Δfliquid = -92.27 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
28.817298.75Zabransky, Hynek, et al., 1987T = 293 to 299 K. Unsmoothed experimental datum.; DH
28.61298.15Fuchs, 1979DH
22.8297.Hall and Baldt, 1971DH
28.99288.Mehl, 1934DH
31.1298.Berthelot and Ogier, 1881T = 286 to 302 K. Cp given as 0.516 cal/g*K.; DH

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
Tboil305. ± 1.KAVGN/AAverage of 20 values; Individual data points
Quantity Value Units Method Reference Comment
Tfus173.2KN/ATimmermans, 1935Uncertainty assigned by TRC = 2. K; TRC
Tfus173.4KN/ATimmermans, 1911Uncertainty assigned by TRC = 0.3 K; TRC
Quantity Value Units Method Reference Comment
Tc487.2KN/AMajer and Svoboda, 1985 
Tc487.2KN/AYoung, 1910Uncertainty assigned by TRC = 1. K; TRC
Tc487.2KN/AYoung and Thomas, 1893Uncertainty assigned by TRC = 1. K; TRC
Tc523.7KN/ADe Heen, 1888Uncertainty assigned by TRC = 20. K; TRC
Tc485.2KN/ANadezhdin, 1887Uncertainty assigned by TRC = 2. K; TRC
Quantity Value Units Method Reference Comment
Pc59.25atmN/AYoung, 1910Uncertainty assigned by TRC = 0.6000 atm; TRC
Pc59.289atmN/AYoung and Thomas, 1893Uncertainty assigned by TRC = 0.39 atm; TRC
Pc61.65atmN/ANadezhdin, 1887Uncertainty assigned by TRC = 2.0000 atm; TRC
Quantity Value Units Method Reference Comment
ρc5.818mol/lN/AYoung, 1910Uncertainty assigned by TRC = 0.08 mol/l; TRC
ρc5.818mol/lN/AYoung and Thomas, 1893Uncertainty assigned by TRC = 0.07 mol/l; TRC
Quantity Value Units Method Reference Comment
Δvap7.0 ± 0.5kcal/molAVGN/AAverage of 6 values; Individual data points

Enthalpy of vaporization

ΔvapH (kcal/mol) Temperature (K) Method Reference Comment
6.673304.7N/AMajer and Svoboda, 1985 
7.07292.AStephenson and Malanowski, 1987Based on data from 279. to 305. K.; AC
6.79320.AStephenson and Malanowski, 1987Based on data from 305. to 443. K.; AC
6.86 ± 0.02293.CCihlár, Hynek, et al., 1976AC
6.67 ± 0.02305.CCihlár, Hynek, et al., 1976AC
6.55 ± 0.02313.CCihlár, Hynek, et al., 1976AC
7.19283.BGBaldt and Hall, 1971Based on data from 261. to 305. K.; AC

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
293. to 314.11.020.3119487.2Majer and Svoboda, 1985 

Antoine Equation Parameters

log10(P) = A − (B / (T + C))
    P = vapor pressure (atm)
    T = temperature (K)

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Temperature (K) A B C Reference Comment
294. to 304.90.245266.524-278.54Nelson, 1928Coefficents calculated by NIST from author's data.

In addition to the Thermodynamics Research Center (TRC) data available from this site, much more physical and chemical property data is available from the following TRC products:


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:
B - John E. Bartmess
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

C2H3O2- + Hydrogen cation = Methyl formate

By formula: C2H3O2- + H+ = C2H4O2

Quantity Value Units Method Reference Comment
Δr<384.00kcal/molCIDTGraul and Squires, 1988gas phase; B
Δr<391.75 ± 0.90kcal/molG+TSDePuy, Grabowski, et al., 1985gas phase; HO- + DCO2CH3 -> (M-D)-. ΔHf(MeO- + CO) = -59.7 kcal/mol; B
Quantity Value Units Method Reference Comment
Δr<384.00kcal/molIMRBDePuy, Grabowski, et al., 1985gas phase; HO- + DCO2CH3 -> (M-D)-. ΔHf(MeO- + CO) = -59.7 kcal/mol; B

C2H3O2- + Hydrogen cation = Methyl formate

By formula: C2H3O2- + H+ = C2H4O2

Quantity Value Units Method Reference Comment
Δr391.2 ± 4.1kcal/molG+TSDePuy, Grabowski, et al., 1985gas phase; B
Quantity Value Units Method Reference Comment
Δr384.1 ± 4.0kcal/molIMRBDePuy, Grabowski, et al., 1985gas phase; B

Methane, trimethoxy- + Water = Methyl formate + 2Methyl Alcohol

By formula: C4H10O3 + H2O = C2H4O2 + 2CH4O

Quantity Value Units Method Reference Comment
Δr-2.29 ± 0.28kcal/molCmHine and Klueppet, 1974liquid phase; ALS

Henry's Law 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: Rolf Sander

Henry's Law constant (water solution)

kH(T) = H exp(d(ln(kH))/d(1/T) ((1/T) - 1/(298.15 K)))
H = Henry's law constant for solubility in water at 298.15 K (mol/(kg*bar))
d(ln(kH))/d(1/T) = Temperature dependence constant (K)

H (mol/(kg*bar)) d(ln(kH))/d(1/T) (K) Method Reference Comment
4.1 MN/A 
4.5 QN/A missing citation is quoted as the source. However, there only activity coefficients and no vapor pressures are listed.
4.5 QN/A missing citation is quoted as the source. However, there only activity coefficients and no vapor pressures are listed.
4.13800.MN/A 

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:
B - John E. Bartmess
LL - Sharon G. Lias and Joel F. Liebman
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

View reactions leading to C2H4O2+ (ion structure unspecified)

Quantity Value Units Method Reference Comment
IE (evaluated)10.835eVN/AN/AL
Quantity Value Units Method Reference Comment
Proton affinity (review)187.0kcal/molN/AHunter and Lias, 1998HL
Quantity Value Units Method Reference Comment
Gas basicity179.6kcal/molN/AHunter and Lias, 1998HL

Ionization energy determinations

IE (eV) Method Reference Comment
10.835TEWaterstradt, Jung, et al., 1994LL
~10.7PECannington and Ham, 1985LBLHLM
10.99PEKimura, Katsumata, et al., 1981LLK
10.85 ± 0.05PEBenoit, Harrison, et al., 1977LLK
10.85PESweigart and Turner, 1972LLK
10.815 ± 0.005PIWatanabe, Nakayama, et al., 1962RDSH
11.0PECannington and Ham, 1985Vertical value; LBLHLM
10.85PEBenoit and Harrison, 1977Vertical value; LLK
10.3PERao, 1975Vertical value; LLK

Appearance energy determinations

Ion AE (eV) Other Products MethodReferenceComment
CHO+12.91 ± 0.07CH3OPIPECONishimura, Zha, et al., 1987LBLHLM
CHO+13.47 ± 0.05CH3OEIHaney and Franklin, 1969RDSH
CHO2+15.9CH3EIKing and Long, 1958RDSH
CH2+19.8?EIKing and Long, 1958RDSH
CH2O+13.6?EIKing and Long, 1958RDSH
CH3+13.27 ± 0.24HCO2PIPECONishimura, Zha, et al., 1987LBLHLM
CH3+13.71?EIHaney and Franklin, 1969RDSH
CH3O+12.23CHOEIHaney and Franklin, 1969RDSH
CH4O+11.47 ± 0.05COPIPECONishimura, Zha, et al., 1987LBLHLM
CH4O+11.5 ± 0.1COEIVanRaalte and Harrison, 1963RDSH
C2H3O2+12.3HEIKing and Long, 1958RDSH

De-protonation reactions

C2H3O2- + Hydrogen cation = Methyl formate

By formula: C2H3O2- + H+ = C2H4O2

Quantity Value Units Method Reference Comment
Δr<384.00kcal/molCIDTGraul and Squires, 1988gas phase; B
Δr<391.75 ± 0.90kcal/molG+TSDePuy, Grabowski, et al., 1985gas phase; HO- + DCO2CH3 -> (M-D)-. ΔHf(MeO- + CO) = -59.7 kcal/mol; B
Quantity Value Units Method Reference Comment
Δr<384.00kcal/molIMRBDePuy, Grabowski, et al., 1985gas phase; HO- + DCO2CH3 -> (M-D)-. ΔHf(MeO- + CO) = -59.7 kcal/mol; B

C2H3O2- + Hydrogen cation = Methyl formate

By formula: C2H3O2- + H+ = C2H4O2

Quantity Value Units Method Reference Comment
Δr391.2 ± 4.1kcal/molG+TSDePuy, Grabowski, et al., 1985gas phase; B
Quantity Value Units Method Reference Comment
Δr384.1 ± 4.0kcal/molIMRBDePuy, Grabowski, et al., 1985gas phase; B

IR Spectrum

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Henry's Law data, Gas phase ion energetics data, Mass spectrum (electron ionization), References, Notes

Data compiled by: Coblentz Society, Inc.

Data compiled by: Tanya L. Myers, Russell G. Tonkyn, Ashley M. Oeck, Tyler O. Danby, John S. Loring, Matthew S. Taubman, Stephen W. Sharpe, Jerome C. Birnbaum, and Timothy J. Johnson

Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director


Mass spectrum (electron ionization)

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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: NIST Mass Spectrometry Data Center, William E. Wallace, director

Spectrum

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Additional Data

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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-3741
NIST MS number 228212

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References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Henry's Law data, Gas phase ion energetics 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.

Gladii, Starchevskii, et al., 1990
Gladii, S.L.; Starchevskii, M.K.; Pazderskii, Yu.A.; Moiseev, I.I., Chemical equilibrium in the methyl formate-water-methanol-formic acid system, J. Appl. Chem. USSR, 1990, 63, 106-111. [all data]

Hine and Klueppet, 1974
Hine, J.; Klueppet, A.W., Structural effects on rates and equilibria. XVIII. Thermodynamic stability of ortho esters, J. Am. Chem. Soc., 1974, 96, 2924-2929. [all data]

Guthrie, 1974
Guthrie, J.P., Hydration of carboxamides. Evaluation of the free energy change for addition of water to acetamide and formamide derivatives, J. Am. Chem. Soc., 1974, 96, 3608-3615. [all data]

Hall and Baldt, 1971
Hall, H.K., Jr.; Baldt, J.H., Thermochemistry of strained-ring bridgehead nitriles and esters, J. Am. Chem. Soc., 1971, 93, 140-145. [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]

Vay P.-M., 1971
Vay P.-M., Tables of thermodynamic functions for gaseous methyl formate and methyl acetate, J. Chim. Phys. Physico-Chim. Biol., 1971, 68, 1757-1758. [all data]

East A.L.L., 1997
East A.L.L., Ab initio statistical thermodynamical models for the computation of third-law entropies, J. Chem. Phys., 1997, 106, 6655-6674. [all data]

Zabransky, Hynek, et al., 1987
Zabransky, M.; Hynek, V.; Finkeova-Hastabova, J.; Vesely, F., Heat capacities of six liquid esters as a function of temperature, Coll. Czech. Chem. Comm., 1987, 52, 251-256. [all data]

Fuchs, 1979
Fuchs, R., Heat capacities of some liquid aliphatic, alicyclic, and aromatic esters at 298.15 K, J. Chem. Thermodyn., 1979, 11, 959-961. [all data]

Mehl, 1934
Mehl, W., Die spezifische Wärme einiger flüssiger Kältemittel, Z. ges. Kalte-Ind., 1934, 41, 152-153. [all data]

Berthelot and Ogier, 1881
Berthelot, M.; Ogier, J., Recherches sur les ethers formiques, Ann. chim. et phys., 1881, 23(5), 201-209. [all data]

Timmermans, 1935
Timmermans, J., Researches in Stoichiometry. I. The Heat of Fusion of Organic Compounds., Bull. Soc. Chim. Belg., 1935, 44, 17-40. [all data]

Timmermans, 1911
Timmermans, J., Researches on the freezing point of organic liquid compounds, Bull. Soc. Chim. Belg., 1911, 25, 300. [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]

Young, 1910
Young, S., The Internal Heat of Vaporization constants of thirty pure substances, Sci. Proc. R. Dublin Soc., 1910, 12, 374. [all data]

Young and Thomas, 1893
Young, S.; Thomas, G.L., The vapour pressures, molecular volumes, and critical constants of ten of the lower esters, J. Chem. Soc., 1893, 63, 1191. [all data]

De Heen, 1888
De Heen, P., Research on Physics and Theory of Liquids, Experimental Part Paris, 1888. [all data]

Nadezhdin, 1887
Nadezhdin, A., Rep. Phys., 1887, 23, 708. [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]

Cihlár, Hynek, et al., 1976
Cihlár, J.; Hynek, V.; Svoboda, V.; Holub, R., Heats of vaporization of alkyl esters of formic acid, Collect. Czech. Chem. Commun., 1976, 41, 1, 1-6, https://doi.org/10.1135/cccc19760001 . [all data]

Baldt and Hall, 1971
Baldt, J.H.; Hall, H.K.K., Jr., Thermochemistry of strained-ring bridgehead nitriles and esters, J. Am. Chem. Soc., 1971, 93, 140-145. [all data]

Nelson, 1928
Nelson, O.A., Vapor Pressures of Fumigants: II---Methyl, Ethyl, n-Propyl, Isopropyl, n-Butyl, Secondary Butyl and Isobutyl Formates 1, Ind. Eng. Chem., 1928, 20, 12, 1382-1384, https://doi.org/10.1021/ie50228a035 . [all data]

Graul and Squires, 1988
Graul, S.T.; Squires, R.R., On the Existence of Alkyl Carbanions in the Gas Phase, J. Am. Chem. Soc., 1988, 110, 2, 607, https://doi.org/10.1021/ja00210a054 . [all data]

DePuy, Grabowski, et al., 1985
DePuy, C.H.; Grabowski, J.J.; Bierbaum, V.M.; Ingemann, S.; Nibbering, N.M.M., Gas-phase reactions of anions with methyl formate and N,N-dimethylformamide, J. Am. Chem. Soc., 1985, 107, 1093. [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]

Waterstradt, Jung, et al., 1994
Waterstradt, E.; Jung, R.; Belling, T.; Muller-Dethlefs, K., Zero kinetic energy (ZEKE) photoelectron spectrum and coincident mass spectra of methyl formate, Ber. Bunsen-Ges. Phys. Chem., 1994, 98, 176. [all data]

Cannington and Ham, 1985
Cannington, P.H.; Ham, N.S., He(II) photoelectron spectra of esters, J. Electron Spectrosc. Relat. Phenom., 1985, 36, 203. [all data]

Kimura, Katsumata, et al., 1981
Kimura, K.; Katsumata, S.; Achiba, Y.; Yamazaki, T.; Iwata, S., Ionization energies, Ab initio assignments, and valence electronic structure for 200 molecules in Handbook of HeI Photoelectron Spectra of Fundamental Organic Compounds, Japan Scientific Soc. Press, Tokyo, 1981. [all data]

Benoit, Harrison, et al., 1977
Benoit, F.M.; Harrison, A.G.; Lossing, F.P., Hydrogen migrations in mass spectrometry III-Energetics of formation of [R'CO2H2]+ in the mass spectra of R'CO2R, Org. Mass Spectrom., 1977, 12, 78. [all data]

Sweigart and Turner, 1972
Sweigart, D.A.; Turner, D.W., Lone pair orbitals and their interactions studied by photoelectron spectroscopy. I. Carboxylic acids and their derivatives, J. Am. Chem. Soc., 1972, 94, 5592. [all data]

Watanabe, Nakayama, et al., 1962
Watanabe, K.; Nakayama, T.; Mottl, J., Ionization potentials of some molecules, J. Quant. Spectry. Radiative Transfer, 1962, 2, 369. [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]

Rao, 1975
Rao, C.N.R., Lone-pair ionization bands of chromophores in the photoelectron spectra of organic molecules, Indian J. Chem., 1975, 13, 950. [all data]

Nishimura, Zha, et al., 1987
Nishimura, T.; Zha, Q.; Meisels, G.G., Unimolecular dissociation of energy-selected methyl formate ion, J. Chem. Phys., 1987, 87, 4589. [all data]

Haney and Franklin, 1969
Haney, M.A.; Franklin, J.L., Excess energies in mass spectra of some oxygen-containing organic compounds, J. Chem. Soc. Faraday Trans., 1969, 65, 1794. [all data]

King and Long, 1958
King, A.B.; Long, F.A., Mass spectra of some simple esters and their interpretation by quasi-equilibrium theory, J. Chem. Phys., 1958, 29, 374. [all data]

VanRaalte and Harrison, 1963
VanRaalte, D.; Harrison, A.G., Ionization and dissociation of formate esters by electron impact, Can. J. Chem., 1963, 41, 2054. [all data]


Notes

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Henry's Law data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), References