Methane, nitro-

• Formula: CH₃NO₂
• Molecular weight: 61.0400
• IUPAC Standard InChI: InChI=1S/CH3NO2/c1-2(3)4/h1H3 Copy

  
• IUPAC Standard InChIKey: LYGJENNIWJXYER-UHFFFAOYSA-N Copy
• CAS Registry Number: 75-52-5
• 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: Nitromethane; Nitrocarbol; CH3NO2; Nitrometan; UN 1261; NM; NSC 428
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• Information on this page:
  • Gas phase thermochemistry data
  • Condensed phase thermochemistry data
  • Phase change data
  • Henry's Law data
  • Gas phase ion energetics data
  • References
  • Notes
• Other data available:
  • Reaction thermochemistry data
  • Ion clustering data
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • UV/Visible spectrum
  • Gas Chromatography
• Data at other public NIST sites:
  • Gas Phase Kinetics Database
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Gas phase thermochemistry data

Go To: Top, Condensed phase thermochemistry data, Phase change data, Henry's Law 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: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

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

Constant pressure heat capacity of liquid

Phase change data

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Henry's Law 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:
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
AC - William E. Acree, Jr., James S. Chickos
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DH - Eugene S. Domalski and Elizabeth D. Hearing

Enthalpy of vaporization

Enthalpy of vaporization

Δ_vapH = A exp(-βT_r) (1 − T_r)^β
    Δ_vapH = Enthalpy of vaporization (at saturation pressure) (kcal/mol)
    T_r = reduced temperature (T / T_c)

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Entropy of vaporization

Antoine Equation Parameters

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

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Enthalpy of fusion

Entropy of fusion

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)

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

Gas phase ion energetics data

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

Electron affinity determinations

Ionization energy determinations

Appearance energy determinations

De-protonation reactions

CH₂NO₂^- +  =

By formula: CH₂NO₂^- + H⁺ = CH₃NO₂

References

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

Knobel, Miroshnichenko, et al., 1971
Knobel, Y.K.; Miroshnichenko, E.A.; Lebedev, Y.A., Heats of combustion of nitromethane and dinitromethane: enthalpies of formation of nitromethyl radicals and energies of dissociation of bonds in nitro derivatives of methane, Bull. Acad. Sci. USSR, Div. Chem. Sci., 1971, 425-428. [all data]

Lebedeva and Ryadenko, 1973
Lebedeva, N.D.; Ryadenko, V.L.R., Enthalpies of formation of nitroalkanes, Russ. J. Phys. Chem. (Engl. Transl.), 1973, 47, 1382. [all data]

Cass, Fletcher, et al., 1958
Cass, R.C.; Fletcher, S.E.; Mortimer, C.T.; Quincey, P.G.; Springall, H.D., Heats of combustion and molecular structure. Part IV. Aliphatic nitroalkanes and nitric esters, J. Chem. Soc., 1958, 958-962. [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]

Holcomb and Dorsey, 1949
Holcomb, D.E.; Dorsey, C.L., Jr., Thermodynamic properties of nitroparaffins, Ind. Eng. Chem., 1949, 41, 2788-2792. [all data]

Swientoslawski, 1910
Swientoslawski, W., Thermochemische Untersuchungen der organischen Verbindungen. Dritte Mitteilung. Stickstoffhaltige Verbindungen., Z. Phys. Chem., 1910, 72, 49-83. [all data]

Jones and Giauque, 1947
Jones, W.M.; Giauque, W.F., The entropy of nitromethane. Heat capacity of solid and liquid. Vapor pressure, heats of fusion and vaporization, J. Am. Chem. Soc., 1947, 69, 983-987. [all data]

Berman and West, 1969
Berman, H.A.; West, E.D., Heat capacity of liquid nitromethane from 35 to 200°C, J. Chem. Eng. Data, 1969, 14, 107-109. [all data]

Hough, Mason, et al., 1950
Hough, E.W.; Mason, D.M.; Sage, B.H., Heat capacities of several organic liquids, J. Am. Chem. Soc., 1950, 72, 5775-5777. [all data]

Williams, 1925
Williams, J.W., A study of the physical properties of nitromethane, J. Am. Chem. Soc., 1925, 47, 2644-2652. [all data]

Toops, 1956
Toops, E.E., Physical Properties of High Purity Nitroparaffins, J. Phys. Chem., 1956, 60, 304-6. [all data]

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Jones and Giauque, 1947, 2
Jones, W.M.; Giauque, W.F., The Entropy of Nitromethane. Heat Capacity of Solid and Liquid. Vapor Pressure, Heats of Fusion and Vaporizaion, J. Am. Chem. Soc., 1947, 69, 983-7. [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]

Griffin, 1949
Griffin, D.N., The Critical Point of Nitromethane., J. Am. Chem. Soc., 1949, 71, 1423. [all data]

Ambrose, Counsell, et al., 1978
Ambrose, D.; Counsell, J.F.; Hicks, C.P., The correlation and estimation of vapour pressures: II a new procedure for estimation and extrapolation, J. Chem. Thermodyn., 1978, 10, 771. [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]

Berman and West, 1967
Berman, Horace A.; West, Estal Dale, Density and vapor pressure of nitromethane 26.degree. to 200.degree., J. Chem. Eng. Data, 1967, 12, 2, 197-199, https://doi.org/10.1021/je60033a011 . [all data]

McCullough, Scott, et al., 1954
McCullough, J.P.; Scott, D.W.; Pennington, R.E.; Hossenlopp, I.A.; Waddington, Guy, Nitromethane: The Vapor Heat Capacity, Heat of Vaporization, Vapor Pressure and Gas Imperfection; the Chemical Thermodynamic Properties from 0 to 1500°K., J. Am. Chem. Soc., 1954, 76, 19, 4791-4796, https://doi.org/10.1021/ja01648a008 . [all data]

Domalski and Hearing, 1996
Domalski, Eugene S.; Hearing, Elizabeth D., Heat Capacities and Entropies of Organic Compounds in the Condensed Phase. Volume III, J. Phys. Chem. Ref. Data, 1996, 25, 1, 1, https://doi.org/10.1063/1.555985 . [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]

Adams, Schneider, et al., 2009
Adams, C.L.; Schneider, H.; Ervin, K.M.; Weber, J.M., Low-energy photoelectron imaging spectroscopy of nitromethane anions: Electron affinity, vibrational features, anisotropies, and the dipole-bound state, J. Chem. Phys., 2009, 130, 7, 074307, https://doi.org/10.1063/1.3076892 . [all data]

Compton, Carman Jr., et al., 1996
Compton, R.N.; Carman Jr.; Desfrancois, C.; Abdoul-Carmine, H.; Schermann, J.P.; Hendricks, J.H., On the binding of Electrons to Nitromethane: Dipole and Valence Bound Anions, J. Chem. Phys., 1996, 105, 9, 3472, https://doi.org/10.1063/1.472993 . [all data]

Lecomte, Carles, et al., 2000
Lecomte, F.; Carles, S.; Desfrancois, C.; Johnson, M.A., Dipole bound and valence state coupling in argon-solvated nitromethane anions, J. Chem. Phys., 2000, 113, 24, 10973-10977, https://doi.org/10.1063/1.1326476 . [all data]

Chen, Welk, et al., 1999
Chen, E.C.M.; Welk, N.; Chen, E.S.; Wentworth, W.E., Electron affinity, gas-phase acidity, bond dissociation energy, and negative ion states of nitromethane, J. Phys. Chem. A, 1999, 103, 45, 9072-9079, https://doi.org/10.1021/jp990530l . [all data]

Chen and Wentworth, 1983
Chen, E.C.M.; Wentworth, W.E., Determination of molecular electron affinities using the electron capture detector in the pulse sampling mode at steady state, J. Phys. Chem., 1983, 87, 45. [all data]

Grimsrud, Caldwell, et al., 1985
Grimsrud, E.; Caldwell, G.; Kebarle, P., Electron affinities from electron transfer equilibria: A- + B = A + B-, J. Am. Chem. Soc., 1985, 107, 4627. [all data]

Compton, Reinhardt, et al., 1978
Compton, R.N.; Reinhardt, P.W.; Cooper, C.D., Collisional ionization between alkali atoms and some methane derivatives: Electron affinities for CH₃NO₂, CF₃I, and CF₃Br, J. Chem. Phys., 1978, 68, 4360. [all data]

Goebbert, Pichugin, et al., 2009
Goebbert, D.J.; Pichugin, K.; Sanov, A., Low-lying electronic states of CH3NO2 via photoelectron imaging of the nitromethane anion, J. Chem. Phys., 2009, 131, 16, 164308, https://doi.org/10.1063/1.3256233 . [all data]

Pasa-Tolic, Klasine, et al., 1990
Pasa-Tolic, L.; Klasine, L.; McGlynn, S.P., The HeI PE spectrum and electronic structure of nitroethene, Chem. Phys. Lett., 1990, 170, 113. [all data]

Lifshitz, Rejwan, et al., 1988
Lifshitz, C.; Rejwan, M.; Levin, I.; Peres, T., Unimolecular fragmentations of the nitromenthane cation, Int. J. Mass Spectrom. Ion Processes, 1988, 84, 271. [all data]

Ogden, Shaw, et al., 1983
Ogden, I.K.; Shaw, N.; Danby, C.J.; Powis, I., Competing dissociation channels of nitromethane and methyl nitrite ions and the role of electronic and internal modes of excitation, Int. J. Mass Spectrom. Ion Processes, 1983, 54, 41. [all data]

Gilman, Hsieh, et al., 1983
Gilman, J.P.; Hsieh, T.; Meisels, G.G., Competition between isomerization and fragmentation of gaseous ions. II. Nitromethane and methylnitrite ions, J. Chem. Phys., 1983, 78, 1174. [all data]

Katsumata, Shiromaru, et al., 1982
Katsumata, S.; Shiromaru, H.; Mitani, K.; Iwata, S.; Kimura, K., Photoelectron angular distribution and assignments of photoelectron spectra of nitrogen dioxide, nitromethane and nitrobenzene, Chem. Phys., 1982, 69, 423. [all data]

Allam, Migahed, et al., 1982
Allam, S.H.; Migahed, M.D.; El-Khodary, A., Electron impact ionization and dissociation of deuterated and non-deuterated methanol, methyl cyanide, nitromethane and nitrobenzene, Egypt. J. Phys., 1982, 13, 167. [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]

Asbrink, Svensson, et al., 1981
Asbrink, L.; Svensson, A.; Von Niessen, W.; Bieri, G., 30.4 nm He(II) photoelectron spectra of organic molecules, J. Electron Spectrosc. Relat. Phenom., 1981, 24, 293. [all data]

Allam, Migahed, et al., 1981
Allam, S.H.; Migahed, M.D.; El Khodary, A., Electron impact study of nitrobenzene and nitromethane, Int. J. Mass Spectrom. Ion Phys., 1981, 39, 117. [all data]

Rabalais, 1972
Rabalais, J.W., Photoelectron spectroscopic investigation of the electronic structure of nitromethane and nitrobenzene, J. Chem. Phys., 1972, 57, 960. [all data]

Nicholson, 1970
Nicholson, A.J.C., Determination of bond dissociation energies from photoionization efficiency curves in Recent Developments in Mass Spectrometroscopy, ed. K Ogata and T. Hayakawa, Univ. Park Press, Baltimore, MD, 1970, 745. [all data]

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Dewar, M.J.S.; Shanshal, M.; Worley, S.D., Calculated and observed ionization potentials gf nitroalkanes and of nitrous and nitric acids and esters. Extension of the MINDO method to nitrogen-oxygen compounds, J. Am. Chem. Soc., 1969, 91, 3590. [all data]

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Kandel, R.J., Appearance potential studies. II. Nitromethane, J. Chem. Phys., 1955, 23, 84. [all data]

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Haney, M.A.; Franklin, J.L., Correlation of excess energies of electron-impact dissociations with the translational energies of the products, J.Chem. Phys., 1968, 48, 4093. [all data]

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Tsuda, S.; Hamill, W.H., Ionization efficiency measurements by the retarding potential difference method, Advan. Mass Spectrom., 1966, 3, 249. [all data]

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Niwa, Y.; Tajima, S.; Tsuchiya, T., Fragmentation of energy-selected nitromethane ions, Int. J. Mass Spectrom. Ion Processes, 1981, 40, 287. [all data]

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Metz, Cyr, et al., 1991
Metz, R.B.; Cyr, D.R.; Neumark, D.M., Study of the 2B1 and 2A2 States of CH2NO2 via Ultraviolet Photoelectron Spectroscopy of the CH2NO2- Anion, J. Phys. Chem., 1991, 95, 7, 2900, https://doi.org/10.1021/j100160a047 . [all data]

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Bartmess, J.E.; Scott, J.A.; McIver, R.T., Jr., The gas phase acidity scale from methanol to phenol, J. Am. Chem. Soc., 1979, 101, 6047. [all data]

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MacKay, G.I.; Bohme, D.K., Proton-Transfer Reactions in Nitromethane at 297K, Int. J. Mass Spectrom. Ion Phys., 1978, 26, 4, 327, https://doi.org/10.1016/0020-7381(78)80052-7 . [all data]

Notes

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

• Symbols used in this document:
  

  AE	Appearance energy
  Cp,liquid	Constant pressure heat capacity of liquid
  EA	Electron affinity
  IE (evaluated)	Recommended ionization energy
  Pc	Critical pressure
  S°liquid	Entropy of liquid at standard conditions
  Tboil	Boiling point
  Tc	Critical temperature
  Tfus	Fusion (melting) point
  Ttriple	Triple point temperature
  d(ln(kH))/d(1/T)	Temperature dependence parameter for Henry's Law constant
  k°H	Henry's Law constant at 298.15K
  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
  ΔfusH	Enthalpy of fusion
  ΔfusS	Entropy of fusion
  ΔrG°	Free energy of reaction at standard conditions
  ΔrH°	Enthalpy of reaction at standard conditions
  ΔvapH	Enthalpy of vaporization
  ΔvapH°	Enthalpy of vaporization at standard conditions
  ΔvapS	Entropy of vaporization
  ρc	Critical density

• Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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