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
• Permanent link for this species. Use this link for bookmarking this species for future reference.
• Information on this page:
  • Condensed phase thermochemistry data
  • Phase change data
  • Reaction thermochemistry data
  • Henry's Law data
  • References
  • Notes
• Other data available:
  • Gas phase thermochemistry data
  • Gas phase ion energetics 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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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

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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:
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) (kJ/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 (bar)
    T = temperature (K)

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Enthalpy of fusion

Entropy of fusion

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
M - 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

CH₂NO₂^- +  =

By formula: CH₂NO₂^- + H⁺ = CH₃NO₂

 +  = ( • )

By formula: Cl^- + CH₃NO₂ = (Cl^- • CH₃NO₂)

( • ) +  = ( • 2)

By formula: (Cl^- • CH₃NO₂) + CH₃NO₂ = (Cl^- • 2CH₃NO₂)

 +  = ( • )

By formula: NO₂^- + CH₃NO₂ = (NO₂^- • CH₃NO₂)

C₆H₇N⁺ +  = (C₆H₇N⁺ • )

By formula: C₆H₇N⁺ + CH₃NO₂ = (C₆H₇N⁺ • CH₃NO₂)

Free energy of reaction

(CH₃NO₂^- • ) +  = (CH₃NO₂^- • 2)

By formula: (CH₃NO₂^- • CH₃NO₂) + CH₃NO₂ = (CH₃NO₂^- • 2CH₃NO₂)

CH₆N⁺ +  = (CH₆N⁺ • )

By formula: CH₆N⁺ + CH₃NO₂ = (CH₆N⁺ • CH₃NO₂)

Bond type: Hydrogen bonds of the type NH+-O between organics

CH₂NO₂^- +  = C₂H₅N₂O₄^-

By formula: CH₂NO₂^- + CH₃NO₂ = C₂H₅N₂O₄^-

C₃H₉N₃O₆^- + 3 = C₄H₁₂N₄O₈^-

By formula: C₃H₉N₃O₆^- + 3CH₃NO₂ = C₄H₁₂N₄O₈^-

C₂H₅N₂O₄^- + 2 = C₃H₈N₃O₆^-

By formula: C₂H₅N₂O₄^- + 2CH₃NO₂ = C₃H₈N₃O₆^-

C₃H₈N₃O₆^- + 3 = C₄H₁₁N₄O₈^-

By formula: C₃H₈N₃O₆^- + 3CH₃NO₂ = C₄H₁₁N₄O₈^-

C₄H₁₁N₄O₈^- + 4 = C₅H₁₄N₅O₁₀^-

By formula: C₄H₁₁N₄O₈^- + 4CH₃NO₂ = C₅H₁₄N₅O₁₀^-

C₂H₆N₂O₆^- + 2 = C₃H₉N₃O₈^-

By formula: C₂H₆N₂O₆^- + 2CH₃NO₂ = C₃H₉N₃O₈^-

C₄H₁₂N₄O₈^- + 4 = C₅H₁₅N₅O₁₀^-

By formula: C₄H₁₂N₄O₈^- + 4CH₃NO₂ = C₅H₁₅N₅O₁₀^-

C₃H₉N₃O₈^- + 3 = C₄H₁₂N₄O₁₀^-

By formula: C₃H₉N₃O₈^- + 3CH₃NO₂ = C₄H₁₂N₄O₁₀^-

CH₃N₂O₄^- + 2 = C₂H₆N₃O₆^-

By formula: CH₃N₂O₄^- + 2CH₃NO₂ = C₂H₆N₃O₆^-

C₂H₆ClN₂O₄^- + 3 = C₃H₉ClN₃O₆^-

By formula: C₂H₆ClN₂O₄^- + 3CH₃NO₂ = C₃H₉ClN₃O₆^-

C₁₁H₁₀⁺ +  = (C₁₁H₁₀⁺ • )

By formula: C₁₁H₁₀⁺ + CH₃NO₂ = (C₁₁H₁₀⁺ • CH₃NO₂)

C₂H₆N₃O₆^- + 3 = C₃H₉N₄O₈^-

By formula: C₂H₆N₃O₆^- + 3CH₃NO₂ = C₃H₉N₄O₈^-

C₃H₉N₄O₈^- + 4 = C₄H₁₂N₅O₁₀^-

By formula: C₃H₉N₄O₈^- + 4CH₃NO₂ = C₄H₁₂N₅O₁₀^-

C₅H₁₀NO₂⁺ +  = (C₅H₁₀NO₂⁺ • )

By formula: C₅H₁₀NO₂⁺ + CH₃NO₂ = (C₅H₁₀NO₂⁺ • CH₃NO₂)

C₅H₁₂NO₂⁺ +  = (C₅H₁₂NO₂⁺ • )

By formula: C₅H₁₂NO₂⁺ + CH₃NO₂ = (C₅H₁₂NO₂⁺ • CH₃NO₂)

C₃H₉ClN₃O₆^- + 4 = C₄H₁₂ClN₄O₈^-

By formula: C₃H₉ClN₃O₆^- + 4CH₃NO₂ = C₄H₁₂ClN₄O₈^-

C₄H₁₂N₄O₁₀^- + 4 = C₅H₁₅N₅O₁₂^-

By formula: C₄H₁₂N₄O₁₀^- + 4CH₃NO₂ = C₅H₁₅N₅O₁₂^-

 +  = ( • )

By formula: Li⁺ + CH₃NO₂ = (Li⁺ • CH₃NO₂)

CH₃NO₂^- +  = (CH₃NO₂^- • )

By formula: CH₃NO₂^- + CH₃NO₂ = (CH₃NO₂^- • CH₃NO₂)

 +  = CH₃BrNO₂^-

By formula: Br^- + CH₃NO₂ = CH₃BrNO₂^-

 +  = ( • )

By formula: I^- + CH₃NO₂ = (I^- • CH₃NO₂)

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)

References

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

Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

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]

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]

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]

Timmermans, 1952
Timmermans, J., Freezing points of organic compounds. VVI New determinations., Bull. Soc. Chim. Belg., 1952, 61, 393. [all data]

Dreisbach and Martin, 1949
Dreisbach, R.R.; Martin, R.A., Physical Data on Some Organic Compounds, Ind. Eng. Chem., 1949, 41, 2875-8. [all data]

Joukovsky, 1934
Joukovsky, N.I., Experimental Study of the Theory of Concentrated Solutions. XI. Thermodynamic Properties of Concentrated Solutions of Aliphatic Organic Compounds Containing Nitrogen., Bull. Soc. Chim. Belg., 1934, 43, 397. [all data]

Timmermans, 1921
Timmermans, J., The Freezing Points of Organic Substances IV. New Exp. Determinations, Bull. Soc. Chim. Belg., 1921, 30, 62. [all data]

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]

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]

Bartmess, Scott, et al., 1979
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]

Cumming and Kebarle, 1978
Cumming, J.B.; Kebarle, P., Summary of gas phase measurements involving acids AH. Entropy changes in proton transfer reactions involving negative ions. Bond dissociation energies D(A-H) and electron affinities EA(A), Can. J. Chem., 1978, 56, 1. [all data]

MacKay and Bohme, 1978
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]

Wincel, 2003
Wincel, H., Gas-phase Solvation of Cl-, NO2-, CH2NO2-, CH3NO2-, and CH3NO4- by CH3NO2, Int. J. Mass Spectrom., 2003, 226, 3, 341-353, https://doi.org/10.1016/S1387-3806(03)00066-6 . [all data]

Sieck, 1985
Sieck, L.W., Thermochemistry of Solvation of NO₂^- and C₆H₅NO₂^- by Polar Molecules in the Vapor Phase. Comparison with Cl^- and Variation with Ligand Structure., J. Phys. Chem., 1985, 89, 25, 5552, https://doi.org/10.1021/j100271a049 . [all data]

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Larson, J.W.; McMahon, T.B., Fluoride and chloride affinities of main group oxides, fluorides, oxofluorides, and alkyls. Quantitative scales of lewis acidities from ion cyclotron resonance halide-exchange equilibria, J. Phys. Chem., 1984, 88, 1083. [all data]

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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]

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]

El-Shall and Meot-Ner (Mautner), 1987
El-Shall, M.S.; Meot-Ner (Mautner), M., Ionic Charge Transfer Complexes. 3. Delocalised pi Systems as Electron Acceptors and Donors, J. Phys. Chem., 1987, 91, 5, 1088, https://doi.org/10.1021/j100289a017 . [all data]

Meot-Ner and Field, 1974
Meot-Ner, (Mautner); Field, F.H., Solvation and Association of Protonated Gaseous Amino Acids, J. Am. Chem. Soc., 1974, 96, 10, 3168, https://doi.org/10.1021/ja00817a024 . [all data]

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Staley, R.H.; Beauchamp, J.L., Intrinsic Acid - Base Properties of Molecules. Binding Energies of Li+ to pi - and n - Donor Bases, J. Am. Chem. Soc., 1975, 97, 20, 5920, https://doi.org/10.1021/ja00853a050 . [all data]

Dzidic and Kebarle, 1970
Dzidic, I.; Kebarle, P., Hydration of the Alkali Ions in the Gas Phase. Enthalpies and Entropies of Reactions M+(H2O)n-1 + H2O = M+(H2O)n, J. Phys. Chem., 1970, 74, 7, 1466, https://doi.org/10.1021/j100702a013 . [all data]

Tanabe, Morgon, et al., 1996
Tanabe, F.K.J.; Morgon, N.H.; Riveros, J.M., Relative Bromide and Iodide Affinity of Simple Solvent Molecules Determined by FT-ICR, J. Phys. Chem., 1996, 100, 8, 2862-2866, https://doi.org/10.1021/jp952290p . [all data]

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Hiraoka, K.; Mizure, S.; Yamabe, S.; Nakatsuji, Y., Gas Phase Clustering Reactions of CN^- and CH₂CN^- with MeCN, Chem. Phys. Lett., 1988, 148, 6, 497, https://doi.org/10.1016/0009-2614(88)80320-8 . [all data]

Caldwell, Masucci, et al., 1989
Caldwell, G.W.; Masucci, J.A.; Ikonomou, M.G., Negative Ion Chemical Ionization Mass Spectrometry - Binding of Molecules to Bromide and Iodide Anions, Org. Mass Spectrom., 1989, 24, 1, 8, https://doi.org/10.1002/oms.1210240103 . [all data]

Notes

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

• Symbols used in this document:
  

  Cp,liquid	Constant pressure heat capacity of liquid
  Pc	Critical pressure
  S°liquid	Entropy of liquid at standard conditions
  T	Temperature
  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°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
  ΔrS°	Entropy 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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