Methyl Alcohol

• Formula: CH₄O
• Molecular weight: 32.0419
• IUPAC Standard InChI: InChI=1S/CH4O/c1-2/h2H,1H3 Copy

  
• IUPAC Standard InChIKey: OKKJLVBELUTLKV-UHFFFAOYSA-N Copy
• CAS Registry Number: 67-56-1
• 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.
• Isotopologues:
  • Methan-d3-ol
  • Methanol-o-d1
  • Methanol-D4
• Other names: Methanol; Carbinol; Methyl hydroxide; Methylol; Monohydroxymethane; Wood alcohol; CH3OH; Colonial spirit; Columbian spirit; Hydroxymethane; Wood naphtha; Alcool methylique; Alcool metilico; Columbian spirits; Metanolo; Methylalkohol; Metylowy alkohol; Pyroxylic spirit; Wood spirit; Rcra waste number U154; UN 1230; Pyro alcohol; Spirit of wood; Bieleski's solution; NSC 85232
• Permanent link for this species. Use this link for bookmarking this species for future reference.
• Information on this page:
  • Reaction thermochemistry data (reactions 51 to 100)
  • References
  • Notes
• Other data available:
  • Gas phase thermochemistry data
  • Condensed phase thermochemistry data
  • Phase change data
  • Reaction thermochemistry data: reactions 1 to 50, reactions 101 to 150, reactions 151 to 200, reactions 201 to 250, reactions 251 to 300
  • Henry's Law data
  • Gas phase ion energetics data
  • Ion clustering data
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • Vibrational and/or electronic energy levels
  • Gas Chromatography
  • Fluid Properties
• Data at other public NIST sites:
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  • Gas Phase Kinetics Database
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Reaction thermochemistry data

Go To: Top, 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:
B - John E. Bartmess
M - Michael M. Meot-Ner (Mautner) and Sharon G. Lias
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
MS - José A. Martinho Simões

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.

Reactions 51 to 100

( • 9) +  = ( • 10)

By formula: (Br^- • 9CH₄O) + CH₄O = (Br^- • 10CH₄O)

( • 7) +  = ( • 8)

By formula: (I^- • 7CH₄O) + CH₄O = (I^- • 8CH₄O)

( • 8) +  = ( • 9)

By formula: (Br^- • 8CH₄O) + CH₄O = (Br^- • 9CH₄O)

C₂H^- +  = C₃H₅O^-

By formula: C₂H^- + CH₄O = C₃H₅O^-

C₉H₇^- +  = C₁₀H₁₁O^-

By formula: C₉H₇^- + CH₄O = C₁₀H₁₁O^-

C₆H₉^- +  = C₇H₁₃O^-

By formula: C₆H₉^- + CH₄O = C₇H₁₃O^-

C₇H₄N₂O₂^- +  = (C₇H₄N₂O₂^- • )

By formula: C₇H₄N₂O₂^- + CH₄O = (C₇H₄N₂O₂^- • CH₄O)

C₆H₄FNO₂^- +  = (C₆H₄FNO₂^- • )

By formula: C₆H₄FNO₂^- + CH₄O = (C₆H₄FNO₂^- • CH₄O)

C₇H₇NO₃^- +  = (C₇H₇NO₃^- • )

By formula: C₇H₇NO₃^- + CH₄O = (C₇H₇NO₃^- • CH₄O)

 +  =  + 2

By formula: C₅H₁₂O₄ + H₂O = C₃H₆O₃ + 2CH₄O

 +  =  + 2

By formula: C₆H₁₄O₃ + H₂O = C₄H₈O₂ + 2CH₄O

(CH₅O⁺ • 10) +  = (CH₅O⁺ • 11)

By formula: (CH₅O⁺ • 10CH₄O) + CH₄O = (CH₅O⁺ • 11CH₄O)

Bond type: Hydrogen bonds of the type OH-O between organics

Free energy of reaction

(CH₅O⁺ • 11) +  = (CH₅O⁺ • 12)

By formula: (CH₅O⁺ • 11CH₄O) + CH₄O = (CH₅O⁺ • 12CH₄O)

Bond type: Hydrogen bonds of the type OH-O between organics

Free energy of reaction

(CH₅O⁺ • 12) +  = (CH₅O⁺ • 13)

By formula: (CH₅O⁺ • 12CH₄O) + CH₄O = (CH₅O⁺ • 13CH₄O)

Bond type: Hydrogen bonds of the type OH-O between organics

Free energy of reaction

(CH₅O⁺ • 9) +  = (CH₅O⁺ • 10)

By formula: (CH₅O⁺ • 9CH₄O) + CH₄O = (CH₅O⁺ • 10CH₄O)

Bond type: Hydrogen bonds of the type OH-O between organics

Free energy of reaction

(CH₅O⁺ • 8) +  = (CH₅O⁺ • 9)

By formula: (CH₅O⁺ • 8CH₄O) + CH₄O = (CH₅O⁺ • 9CH₄O)

Bond type: Hydrogen bonds of the type OH-O between organics

Free energy of reaction

 +  = CH₃D₄FO^-

By formula: F^- + CH₄O = CH₃D₄FO^-

( • 2) +  = ( • 3)

By formula: (O₂^- • 2CH₄O) + CH₄O = (O₂^- • 3CH₄O)

( • ) +  = ( • 2)

By formula: (O₂^- • CH₄O) + CH₄O = (O₂^- • 2CH₄O)

( • 10) +  = ( • 11)

By formula: (F^- • 10CH₄O) + CH₄O = (F^- • 11CH₄O)

( • 9) +  = ( • 10)

By formula: (Cl^- • 9CH₄O) + CH₄O = (Cl^- • 10CH₄O)

( • 3) +  = ( • 4)

By formula: (F^- • 3CH₄O) + CH₄O = (F^- • 4CH₄O)

( • 4) +  = ( • 5)

By formula: (F^- • 4CH₄O) + CH₄O = (F^- • 5CH₄O)

( • 5) +  = ( • 6)

By formula: (F^- • 5CH₄O) + CH₄O = (F^- • 6CH₄O)

( • 9) +  = ( • 10)

By formula: (F^- • 9CH₄O) + CH₄O = (F^- • 10CH₄O)

( • 5) +  = ( • 6)

By formula: (Cl^- • 5CH₄O) + CH₄O = (Cl^- • 6CH₄O)

( • 6) +  = ( • 7)

By formula: (Cl^- • 6CH₄O) + CH₄O = (Cl^- • 7CH₄O)

( • 7) +  = ( • 8)

By formula: (Cl^- • 7CH₄O) + CH₄O = (Cl^- • 8CH₄O)

( • 8) +  = ( • 9)

By formula: (Cl^- • 8CH₄O) + CH₄O = (Cl^- • 9CH₄O)

( • 6) +  = ( • 7)

By formula: (F^- • 6CH₄O) + CH₄O = (F^- • 7CH₄O)

( • 7) +  = ( • 8)

By formula: (F^- • 7CH₄O) + CH₄O = (F^- • 8CH₄O)

( • 8) +  = ( • 9)

By formula: (F^- • 8CH₄O) + CH₄O = (F^- • 9CH₄O)

( • 3) +  = ( • 4)

By formula: (I^- • 3CH₄O) + CH₄O = (I^- • 4CH₄O)

( • 4) +  = ( • 5)

By formula: (I^- • 4CH₄O) + CH₄O = (I^- • 5CH₄O)

( • 5) +  = ( • 6)

By formula: (I^- • 5CH₄O) + CH₄O = (I^- • 6CH₄O)

( • 6) +  = ( • 7)

By formula: (I^- • 6CH₄O) + CH₄O = (I^- • 7CH₄O)

( • 3) +  = ( • 4)

By formula: (Br^- • 3CH₄O) + CH₄O = (Br^- • 4CH₄O)

( • 4) +  = ( • 5)

By formula: (Br^- • 4CH₄O) + CH₄O = (Br^- • 5CH₄O)

( • 5) +  = ( • 6)

By formula: (Br^- • 5CH₄O) + CH₄O = (Br^- • 6CH₄O)

( • 6) +  = ( • 7)

By formula: (Br^- • 6CH₄O) + CH₄O = (Br^- • 7CH₄O)

( • 7) +  = ( • 8)

By formula: (Br^- • 7CH₄O) + CH₄O = (Br^- • 8CH₄O)

 +  =

By formula: C₅H₁₀ + CH₄O = C₆H₁₄O

(C₂H₇O⁺ • 2 • ) +  = (C₂H₇O⁺ • 3 • )

By formula: (C₂H₇O⁺ • 2CH₄O • C₂H₆O) + CH₄O = (C₂H₇O⁺ • 3CH₄O • C₂H₆O)

Bond type: Hydrogen bonds of the type OH-O between organics

(C₂H₇O⁺ •  • ) +  = (C₂H₇O⁺ • 2 • )

By formula: (C₂H₇O⁺ • CH₄O • C₂H₆O) + CH₄O = (C₂H₇O⁺ • 2CH₄O • C₂H₆O)

Bond type: Hydrogen bonds of the type OH-O between organics

C₁₆H₃₄OP₂Ru (solution) +  (solution) = C₁₇H₃₆OP₂Ru (solution) +  (solution)

By formula: C₁₆H₃₄OP₂Ru (solution) + CH₄O (solution) = C₁₇H₃₆OP₂Ru (solution) + H₂O (solution)

 +  = ( • )

By formula: NO₂^- + CH₄O = (NO₂^- • CH₄O)

 +  = ( • )

By formula: O₂^- + CH₄O = (O₂^- • CH₄O)

 +  = ( • )

By formula: CHO₂^- + CH₄O = (CHO₂^- • CH₄O)

(C₂H₇O⁺ • 2) +  = (C₂H₇O⁺ •  • 2)

By formula: (C₂H₇O⁺ • 2CH₄O) + C₂H₆O = (C₂H₇O⁺ • C₂H₆O • 2CH₄O)

Bond type: Hydrogen bonds of the type OH-O between organics

(C₂H₇O⁺ • 3) +  = (C₂H₇O⁺ •  • 3)

By formula: (C₂H₇O⁺ • 3CH₄O) + C₂H₆O = (C₂H₇O⁺ • C₂H₆O • 3CH₄O)

Bond type: Hydrogen bonds of the type OH-O between organics

References

Go To: Top, Reaction thermochemistry data, Notes

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

Hiraoka and Yamabe, 1991
Hiraoka, K.; Yamabe, S., Solvation of Halide Ions with CH3OH in the gas Phase, Int. J. Mass Spectrom. Ion Proc., 1991, 109, 133, https://doi.org/10.1016/0168-1176(91)85101-Q . [all data]

Chabinyc and Brauman, 1999
Chabinyc, M.L.; Brauman, J.I., Hydrogen bond strength and acidity. Structural and energetic correlations for acetylides and alcohols, J. Phys. Chem. A, 1999, 103, 46, 9163-9166, https://doi.org/10.1021/jp992852v . [all data]

Mustanir, Matsuoka, et al., 2006
Mustanir; Matsuoka, M.; Mishima, M.; Koch, H., Stability of complexes of phenylacetylides and benzyl alkoxides with methanol in the gas phase. Acid-base correlation in the ionic hydrogen-bond strength, Bull. Chem. Soc. Japan, 2006, 79, 7, 1118-1125, https://doi.org/10.1246/bcsj.79.1118 . [all data]

Chowdhury, Grimsrud, et al., 1987
Chowdhury, S.; Grimsrud, E.P.; Kebarle, P., Bonding of Charged Delocalized Anions to Protic and Dipolar Aprotic Solvent Molecules, J. Phys. Chem., 1987, 91, 10, 2551, https://doi.org/10.1021/j100294a021 . [all data]

Chowdhury, 1987
Chowdhury, S. Grimsrud, Bonding of Charge Delocalized Anions to Protic and Dipolar Aprotic Solvents, J. Phys. Chem., 1987, 91, 10, 2551, https://doi.org/10.1021/j100294a021 . [all data]

Wiberg, 1980
Wiberg, K.B., Energies of organic compounds, Rept. DOE-E(11-1)4060 Prepared for US Dept. of Energy by Yale Univ., New Haven, CT. Avail. NTIS, 1980, 1-24. [all data]

Wiberg and Squires, 1979
Wiberg, K.B.; Squires, R.R., A microprocessor-controlled system for precise measurement of temperature changes. Determination of the enthalpies of hydrolysis of some polyoxygenated hydrocarbons, J. Chem. Thermodyn., 1979, 11, 773-786. [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]

Wiberg, Martin, et al., 1985
Wiberg, K.B.; Martin, E.J.; Squires, R.R., Thermochemical studies of carbonyl compounds. 3. Enthalpies of hydrolysis of ortho esters, J. Org. Chem., 1985, 50, 4717-4720. [all data]

Guthrie and Cullimore, 1980
Guthrie, J.P.; Cullimore, P.A., Effect of the acyl substituent on the equilibrium constant for hydration of esters, Can. J. Chem., 1980, 58, 1281-1294. [all data]

Meot-Ner (Mautner), 1992
Meot-Ner (Mautner), M., Intermolecular Forces in Organic Clusters, J. Am. Chem. Soc., 1992, 114, 9, 3312, https://doi.org/10.1021/ja00035a024 . [all data]

Wilkinson, Szulejko, et al., 1992
Wilkinson, F.E.; Szulejko, J.E.; Allison, C.E.; Mcmahon, T.B., Fourier Transform Ion Cyclotron Resonance Investigation of the Deuterium Isotope Effect on Gas Phase Ion/Molecule Hydrogen Bonding Interactions in Alcohol-Fluoride Adduct Ions, Int. J. Mass Spectrom., 1992, 117, 487-505, https://doi.org/10.1016/0168-1176(92)80110-M . [all data]

Yamdagni, Payzant, et al., 1973
Yamdagni, R.; Payzant, J.D.; Kebarle, P., Solvation of Cl- and O₂- with H₂O, CH₃OH, and CH₃CN in the gas phase, Can. J. Chem., 1973, 51, 2507. [all data]

Hiraoka and Mizuse, 1987
Hiraoka, K.; Mizuse, S., Gas-Phase Solvation of Cl- with H2O, CH3OH, C2H4OH, i-C3H7OH, n-C3H7OH, and t-C4H9OH, Chem. Phys., 1987, 118, 3, 457, https://doi.org/10.1016/0301-0104(87)85078-4 . [all data]

Serda, Izquierdo, et al., 1995
Serda, J.A.; Izquierdo, J.F.; Tejero, J.; Cunill, F.; Iborra, M., Equilibrium and thermodynamics for 2-methyl-2-methoxybutane liquid-phase decomposition, Thermochim. Acta, 1995, 259, 111-120. [all data]

Hwang and Wu, 1994
Hwang, W.-S.; Wu, J.-C., Kinetics and thermodynamics of synthesis of tertiary-amyl methyl ether catalyzed by ion-exchange resin, J. Chin. Chem. Soc. (Taipei), 1994, 41, 181-186. [all data]

Rihko, Linnekoski, et al., 1994
Rihko, L.K.; Linnekoski, J.A.; Krause, A.O., Reaction equilibria in the synthesis of 2-methoxy-2-methylbutane and 2-ethyoxy-2-methylbutane in the liquid phase, J. Chem. Eng. Data, 1994, 39, 700-704. [all data]

Hiraoka, Grimsrud, et al., 1974
Hiraoka, K.; Grimsrud, E.P.; Kebarle, P., Gas Phase Ion Equilibria Studies of the Hydrogen Ion in Water - Dimethyl Ether and Methanol - Dimethyl Ether Mixtures, J. Am. Chem. Soc., 1974, 96, 11, 3359, https://doi.org/10.1021/ja00818a004 . [all data]

Bryndza, Fong, et al., 1987
Bryndza, H.E.; Fong, L.K.; Paciello, R.A.; Tam, W.; Bercaw, J.E., J. Am. Chem. Soc., 1987, 109, 1444. [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]

Meot-Ner and Sieck, 1986
Meot-Ner, M.; Sieck, L.W., The ionic hydrogen bond and ion solvation. 5. OH...O^- bonds. Gas phase solvation and clustering of alkoxide and carboxylate anions, J. Am. Chem. Soc., 1986, 108, 7525. [all data]

Notes

Go To: Top, Reaction thermochemistry data, References

• Symbols used in this document:
  

  T	Temperature
  ΔrG°	Free energy of reaction at standard conditions
  ΔrH°	Enthalpy of reaction at standard conditions
  ΔrS°	Entropy of reaction at standard conditions

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