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 101 to 150)
  • References
  • Notes
• Other data available:
  • Gas phase thermochemistry data
  • Condensed phase thermochemistry data
  • Phase change data
  • Reaction thermochemistry data: reactions 1 to 50, reactions 51 to 100, 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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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:
M - Michael M. Meot-Ner (Mautner) and Sharon G. Lias
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.

Reactions 101 to 150

(CH₅O⁺ •  • ) +  = (CH₅O⁺ • 2 • )

By formula: (CH₅O⁺ • CH₄O • H₂O) + CH₄O = (CH₅O⁺ • 2CH₄O • H₂O)

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

 +  = ( • )

By formula: C₄H₄N^- + CH₄O = (C₄H₄N^- • CH₄O)

(C₂H₇O⁺ • ) +  = (C₂H₇O⁺ •  • )

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

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

(C₂H₇O⁺ • ) +  = (C₂H₇O⁺ •  • )

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

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

(C₂H₄N⁺ •  • ) +  = (C₂H₄N⁺ • 2 • )

By formula: (C₂H₄N⁺ • CH₄O • C₂H₃N) + CH₄O = (C₂H₄N⁺ • 2CH₄O • C₂H₃N)

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

(CH₅O⁺ • 2 • 2) +  = (CH₅O⁺ • 3 • 2)

By formula: (CH₅O⁺ • 2H₂O • 2CH₄O) + H₂O = (CH₅O⁺ • 3H₂O • 2CH₄O)

Bond type: Hydrogen bond (positive ion to hydride)

(CH₅O⁺ •  • 2) +  = (CH₅O⁺ • 2 • 2)

By formula: (CH₅O⁺ • H₂O • 2CH₄O) + H₂O = (CH₅O⁺ • 2H₂O • 2CH₄O)

Bond type: Hydrogen bond (positive ion to hydride)

(CH₅O⁺ • 2 • ) +  = (CH₅O⁺ • 3 • )

By formula: (CH₅O⁺ • 2H₂O • CH₄O) + H₂O = (CH₅O⁺ • 3H₂O • CH₄O)

Bond type: Hydrogen bond (positive ion to hydride)

(CH₅O⁺ • 2) +  = (CH₅O⁺ •  • 2)

By formula: (CH₅O⁺ • 2H₂O) + CH₄O = (CH₅O⁺ • CH₄O • 2H₂O)

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

(CH₅O⁺ • 3 • ) +  = (CH₅O⁺ • 4 • )

By formula: (CH₅O⁺ • 3H₂O • CH₄O) + H₂O = (CH₅O⁺ • 4H₂O • CH₄O)

Bond type: Hydrogen bond (positive ion to hydride)

(CH₅O⁺ •  • 3) +  = (CH₅O⁺ • 2 • 3)

By formula: (CH₅O⁺ • H₂O • 3CH₄O) + H₂O = (CH₅O⁺ • 2H₂O • 3CH₄O)

Bond type: Hydrogen bond (positive ion to hydride)

( • 2) +  = ( •  • 2)

By formula: (K⁺ • 2H₂O) + CH₄O = (K⁺ • CH₄O • 2H₂O)

( •  • ) +  = ( • 2 • )

By formula: (Cl^- • H₂O • CH₄O) + H₂O = (Cl^- • 2H₂O • CH₄O)

Bond type: Hydrogen bond (negative ion to hydride)

(CH₃O^- •  • ) +  = (CH₃O^- • 2 • )

By formula: (CH₃O^- • H₂O • CH₄O) + H₂O = (CH₃O^- • 2H₂O • CH₄O)

Bond type: Hydrogen bond (negative ion to hydride)

(C₂H₇O⁺ • 2) +  = (C₂H₇O⁺ • 3)

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

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

(C₂H₇O⁺ • 3) +  = (C₂H₇O⁺ • 4)

By formula: (C₂H₇O⁺ • 3CH₄O) + CH₄O = (C₂H₇O⁺ • 4CH₄O)

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

(C₂H₇O⁺ • ) +  = (C₂H₇O⁺ • 2)

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

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

(C₄H₁₁O₂⁺ • 2) +  = (C₄H₁₁O₂⁺ • 3)

By formula: (C₄H₁₁O₂⁺ • 2CH₄O) + CH₄O = (C₄H₁₁O₂⁺ • 3CH₄O)

Bond type: Hydrogen bonds between protonated and neutral organics

(C₄H₁₁O₂⁺ • 3) +  = (C₄H₁₁O₂⁺ • 4)

By formula: (C₄H₁₁O₂⁺ • 3CH₄O) + CH₄O = (C₄H₁₁O₂⁺ • 4CH₄O)

Bond type: Hydrogen bonds between protonated and neutral organics

(C₄H₁₁O₂⁺ • 4) +  = (C₄H₁₁O₂⁺ • 5)

By formula: (C₄H₁₁O₂⁺ • 4CH₄O) + CH₄O = (C₄H₁₁O₂⁺ • 5CH₄O)

Bond type: Hydrogen bonds between protonated and neutral organics

(C₄H₁₁O₂⁺ • 5) +  = (C₄H₁₁O₂⁺ • 6)

By formula: (C₄H₁₁O₂⁺ • 5CH₄O) + CH₄O = (C₄H₁₁O₂⁺ • 6CH₄O)

Bond type: Hydrogen bonds between protonated and neutral organics

(C₄H₁₁O₂⁺ • ) +  = (C₄H₁₁O₂⁺ • 2)

By formula: (C₄H₁₁O₂⁺ • CH₄O) + CH₄O = (C₄H₁₁O₂⁺ • 2CH₄O)

Bond type: Hydrogen bonds between protonated and neutral organics

(C₃H₁₀N⁺ • ) +  = (C₃H₁₀N⁺ •  • )

By formula: (C₃H₁₀N⁺ • C₃H₉N) + CH₄O = (C₃H₁₀N⁺ • CH₄O • C₃H₉N)

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

C₇H₄F₃NO₂^- +  = (C₇H₄F₃NO₂^- • )

By formula: C₇H₄F₃NO₂^- + CH₄O = (C₇H₄F₃NO₂^- • CH₄O)

(CH₅O⁺ • 3) +  = (CH₅O⁺ •  • 3)

By formula: (CH₅O⁺ • 3CH₄O) + H₂O = (CH₅O⁺ • H₂O • 3CH₄O)

Bond type: Hydrogen bond (positive ion to hydride)

(CH₅O⁺ • 4) +  = (CH₅O⁺ •  • 4)

By formula: (CH₅O⁺ • 4CH₄O) + H₂O = (CH₅O⁺ • H₂O • 4CH₄O)

Bond type: Hydrogen bond (positive ion to hydride)

(CH₃O^- • 2) +  = (CH₃O^- •  • 2)

By formula: (CH₃O^- • 2CH₄O) + H₂O = (CH₃O^- • H₂O • 2CH₄O)

Bond type: Hydrogen bond (negative ion to hydride)

(CH₅O⁺ • ) +  = (CH₅O⁺ •  • )

By formula: (CH₅O⁺ • CH₄O) + H₂O = (CH₅O⁺ • H₂O • CH₄O)

Bond type: Hydrogen bond (positive ion to hydride)

( • ) +  = ( •  • )

By formula: (Cl^- • CH₄O) + H₂O = (Cl^- • H₂O • CH₄O)

Bond type: Hydrogen bond (negative ion to hydride)

(CH₃O^- • ) +  = (CH₃O^- •  • )

By formula: (CH₃O^- • CH₄O) + H₂O = (CH₃O^- • H₂O • CH₄O)

Bond type: Hydrogen bond (negative ion to hydride)

(C₂H₄N⁺ • 2) +  = (C₂H₄N⁺ • 3)

By formula: (C₂H₄N⁺ • 2CH₄O) + CH₄O = (C₂H₄N⁺ • 3CH₄O)

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

(C₃H₁₀N⁺ • 2) +  = (C₃H₁₀N⁺ • 3)

By formula: (C₃H₁₀N⁺ • 2CH₄O) + CH₄O = (C₃H₁₀N⁺ • 3CH₄O)

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

( • 2) +  = ( •  • 2)

By formula: (Cl^- • 2CH₄O) + H₂O = (Cl^- • H₂O • 2CH₄O)

Bond type: Hydrogen bond (negative ion to hydride)

 +  = 2 + 

By formula: C₅H₁₂O₃ + H₂O = 2CH₄O + C₃H₆O₂

(C₂H₄N⁺ • ) +  = (C₂H₄N⁺ • 2)

By formula: (C₂H₄N⁺ • CH₄O) + CH₄O = (C₂H₄N⁺ • 2CH₄O)

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

(C₃H₁₀N⁺ • ) +  = (C₃H₁₀N⁺ • 2)

By formula: (C₃H₁₀N⁺ • CH₄O) + CH₄O = (C₃H₁₀N⁺ • 2CH₄O)

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

C₁₀H₂₁O₅⁺ +  = (C₁₀H₂₁O₅⁺ • )

By formula: C₁₀H₂₁O₅⁺ + CH₄O = (C₁₀H₂₁O₅⁺ • CH₄O)

Bond type: Hydrogen bonds with polydentate bonding in positive ions

C₁₂H₂₅O₆⁺ +  = (C₁₂H₂₅O₆⁺ • )

By formula: C₁₂H₂₅O₆⁺ + CH₄O = (C₁₂H₂₅O₆⁺ • CH₄O)

Bond type: Hydrogen bonds with polydentate bonding in positive ions

C₂H₇O⁺ +  = (C₂H₇O⁺ • )

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

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

C₈H₁₇O₄⁺ +  = (C₈H₁₇O₄⁺ • )

By formula: C₈H₁₇O₄⁺ + CH₄O = (C₈H₁₇O₄⁺ • CH₄O)

Bond type: Hydrogen bonds with polydentate bonding in positive ions

 +  =  + 2

By formula: C₇H₁₆O₃ + H₂O = C₅H₁₀O₂ + 2CH₄O

 +  =  + 2

By formula: C₈H₁₈O₃ + H₂O = C₆H₁₂O₂ + 2CH₄O

 +  =  + 2

By formula: C₈H₁₈O₃ + H₂O = C₆H₁₂O₂ + 2CH₄O

C₄H₁₁O₂⁺ +  = (C₄H₁₁O₂⁺ • )

By formula: C₄H₁₁O₂⁺ + CH₄O = (C₄H₁₁O₂⁺ • CH₄O)

Bond type: Hydrogen bonds between protonated and neutral organics

(CH₅O⁺ • 7) +  = (CH₅O⁺ • 8)

By formula: (CH₅O⁺ • 7CH₄O) + CH₄O = (CH₅O⁺ • 8CH₄O)

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

 +  =  + 2

By formula: C₉H₂₀O₂ + H₂O = C₇H₁₄O + 2CH₄O

 +  = ( • )

By formula: C₆H₁₁NO₃ + CH₄O = (C₆H₁₁NO₃ • CH₄O)

Free energy of reaction

C₃H₇O⁺ +  = (C₃H₇O⁺ • )

By formula: C₃H₇O⁺ + CH₄O = (C₃H₇O⁺ • CH₄O)

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

C₃H₁₀N⁺ +  = (C₃H₁₀N⁺ • )

By formula: C₃H₁₀N⁺ + CH₄O = (C₃H₁₀N⁺ • CH₄O)

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

 +  = ( • )

By formula: K⁺ + CH₄O = (K⁺ • CH₄O)

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.

Meot-Ner(Mautner), 1986
Meot-Ner(Mautner), M., Comparative Stabilities of Cationic and Anionic Hydrogen-Bonded Networks. Mixed Clusters of Water-Methanol, J. Am. Chem. Soc., 1986, 108, 20, 6189, https://doi.org/10.1021/ja00280a014 . [all data]

Meot-ner, 1988
Meot-ner, M., The Ionic Hydrogen Bond and Solvation. 7. Interaction Energies of Carbanions with Solvent Molecules, J. Am. Chem. Soc., 1988, 110, 12, 3858, https://doi.org/10.1021/ja00220a022 . [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]

El-Shall, Olafsdottir, et al., 1991
El-Shall, M.S.; Olafsdottir, S.; Meot-ner (Mautner), M.; Sieck, L.W., Energy effects on cluster ion distributions: Beam expansion and thermochemical studies on mixed clusters of methanol and acetonitrile, Chem. Phys. Lett., 1991, 185, 3-4, 193, https://doi.org/10.1016/S0009-2614(91)85046-Y . [all data]

Evans and Keesee, 1991
Evans, D.H.; Keesee, R.G., Thermodynamics of Gas-Phase Mixed-Solvent Cluster Ions - Water and Methanol on K+ and Cl- and Comparison to Liquid Solutions, J. Phys. Chem., 1991, 95, 9, 3558, https://doi.org/10.1021/j100162a024 . [all data]

Meot-Ner (Mautner), Sieck, et al., 1994
Meot-Ner (Mautner), M.; Sieck, L.W.; Liebman, J.F.; Scheiner, S.; Duan, X., The Ionic Hydrogen Bond. 5. Polydentate and Solvent-Bridged Structures. Complexing of the Proton and the Hydronium Ions by Polyethers, J. Am. Chem. Soc., 1994, 116, 17, 7848, https://doi.org/10.1021/ja00096a047 . [all data]

El-Shall, Daly, et al., 1992
El-Shall, M.S.; Daly, G.M.; Gao, J.; Meot-Ner (Mautner), M.; Sieck, L.W., How Sensitive are Cluster Compositions to Energetics? A Joint Beam Expansion/ Thermochemical Study of Water - Methanol - Trimethylamine Clusters, J. Phys. Chem., 1992, 96, 2, 507, https://doi.org/10.1021/j100181a002 . [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]

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]

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]

Sharma and Kebarle, 1984
Sharma, R.B.; Kebarle, P., Stabilites and Hydrogen Bonding in Complexes of H3O+ and CH3OH2+ with Crown Ethers, from Measurements of Gas - Phase Ion - Molecule Equilibria, J. Am. Chem. Soc., 1984, 106, 14, 3913, https://doi.org/10.1021/ja00326a005 . [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]

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]

Wiberg and Squires, 1979, 2
Wiberg, K.B.; Squires, R.R., Thermodynamics of hydrolysis aliphatic ketals. An entropy component of steric effects, J. Am. Chem. Soc., 1979, 101, 5512-5515. [all data]

Meot-Ner (Mautner), 1988
Meot-Ner (Mautner), M., Models for Strong Interactions in Proteins and Enzymes. 2. Interactions of Ions with the Peptide Link and Imidazole, J. Am. Chem. Soc., 1988, 110, 10, 3075, https://doi.org/10.1021/ja00218a014 . [all data]

Meot-Ner (Mautner), Ross, et al., 1985
Meot-Ner (Mautner), M.; Ross, M.M.; Campana, J.E., Stable Hydrogen - Bonded Isomers of Covalent Ions, J. Am. Chem. Soc., 1985, 107, 4835. [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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