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 151 to 200)
  • 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 101 to 150, 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:
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

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 151 to 200

C₁₀H₄Cl₂O₂^- +  = (C₁₀H₄Cl₂O₂^- • )

By formula: C₁₀H₄Cl₂O₂^- + CH₄O = (C₁₀H₄Cl₂O₂^- • CH₄O)

Free energy of reaction

CH₆N⁺ +  = (CH₆N⁺ • )

By formula: CH₆N⁺ + CH₄O = (CH₆N⁺ • CH₄O)

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

 +  =  + 2

By formula: C₇H₁₆O₃ + H₂O = C₅H₁₀O₂ + 2CH₄O

 +  = ( • )

By formula: C₁₀H₆O₂^- + CH₄O = (C₁₀H₆O₂^- • CH₄O)

Free energy of reaction

C₆H₄FNO₂^- +  = (C₆H₄FNO₂^- • )

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

Free energy of reaction

C₆H₄FNO₂^- +  = (C₆H₄FNO₂^- • )

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

Free energy of reaction

C₆H₄ClNO₂^- +  = (C₆H₄ClNO₂^- • )

By formula: C₆H₄ClNO₂^- + CH₄O = (C₆H₄ClNO₂^- • CH₄O)

Free energy of reaction

C₆H₄ClNO₂^- +  = (C₆H₄ClNO₂^- • )

By formula: C₆H₄ClNO₂^- + CH₄O = (C₆H₄ClNO₂^- • CH₄O)

Free energy of reaction

C₆H₄ClNO₂^- +  = (C₆H₄ClNO₂^- • )

By formula: C₆H₄ClNO₂^- + CH₄O = (C₆H₄ClNO₂^- • CH₄O)

Free energy of reaction

C₇H₇NO₂^- +  = (C₇H₇NO₂^- • )

By formula: C₇H₇NO₂^- + CH₄O = (C₇H₇NO₂^- • CH₄O)

Free energy of reaction

C₇H₇NO₂^- +  = (C₇H₇NO₂^- • )

By formula: C₇H₇NO₂^- + CH₄O = (C₇H₇NO₂^- • CH₄O)

Free energy of reaction

C₆H₄N₂O₄^- +  = (C₆H₄N₂O₄^- • )

By formula: C₆H₄N₂O₄^- + CH₄O = (C₆H₄N₂O₄^- • CH₄O)

Free energy of reaction

C₆H₄N₂O₄^- +  = (C₆H₄N₂O₄^- • )

By formula: C₆H₄N₂O₄^- + CH₄O = (C₆H₄N₂O₄^- • CH₄O)

Free energy of reaction

C₆H₄N₂O₄^- +  = (C₆H₄N₂O₄^- • )

By formula: C₆H₄N₂O₄^- + CH₄O = (C₆H₄N₂O₄^- • CH₄O)

Free energy of reaction

C₆F₄O₂^- +  = (C₆F₄O₂^- • )

By formula: C₆F₄O₂^- + CH₄O = (C₆F₄O₂^- • CH₄O)

Free energy of reaction

 +  = ( • )

By formula: C₆H₄O₂^- + CH₄O = (C₆H₄O₂^- • CH₄O)

Free energy of reaction

C₇H₄N₂O₂^- +  = (C₇H₄N₂O₂^- • )

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

Free energy of reaction

C₄H₂O₃^- +  = (C₄H₂O₃^- • )

By formula: C₄H₂O₃^- + CH₄O = (C₄H₂O₃^- • CH₄O)

Free energy of reaction

C₇H₄N₂O₂^- +  = (C₇H₄N₂O₂^- • )

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

Free energy of reaction

C₈H₉NO₂^- +  = (C₈H₉NO₂^- • )

By formula: C₈H₉NO₂^- + CH₄O = (C₈H₉NO₂^- • CH₄O)

Free energy of reaction

C₇H₇NO₃^- +  = (C₇H₇NO₃^- • )

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

Free energy of reaction

( •  • ) +  = ( • 2 • )

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

 +  =

By formula: C₅H₁₀ + CH₄O = C₆H₁₄O

( • 2 • ) +  = ( • 3 • )

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

( •  • ) +  = ( • 2 • )

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

( •  • ) +  = ( • 2 • )

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

(CH₃O^- • ) +  = (CH₃O^- •  • )

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

Free energy of reaction

(C₂H₄N⁺ •  • 2) +  = (C₂H₄N⁺ • 2 • 2)

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

 +  =  + 2

By formula: C₆H₁₄O₂ + H₂O = C₄H₈O + 2CH₄O

( • 2) +  = ( •  • 2)

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

( • 2) +  = ( •  • 2)

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

(C₂H₄N⁺ •  • ) +  = (C₂H₄N⁺ • 2 • )

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

C₂H₄NO₂^- +  = C₃H₈NO₃^-

By formula: C₂H₄NO₂^- + CH₄O = C₃H₈NO₃^-

( • ) +  = ( •  • )

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

( • ) +  = ( •  • )

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

( • ) +  = ( •  • )

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

HS^- +  = (HS^- • )

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

 +  = ( • )

By formula: C₅H₅^- + CH₄O = (C₅H₅^- • CH₄O)

 +  = C₇H₉OS^-

By formula: C₆H₅S^- + CH₄O = C₇H₉OS^-

( • 2) +  = ( • 3)

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

( • 3) +  = ( • 4)

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

(C₂H₄N⁺ • ) +  = (C₂H₄N⁺ •  • )

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

( • ) +  = ( • 2)

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

C₂H₇O₂^- +  +  = C₂H₉O₃^-

By formula: C₂H₇O₂^- + H₂O + CH₄O = C₂H₉O₃^-

C₃H₁₁O₃^- +  + 2 = C₃H₁₃O₄^-

By formula: C₃H₁₁O₃^- + H₂O + 2CH₄O = C₃H₁₃O₄^-

C₂H₉O₃^- + 2 +  = C₂H₁₁O₄^-

By formula: C₂H₉O₃^- + 2H₂O + CH₄O = C₂H₁₁O₄^-

 +  = ( • )

By formula: C₂H₃O₂^- + CH₄O = (C₂H₃O₂^- • CH₄O)

(C₃H₁₀N⁺ •  • ) +  = (C₃H₁₀N⁺ • 2 • )

By formula: (C₃H₁₀N⁺ • CH₄O • C₃H₉N) + CH₄O = (C₃H₁₀N⁺ • 2CH₄O • C₃H₉N)

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

(CH₃O^- • 2) +  = (CH₃O^- • 3)

By formula: (CH₃O^- • 2CH₄O) + CH₄O = (CH₃O^- • 3CH₄O)

(CH₃O^- • 3) +  = (CH₃O^- • 4)

By formula: (CH₃O^- • 3CH₄O) + CH₄O = (CH₃O^- • 4CH₄O)

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.

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]

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]

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]

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]

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]

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]

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]

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]

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]

Wiberg, Morgan, et al., 1994
Wiberg, K.B.; Morgan, K.M.; Maltz, H., Thermochemistry of carbonyl reactions. 6. A study of hydration equilibria, J. Am. Chem. Soc., 1994, 116, 11067-11077. [all data]

Wiberg and Squires, 1981
Wiberg, K.B.; Squires, R.R., Thermochemical studies of carbonyl reactions. 2. Steric effects in acetal and ketal hydrolysis, J. Am. Chem. Soc., 1981, 103, 4473-4478. [all data]

Nieckarz, Atkins, et al., 2008
Nieckarz, R.J.; Atkins, C.G.; McMahon, T.B., Effects of Isomerization on the Measured Thermochemical Properties of Deprotonated Glycine/Protic-Solvent Clusters, Chemphyschem, 2008, 9, 18, 2816-2825, https://doi.org/10.1002/cphc.200800525 . [all data]

Meot-ner, 1988
Meot-ner, M., Ionic Hydrogen Bond and Ion Solvation. ₆. Interaction Energies of the Acetate Ion with Organic Molecules. Comparison of CH₃COO^- with Cl^-, CN^-, and SH^-, J. Am. Chem. Soc., 1988, 110, 12, 3854, https://doi.org/10.1021/ja00220a022 . [all data]

Meot-ner, 1988, 2
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]

Sieck and Meot-ner, 1989
Sieck, L.W.; Meot-ner, M., Ionic Hydrogen Bond and Ion Solvation. 8. RS-..HOR Bond Strengths. Correlation with Acidities., J. Phys. Chem., 1989, 93, 4, 1586, https://doi.org/10.1021/j100341a079 . [all data]

Guo, Conklin, et al., 1989
Guo, B.C.; Conklin, B.J.; Castleman, A.W., Thermochemical Properties of Ion Complexes Na+(M)n in the Gas Phase, J. Am. Chem. Soc., 1989, 111, 17, 6506, https://doi.org/10.1021/ja00199a005 . [all data]

Guo and Castleman, 1990
Guo, B.C.; Castleman, A.W., The Association Reactions of Pb+ Ion with CH3OH and CH3NH2 in the Gas Phase, Int. J. Mass Spectrom. Ion Proc., 1990, 100, 665, https://doi.org/10.1016/0168-1176(90)85101-7 . [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]

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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