Methyl Alcohol

Formula: CH₄O
Molecular weight: 32.0419
IUPAC Standard InChI: InChI=1S/CH4O/c1-2/h2H,1H3
IUPAC Standard InChIKey: OKKJLVBELUTLKV-UHFFFAOYSA-N
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
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Isotopologues:
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
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Gas phase ion energetics data

Go To: Top, References, Notes

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

View reactions leading to CH₄O⁺ (ion structure unspecified)

Quantity	Value	Units	Method	Reference	Comment
IE (evaluated)	10.84 ± 0.01	eV	N/A	N/A	L
Quantity	Value	Units	Method	Reference	Comment
Proton affinity (review)	180.3	kcal/mol	N/A	Hunter and Lias, 1998	HL
Quantity	Value	Units	Method	Reference	Comment
Gas basicity	173.2	kcal/mol	N/A	Hunter and Lias, 1998	HL

Ionization energy determinations

IE (eV)	Method	Reference	Comment
10.85 ± 0.03	PI	Tao, Klemm, et al., 1992	LL
10.82 ± 0.05	EI	Holmes and Lossing, 1991	LL
10.84 ± 0.07	EI	Bowen and Maccoll, 1984	LBLHLM
10.9	EI	Mishchanchuk, Pokrovskii, et al., 1982	LBLHLM
10.84 ± 0.08	EI	Allam, Migahed, et al., 1982	LBLHLM
10.90 ± 0.03	EI	Sahini, Constantin, et al., 1978	LLK
10.85 ± 0.01	PI	Berkowitz, 1978	LLK
10.846 ± 0.002	PE	MacNeil and Dixon, 1977	LLK
10.90 ± 0.12	EI	Finney and Harrison, 1972	LLK
10.83 ± 0.03	PI	Warneck, 1971	LLK
10.85 ± 0.02	PE	Cocksey, Eland, et al., 1971	LLK
10.85	PE	Baker, Betteridge, et al., 1971	LLK
10.85	PE	Baker, Betteridge, et al., 1971	LLK
10.829 ± 0.015	PI	Omura, Kaneko, et al., 1969	RDSH
10.85	EI	Lifshitz, Shapiro, et al., 1969	RDSH
10.83	PE	Dewar and Worley, 1969	RDSH
10.84 ± 0.02	PI	Refaey and Chupka, 1968	RDSH
10.85	CI	Cermak, 1968	RDSH
10.83	PE	Al-Joboury and Turner, 1964	RDSH
10.85 ± 0.02	PI	Watanabe, 1954	RDSH
10.96	EI	Vorob'ev, Furlei, et al., 1989	Vertical value; LL
11.0	PE	Von Niessen, Bieri, et al., 1980	Vertical value; LLK
10.95	PE	Utsunomiya, Kobayashi, et al., 1980	Vertical value; LLK
10.95	PE	Kobayashi, 1978	Vertical value; LLK
10.86	PE	Benoit and Harrison, 1977	Vertical value; LLK
10.97 ± 0.03	PE	Peel and Willett, 1975	Vertical value; LLK
10.96	PE	Robin and Kuebler, 1973	Vertical value; LLK
10.95	PE	Ogata, Onizuka, et al., 1973	Vertical value; LLK
10.94	PE	Katsumata, Iwai, et al., 1973	Vertical value; LLK
10.95	PE	Ogata, Onizuka, et al., 1972	Vertical value; LLK
10.96	PE	Baker, Betteridge, et al., 1971	Vertical value; LLK

Appearance energy determinations

Ion	AE (eV)	Other Products	Method	Reference	Comment
CH⁺	22.31 ± 0.09	?	EI	Reed and Snedden, 1956	RDSH
CHO⁺	13.06 ± 0.10	H₂+H	PI	Warneck, 1971	LLK
CHO⁺	14.0 ± 0.2	H₂+H	EI	Lifshitz, Shapiro, et al., 1969	RDSH
CH₂⁺	14.05 ± 0.05	H₂O	PI	Warneck, 1971	LLK
CH₂⁺	15.3	H₂O	EI	Haney and Franklin, 1968	RDSH
CH₂O⁺	10.9	H₂	EI	Mishchanchuk, Pokrovskii, et al., 1982	LBLHLM
CH₂O⁺	12.05 ± 0.12	H₂	PI	Warneck, 1971	LLK
CH₂O⁺	12.45	H₂	PI	Refaey and Chupka, 1968	RDSH
CH₃⁺	13.82 ± 0.04	OH	PI	Warneck, 1971	LLK
CH₃⁺	13.5	OH	EI	Friedman, Long, et al., 1957	RDSH
CH₃O⁺	11.67 ± 0.09	H	EI	Bowen and Maccoll, 1984	LBLHLM
CH₃O⁺	10.4	H	EI	Mishchanchuk, Pokrovskii, et al., 1982	LBLHLM
CH₃O⁺	11.85 ± 0.08	H	EI	Allam, Migahed, et al., 1982	LBLHLM
CH₃O⁺	11.88 ± 0.05	H	EI	Selim and Helal, 1981	LLK
CH₃O⁺	11.69	H	EI	Lossing, 1977	LLK
CH₃O⁺	11.76 ± 0.11	H	EI	Finney and Harrison, 1972	LLK
CH₃O⁺	11.55 ± 0.03	H	PI	Warneck, 1971	LLK
CH₃O⁺	11.66 ± 0.04	H	PI	Omura, Kaneko, et al., 1969	RDSH
CH₃O⁺	11.67	H	EI	Lifshitz, Shapiro, et al., 1969	RDSH
CH₃O⁺	11.67 ± 0.03	H	PI	Refaey and Chupka, 1968	RDSH
CH₃O⁺[CH₂OH⁺]	11.649 ± 0.003	H	PI	Berkowitz, Ellison, et al., 1994	Unpublished results of B. Ruscic and J. Berkowitz; LL
CO⁺	13.7	2H₂	EI	Friedman, Long, et al., 1957	RDSH
CO⁺	14.31 ± 0.05	2H₂	EI	Friedland and Strakna, 1956	RDSH

De-protonation reactions

CH₃O^- + = Methyl Alcohol

By formula: CH₃O^- + H⁺ = CH₄O

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	382. ± 2.	kcal/mol	AVG	N/A	Average of 6 values; Individual data points
Quantity	Value	Units	Method	Reference	Comment
Δ_rG°	376.02 ± 0.62	kcal/mol	H-TS	Nee, Osterwalder, et al., 2006	gas phase; B
Δ_rG°	376.04 ± 0.55	kcal/mol	H-TS	Osborn, Leahy, et al., 1998	gas phase; B
Δ_rG°	374.0 ± 2.0	kcal/mol	IMRE	Bartmess, Scott, et al., 1979	gas phase; The acidity is 1.2 kcal/mol stronger than that from the D-EA cycle, due to the multi-compound fit for the acidity scale.; value altered from reference due to change in acidity scale; B
Δ_rG°	374.6 ± 2.1	kcal/mol	H-TS	Haas and Harrison, 1993	gas phase; Both metastable and 50 eV collision energy.; B
Δ_rG°	375.10 ± 0.60	kcal/mol	TDEq	Meot-ner and Sieck, 1986	gas phase; Experimental entropy: 21.5 eu, 0.6 less than H2O; B

References

Go To: Top, Gas phase ion energetics data, Notes

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]

Tao, Klemm, et al., 1992
Tao, W.; Klemm, R.B.; Nesbitt, F.L.; Stief, J.L., A discharge flow-photoionization mass spectrometric study of hydroxymethyl radicals (H₂COH and H₂COD): Photoionization spectrum and ionization energy, J. Phys. Chem., 1992, 96, 104. [all data]

Holmes and Lossing, 1991
Holmes, J.L.; Lossing, F.P., Ionization energies of homologous organic compounds and correlation with molecular size, Org. Mass Spectrom., 1991, 26, 537. [all data]

Bowen and Maccoll, 1984
Bowen, R.D.; Maccoll, A., Low energy, low temperature mass spectra, Org. Mass Spectrom., 1984, 19, 379. [all data]

Mishchanchuk, Pokrovskii, et al., 1982
Mishchanchuk, B.G.; Pokrovskii, V.A.; Shabel'nikov, V.P.; Korol, E.N., Mass spectrometric study of energy characteristics of methanol and ethanol ions during ionization by a strong electric field, Teor. Eksp. Khim., 1982, 18, 307. [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]

Sahini, Constantin, et al., 1978
Sahini, V.E.; Constantin, V.; Serban, I., Determination of ionization potentials using a MI-1305 mass spectrometer, Rev. Roum. Chim., 1978, 23, 479. [all data]

Berkowitz, 1978
Berkowitz, J., Photoionization of CH₃OH, CD₃OH, and CH₃OD: Dissociative ionization mechanisms and ionic structures, J. Chem. Phys., 1978, 69, 3044. [all data]

MacNeil and Dixon, 1977
MacNeil, K.A.G.; Dixon, R.N., High-resolution photoelectron spectroscopy of methanol and its deuterated derivatives: Internal rotation in the ground ionic state, J. Electron Spectrosc. Relat. Phenom., 1977, 11, 315. [all data]

Finney and Harrison, 1972
Finney, C.D.; Harrison, A.G., A third-derivative method for determining electron-impact onset potentials, Int. J. Mass Spectrom. Ion Phys., 1972, 9, 221. [all data]

Warneck, 1971
Warneck, P., Photoionisation von methanol und formaldehyd, Z. Naturforsch. A:, 1971, 26, 2047. [all data]

Cocksey, Eland, et al., 1971
Cocksey, B.J.; Eland, J.H.D.; Danby, C.J., The effect of alkyl substitution on ionisation potential, J. Chem. Soc., 1971, (B), 790. [all data]

Baker, Betteridge, et al., 1971
Baker, A.D.; Betteridge, D.; Kemp, N.R.; Kirby, R.E., Application of photoelectron spectrometry to pesticide analysis. II.Photoelectron spectra of hydroxy-, and halo-alkanes and halohydrins, Anal. Chem., 1971, 43, 375. [all data]

Omura, Kaneko, et al., 1969
Omura, I.; Kaneko, T.; Yamada, Y.; Tanaka, K., Mass spectrometric studies of photoionization. V. Methanol and methanol-d, J. Phys. Soc. Japan, 1969, 27, 981. [all data]

Lifshitz, Shapiro, et al., 1969
Lifshitz, C.; Shapiro, M.; Sternberg, R., Isotopic effects on metastable transitions. IV. Isotopic methanols, Israel J. Chem., 1969, 7, 391. [all data]

Dewar and Worley, 1969
Dewar, M.J.S.; Worley, S.D., Photoelectron spectra of molecules. I. Ionization potentials of some organic molecules and their interpretation, J. Chem. Phys., 1969, 50, 654. [all data]

Refaey and Chupka, 1968
Refaey, K.M.A.; Chupka, W.A., Photoionization of the lower aliphatic alcohols with mass analysis, J. Chem. Phys., 1968, 48, 5205. [all data]

Cermak, 1968
Cermak, V., Penning ionization electron spectroscopy. I. Determination of ionization potentials of polyatomic molecules, Collection Czech. Chem. Commun., 1968, 33, 2739. [all data]

Al-Joboury and Turner, 1964
Al-Joboury, M.I.; Turner, D.W., Molecular photoelectron spectroscopy. Part II. A summary of ionization potentials, J. Chem. Soc., 1964, 4434. [all data]

Watanabe, 1954
Watanabe, K., Photoionization and total absorption cross section of gases. I. Ionization potentials of several molecules. Cross sections of NH₃ and NO, J. Chem. Phys., 1954, 22, 1564. [all data]

Vorob'ev, Furlei, et al., 1989
Vorob'ev, A.S.; Furlei, I.I.; Sultanov, A.S.; Khvostenko, V.I.; Leplyanin, G.V.; Derzhinskii, A.R.; Tolstikov, G.A., Mass spectrometry of reasonance capture of electrons and photoelectron spectroscopy of molecules of ethylene oxide, ethylene sulfide, and their derivatives, Bull. Acad. Sci. USSR, Div. Chem. Sci., 1989, 1388. [all data]

Von Niessen, Bieri, et al., 1980
Von Niessen, W.; Bieri, G.; Asbrink, L., 30.4 nm He(II) photoelectron spectra of organic molecules. Part III. Oxo-compounds (C,H,O), J. Electron Spectrosc. Relat. Phenom., 1980, 21, 175. [all data]

Utsunomiya, Kobayashi, et al., 1980
Utsunomiya, C.; Kobayashi, T.; Nagakura, S., Photoelectron angular distribution measurements for some aliphatic alcohols, amines, halides, Bull. Chem. Soc. Jpn., 1980, 53, 1216. [all data]

Kobayashi, 1978
Kobayashi, T., A simple general tendency in photoelectron angular distributions of some monosubstituted benzenes, Phys. Lett., 1978, 69, 105. [all data]

Benoit and Harrison, 1977
Benoit, F.M.; Harrison, A.G., Predictive value of proton affinity. Ionization energy correlations involving oxygenated molecules, J. Am. Chem. Soc., 1977, 99, 3980. [all data]

Peel and Willett, 1975
Peel, J.B.; Willett, G.D., Photoelectron spectroscopic studies of the higher alcohols, Aust. J. Chem., 1975, 28, 2357. [all data]

Robin and Kuebler, 1973
Robin, M.B.; Kuebler, N.A., Excited electronic states of the simple alcohols, J. Electron Spectrosc. Relat. Phenom., 1973, 1, 13. [all data]

Ogata, Onizuka, et al., 1973
Ogata, H.; Onizuka, H.; Nihei, Y.; Kamada, H., The photoelectron spectra of alcohols, mercaptans and amines, Bull. Chem. Soc. Jpn., 1973, 46, 3036. [all data]

Katsumata, Iwai, et al., 1973
Katsumata, S.; Iwai, T.; Kimura, K., Photoelectron spectra and sum rule consideration. Higher alkyl amines and alcohols, Bull. Chem. Soc. Jpn., 1973, 46, 3391. [all data]

Ogata, Onizuka, et al., 1972
Ogata, H.; Onizuka, H.; Nihei, Y.; Kamada, H., On the first bands of the photoelectron spectra of amines, alcohols, and mercaptans, Chem. Lett., 1972, 895. [all data]

Reed and Snedden, 1956
Reed, R.I.; Snedden, W., Studies in electron impact methods. Part 6.-The formation of the methine and carbon ions, J. Chem. Soc. Faraday Trans., 1956, 55, 876. [all data]

Haney and Franklin, 1968
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]

Friedman, Long, et al., 1957
Friedman, L.; Long, F.A.; Wolfsberg, M., Study of the mass spectra of the lower aliphatic alcohols, J. Chem. Phys., 1957, 27, 613. [all data]

Selim and Helal, 1981
Selim, E.T.M.; Helal, A.I., Heat of formation of CH₂=OH⁺ fragment ion, Indian J. Pure Appl. Phys., 1981, 19, 977. [all data]

Lossing, 1977
Lossing, F.P., Heats of formation of some isomeric [C_nH_2n+1]⁺ ions. Substitutional effects on ion stability, J. Am. Chem. Soc., 1977, 99, 7526. [all data]

Berkowitz, Ellison, et al., 1994
Berkowitz, J.; Ellison, G.B.; Gutman, D., Three methods to measure RH bond energies, J. Phys. Chem., 1994, 98, 2744. [all data]

Friedland and Strakna, 1956
Friedland, S.S.; Strakna, R.E., Appearance potential studies. I, J. Phys. Chem., 1956, 60, 815. [all data]

Nee, Osterwalder, et al., 2006
Nee, M.J.; Osterwalder, A.; Zhou, J.; Neumark, D.M., Slow electron velocity-map imaging photoelectron spectra of the methoxide anion, J. Chem. Phys., 2006, 125, 1, 014306, https://doi.org/10.1063/1.2212411 . [all data]

Osborn, Leahy, et al., 1998
Osborn, D.L.; Leahy, D.J.; Kim, E.H.; deBeer, E.; Neumark, D.M., Photoelectron spectroscopy of CH3O- and CD3O-, Chem. Phys. Lett., 1998, 292, 4-6, 651-655, https://doi.org/10.1016/S0009-2614(98)00717-9 . [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]

Haas and Harrison, 1993
Haas, M.J.; Harrison, A.G., The Fragmentation of Proton-Bound Cluster Ions and the Gas-Phase Acidities of Alcohols, Int. J. Mass Spectrom. Ion Proc., 1993, 124, 2, 115, https://doi.org/10.1016/0168-1176(93)80003-W . [all data]

Meot-ner and Sieck, 1986
Meot-ner, M.; Sieck, L.W., Relative acidities of water and methanol, and the stabilities of the dimer adducts, J. Phys. Chem., 1986, 90, 6687. [all data]

Notes

Go To: Top, Gas phase ion energetics data, References

Symbols used in this document:

AE Appearance energy

IE (evaluated) Recommended ionization energy

Δ_rG° Free energy of reaction at standard conditions

Δ_rH° Enthalpy of reaction at standard conditions
Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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AE	Appearance energy
IE (evaluated)	Recommended ionization energy
Δ_rG°	Free energy of reaction at standard conditions
Δ_rH°	Enthalpy of reaction at standard conditions