Ethanol

• Formula: C₂H₆O
• Molecular weight: 46.0684
• IUPAC Standard InChI: InChI=1S/C2H6O/c1-2-3/h3H,2H2,1H3 Copy

  
• IUPAC Standard InChIKey: LFQSCWFLJHTTHZ-UHFFFAOYSA-N Copy
• CAS Registry Number: 64-17-5
• 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.
• Isotopologues:
  • [2H6]ethanol
  • Ethanol-d1
  • C2H3D3O
  • Ethanol-d5
  • Ethanol-1,1-d2
• Other names: Ethyl alcohol; Alcohol; Alcohol anhydrous; Algrain; Anhydrol; Denatured ethanol; Ethyl hydrate; Ethyl hydroxide; Jaysol; Jaysol S; Methylcarbinol; SD Alchol 23-hydrogen; Tecsol; C2H5OH; Absolute ethanol; Cologne spirit; Fermentation alcohol; Grain alcohol; Molasses alcohol; Potato alcohol; Aethanol; Aethylalkohol; Alcohol, dehydrated; Alcool ethylique; Alcool etilico; Alkohol; Cologne spirits; Denatured alcohol CD-10; Denatured alcohol CD-5; Denatured alcohol CD-5a; Denatured alcohol SD-1; Denatured alcohol SD-13a; Denatured alcohol SD-17; Denatured alcohol SD-23a; Denatured alcohol SD-28; Denatured alcohol SD-3a; Denatured alcohol SD-30; Denatured alcohol SD-39b; Denatured alcohol SD-39c; Denatured alcohol SD-40m; Etanolo; Ethanol 200 proof; Ethyl alc; Etylowy alkohol; EtOH; NCI-C03134; Spirits of wine; Spirt; Alkoholu etylowego; Ethyl alcohol anhydrous; SD alcohol 23-hydrogen; UN 1170; Tecsol C; Alcare Hand Degermer; Absolute alcohol; Denatured alcohol; Ethanol, silent spirit; Ethylol; Punctilious ethyl alcohol; SD 3A
• Permanent link for this species. Use this link for bookmarking this species for future reference.
• Information on this page:
  • Ion clustering data
  • 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 77
  • Henry's Law data
  • Gas phase ion energetics data
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • Gas Chromatography
• Data at other public NIST sites:
  • Gas Phase Kinetics Database
  • X-ray Photoelectron Spectroscopy Database, version 5.0
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Ion clustering 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
RCD - Robert C. Dunbar

Note: Please consider using the reaction search for this species. This page allows searching of all reactions involving this species. Searches may be limited to ion clustering reactions. A general reaction search form is also available.

Clustering reactions

 +  = C₂H₆BrO^-

By formula: Br^- + C₂H₆O = C₂H₆BrO^-

 + 2 = C₄H₁₂BrO₂^-

By formula: Br^- + 2C₂H₆O = C₄H₁₂BrO₂^-

 + 3 = C₆H₁₈BrO₃^-

By formula: Br^- + 3C₂H₆O = C₆H₁₈BrO₃^-

CH₆N⁺ +  = (CH₆N⁺ • )

By formula: CH₆N⁺ + C₂H₆O = (CH₆N⁺ • C₂H₆O)

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

Free energy of reaction

CN^- +  = (CN^- • )

By formula: CN^- + C₂H₆O = (CN^- • C₂H₆O)

 +  = ( • )

By formula: C₂H₃O₂^- + C₂H₆O = (C₂H₃O₂^- • C₂H₆O)

C₂H₄NO₂^- +  = C₄H₁₀NO₃^-

By formula: C₂H₄NO₂^- + C₂H₆O = C₄H₁₀NO₃^-

C₂H₅O⁺ +  = (C₂H₅O⁺ • )

By formula: C₂H₅O⁺ + C₂H₆O = (C₂H₅O⁺ • C₂H₆O)

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

C₂H₅O^- +  = (C₂H₅O^- • )

By formula: C₂H₅O^- + C₂H₆O = (C₂H₅O^- • C₂H₆O)

C₂H₆FO^- + 2 = C₄H₁₂FO₂^-

By formula: C₂H₆FO^- + 2C₂H₆O = C₄H₁₂FO₂^-

C₂H₇O⁺ +  = (C₂H₇O⁺ • )

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

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

C₃H₇O^- +  = (C₃H₇O^- • )

By formula: C₃H₇O^- + C₂H₆O = (C₃H₇O^- • C₂H₆O)

C₃H₉O⁺ +  = (C₃H₉O⁺ • )

By formula: C₃H₉O⁺ + C₂H₆O = (C₃H₉O⁺ • C₂H₆O)

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

C₃H₉O⁺ +  = (C₃H₉O⁺ • )

By formula: C₃H₉O⁺ + C₂H₆O = (C₃H₉O⁺ • C₂H₆O)

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

C₃H₉Si⁺ +  = (C₃H₉Si⁺ • )

By formula: C₃H₉Si⁺ + C₂H₆O = (C₃H₉Si⁺ • C₂H₆O)

Free energy of reaction

C₃H₉Sn⁺ +  = (C₃H₉Sn⁺ • )

By formula: C₃H₉Sn⁺ + C₂H₆O = (C₃H₉Sn⁺ • C₂H₆O)

Free energy of reaction

C₄H₉O^- +  = (C₄H₉O^- • )

By formula: C₄H₉O^- + C₂H₆O = (C₄H₉O^- • C₂H₆O)

C₄H₁₂FO₂^- + 3 = C₆H₁₈FO₃^-

By formula: C₄H₁₂FO₂^- + 3C₂H₆O = C₆H₁₈FO₃^-

C₅H₁₁O^- +  = (C₅H₁₁O^- • )

By formula: C₅H₁₁O^- + C₂H₆O = (C₅H₁₁O^- • C₂H₆O)

 +  = ( • )

By formula: C₆H₅O^- + C₂H₆O = (C₆H₅O^- • C₂H₆O)

 +  = C₈H₁₁O₂^-

By formula: C₆H₅O^- + C₂H₆O = C₈H₁₁O₂^-

 +  = ( • )

By formula: Cl^- + C₂H₆O = (Cl^- • C₂H₆O)

Free energy of reaction

( • ) +  = ( • 2)

By formula: (Cl^- • C₂H₆O) + C₂H₆O = (Cl^- • 2C₂H₆O)

( • 2) +  = ( • 3)

By formula: (Cl^- • 2C₂H₆O) + C₂H₆O = (Cl^- • 3C₂H₆O)

( • 3) +  = ( • 4)

By formula: (Cl^- • 3C₂H₆O) + C₂H₆O = (Cl^- • 4C₂H₆O)

( • 4) +  = ( • 5)

By formula: (Cl^- • 4C₂H₆O) + C₂H₆O = (Cl^- • 5C₂H₆O)

( • 5) +  = ( • 6)

By formula: (Cl^- • 5C₂H₆O) + C₂H₆O = (Cl^- • 6C₂H₆O)

( • 6) +  = ( • 7)

By formula: (Cl^- • 6C₂H₆O) + C₂H₆O = (Cl^- • 7C₂H₆O)

( • 7) +  = ( • 8)

By formula: (Cl^- • 7C₂H₆O) + C₂H₆O = (Cl^- • 8C₂H₆O)

( • 8) +  = ( • 9)

By formula: (Cl^- • 8C₂H₆O) + C₂H₆O = (Cl^- • 9C₂H₆O)

( • 9) +  = ( • 10)

By formula: (Cl^- • 9C₂H₆O) + C₂H₆O = (Cl^- • 10C₂H₆O)

 +  = C₂H₅D₆FO^-

By formula: F^- + C₂H₆O = C₂H₅D₆FO^-

 +  = ( • )

By formula: F^- + C₂H₆O = (F^- • C₂H₆O)

HS^- +  = (HS^- • )

By formula: HS^- + C₂H₆O = (HS^- • C₂H₆O)

 +  = ( • )

By formula: I^- + C₂H₆O = (I^- • C₂H₆O)

 + 2 = C₄H₁₂IO₂^-

By formula: I^- + 2C₂H₆O = C₄H₁₂IO₂^-

 + 3 = C₆H₁₈IO₃^-

By formula: I^- + 3C₂H₆O = C₆H₁₈IO₃^-

 +  = ( • )

By formula: Li⁺ + C₂H₆O = (Li⁺ • C₂H₆O)

 +  = ( • )

By formula: Mg⁺ + C₂H₆O = (Mg⁺ • C₂H₆O)

 +  = ( • )

By formula: Na⁺ + C₂H₆O = (Na⁺ • C₂H₆O)

Free energy of reaction

( • ) +  = ( • 2)

By formula: (Na⁺ • C₂H₆O) + C₂H₆O = (Na⁺ • 2C₂H₆O)

References

Go To: Top, Ion clustering data, Notes

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

Bogdanov, Peschke, et al., 1999
Bogdanov, B.; Peschke, M.; Tonner, D.S.; Szulejko, J.E.; McMahon, T.B., Stepwise solvation of halides by alcohol molecules in the gas phase, Int. J. Mass Spectrom., 1999, 187, 707-725, https://doi.org/10.1016/S1387-3806(98)14180-5 . [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]

Hiraoka, Mizure, et al., 1988
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]

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]

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]

Larson and McMahon, 1987
Larson, J.W.; McMahon, T.B., Hydrogen bonding in gas phase anions. The energetics of interaction between cyanide ion and bronsted acids, J. Am. Chem. Soc., 1987, 109, 6230. [all data]

Payzant, Yamdagni, et al., 1971
Payzant, J.D.; Yamdagni, R.; Kebarle, P., Hydration of CN-, NO₂-, NO₃-, and HO- in the gas phase, Can. J. Chem., 1971, 49, 3308. [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]

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]

Larson and McMahon, 1982
Larson, J.W.; McMahon, T.B., Formation, Thermochemistry, and Relative Stabilities of Proton - Bound dimers of Oxygen n - Donor Bases from Ion Cyclotron Resonance Solvent - Exchange Equilibria Measurements, J. Am. Chem. Soc., 1982, 104, 23, 6255, https://doi.org/10.1021/ja00387a016 . [all data]

Grimsrud and Kebarle, 1973
Grimsrud, E.P.; Kebarle, P., Gas Phase Ion Equilibria Studies of the Solvation of the Hydrogen Ion by Methanol, Dimethyl Ether and Water. Effect of Hydrogen Bonding, J. Am. Chem. Soc., 1973, 95, 24, 7939, https://doi.org/10.1021/ja00805a002 . [all data]

Lias, Liebman, et al., 1984
Lias, S.G.; Liebman, J.F.; Levin, R.D., Evaluated gas phase basicities and proton affinities of molecules heats of formation of protonated molecules, J. Phys. Chem. Ref. Data, 1984, 13, 695. [all data]

Keesee and Castleman, 1986
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Caldwell, Rozeboom, et al., 1984
Caldwell, G.; Rozeboom, M.D.; Kiplinger, J.P.; Bartmess, J.E., Anion-alcohol hydrogen bond strengths in the gas phase, J. Am. Chem. Soc., 1984, 106, 4660. [all data]

Paul and Kebarle, 1990
Paul, G.J.C.; Kebarle, P., Thermodynamics of the Association Reactions OH- - H2O = HOHOH- and CH3O- - CH3OH = CH3OHOCH3- in the Gas Phase, J. Phys. Chem., 1990, 94, 12, 5184, https://doi.org/10.1021/j100375a076 . [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]

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]

McIver, Scott, et al., 1973
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Meot-Ner (Mautner), 1992
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Bomse and Beauchamp, 1981
Bomse, D.S.; Beauchamp, J.L., Slow Multiphoton Excitation as a Probe of Bimolecular and Unimolecular Reaction Energetics. Multiphoton Dissociation of Proton-Bound Alcohol Dimers, J. Am. Chem. Soc., 1981, 103, 12, 3292, https://doi.org/10.1021/ja00402a011 . [all data]

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Stone and Splinter, 1984
Stone, J.A.; Splinter, D.E., A high-pressure mass spectrometric study of the binding of (CH₃)₃Sn⁺ to lewis bases in the gas phase, Int. J. Mass Spectrom. Ion Processes, 1984, 59, 169. [all data]

Hiraoka, 1987
Hiraoka, K., Relation Between Gas Phase Stepwise and Bulk Solvation of Cl^- with Water and Aliphatic Alcohols, Bull. Chem. Soc. Japan, 1987, 60, 7, 2555, https://doi.org/10.1246/bcsj.60.2555 . [all data]

Larson and McMahon, 1984
Larson, J.W.; McMahon, T.B., Hydrogen bonding in gas phase anions. An experimental investigation of the interaction between chloride ion and bronsted acids from ICR chloride exchange equilibria, J. Am. Chem. Soc., 1984, 106, 517. [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]

Larson and McMahon, 1984, 2
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Riveros, 1974
Riveros, J.M., Formation and Relative Stability of Negative Clustered Ions by Ion Cyclotron Resonance Spectroscopy, Adv. Mass Spectrom., 1974, 6, 277. [all data]

Riveros, Breda, et al., 1973
Riveros, J.M.; Breda, A.C.; Blair, L.K., Formation and relative stability of chloride ion clusters in the gas phase by ICR spectroscopy, J. Am. Chem. Soc., 1973, 95, 4066. [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]

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Larson, J.W.; McMahon, T.B., Strong hydrogen bonding in gas-phase anions. An ion cyclotron resonance determination of fluoride binding energetics to bronsted acids from gas-phase fluoride exchange equilibria measurements, J. Am. Chem. Soc., 1983, 105, 2944. [all data]

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DeTuri, V.F.; Ervin, K.M., Competitive threshold collision-induced dissociation: Gas-phase acidities and bond dissociation energies for a series of alcohols, J. Phys. Chem. A, 1999, 103, 35, 6911-6920, https://doi.org/10.1021/jp991459m . [all data]

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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]

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Operti, L.; Tews, E.C.; Freiser, B.S., Determination of Gas-Phase Ligand Binding Energies to Mg+ by FTMS Techniques, J. Am. Chem. Soc., 1988, 110, 12, 3847, https://doi.org/10.1021/ja00220a020 . [all data]

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Armentrout, P.B.; Rodgers, M.T., An Absolute Sodium Cation Affinity Scale: Threshold Collision-Induced Dissociation Experiments and ab Initio Theory, J. Phys. Chem A, 2000, 104, 11, 2238, https://doi.org/10.1021/jp991716n . [all data]

Rodgers and Armentrout, 1999
Rodgers, M.T.; Armentrout, P.B., Absolute Binding Energies of Sodium Ions to Short-Chain Alcohols, CnH2n+2O, n=1-4, Determined by Threshold Collision-Induced Dissociation Experiments and Ab Initio Theory, 1999, 4955. [all data]

McMahon and Ohanessian, 2000
McMahon, T.B.; Ohanessian, G., An Experimental and Ab Initio Study of the Nature of the Binding in Gas-Phase Complexes of Sodium Ions, Chem. Eur. J., 2000, 6, 16, 2931, https://doi.org/10.1002/1521-3765(20000818)6:16<2931::AID-CHEM2931>3.0.CO;2-7 . [all data]

Notes

Go To: Top, Ion clustering 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

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