1H-Imidazole

• Formula: C₃H₄N₂
• Molecular weight: 68.0773
• IUPAC Standard InChI: InChI=1S/C3H4N2/c1-2-5-3-4-1/h1-3H,(H,4,5) Copy

  
• IUPAC Standard InChIKey: RAXXELZNTBOGNW-UHFFFAOYSA-N Copy
• CAS Registry Number: 288-32-4
• Chemical structure:
  This structure is also available as a 2d Mol file or as a computed 3d SD file
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• Other names: Imidazole; Glyoxalin; Glyoxaline; Imidazol; Imutex; Methanimidamide, N,N'-1,2-ethenediyl-; Miazole; 1,3-Diaza-2,4-cyclopentadiene; 1,3-Diazole; Formamidine, N,N'-vinylene-; Iminazole; IMD; Pyrro(b)monazole; USAF EK-4733; NSC 60522
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• Information on this page:
  • Ion clustering data
  • Mass spectrum (electron ionization)
  • Gas Chromatography
  • References
  • Notes
• Other data available:
  • Gas phase thermochemistry data
  • Condensed phase thermochemistry data
  • Phase change data
  • Reaction thermochemistry data
  • Gas phase ion energetics data
  • IR Spectrum
  • UV/Visible spectrum
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Ion clustering data

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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
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

 +  = ( • )

By formula: C₂H₃O₂^- + C₃H₄N₂ = (C₂H₃O₂^- • C₃H₄N₂)

 +  = ( • )

By formula: C₃H₃N₂^- + C₃H₄N₂ = (C₃H₃N₂^- • C₃H₄N₂)

C₃H₄N₂⁺ +  = (C₃H₄N₂⁺ • )

By formula: C₃H₄N₂⁺ + C₃H₄N₂ = (C₃H₄N₂⁺ • C₃H₄N₂)

C₄H₁₂N⁺ +  = (C₄H₁₂N⁺ • )

By formula: C₄H₁₂N⁺ + C₃H₄N₂ = (C₄H₁₂N⁺ • C₃H₄N₂)

 +  = ( • )

By formula: K⁺ + C₃H₄N₂ = (K⁺ • C₃H₄N₂)

 +  = ( • )

By formula: Li⁺ + C₃H₄N₂ = (Li⁺ • C₃H₄N₂)

 +  = ( • )

By formula: Na⁺ + C₃H₄N₂ = (Na⁺ • C₃H₄N₂)

Mass spectrum (electron ionization)

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

Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director

Spectrum

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Additional Data

Gas Chromatography

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

Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director

Kovats' RI, non-polar column, isothermal

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Kovats' RI, non-polar column, custom temperature program

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Kovats' RI, polar column, isothermal

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Van Den Dool and Kratz RI, non-polar column, temperature ramp

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Normal alkane RI, non-polar column, custom temperature program

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Normal alkane RI, polar column, temperature ramp

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References

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

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]

Huang and Rodgers, 2002
Huang, H.; Rodgers, M.T., Sigma versus Pi interactions in alkali metal ion binding to azoles: Threshold collision-induced dissociation and ab initio theory studies, J. Phys. Chem. A, 2002, 106, 16, 4277, https://doi.org/10.1021/jp013630b . [all data]

Armentrout and Rodgers, 2000
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 Alkali Metal Ion Binding Affinities of Several Azoles Determined by Threshold Collision-Induced Dissociation, Int. J. Mass Spectrom. Ion Proc., 1999, 185/186/187, 359. [all data]

Zhuravleva, 2000
Zhuravleva, I.L., Evaluation of the polarity and boiling points of nitrogen-containing heterocyclic compounds by gas chromatography, Russ. Chem. Bull. (Engl. Transl.), 2000, 49, 2, 325-328, https://doi.org/10.1007/BF02494682 . [all data]

Golovnya, Kuz'menko, et al., 1999
Golovnya, R.V.; Kuz'menko, T.E.; Zhuravleva, I.L., Gas chromatographic indicator of the ability of five- and six-membered heterocyclic nitrogen-containing compounds for self-association in pure liquids, Russ. Chem. Bull. (Engl. Transl.), 1999, 48, 4, 726-729, https://doi.org/10.1007/BF02496256 . [all data]

Golovnya, Zhuravleva, et al., 1992
Golovnya, R.V.; Zhuravleva, I.L.; Sal'kova, M.A., Prediction of Retention Indexes of Alkylimadazoles Under Conditions of Capillary Gas Chromatography, J. Anal. Chem. USSR (Engl. Transl.), 1992, 7, 932-937. [all data]

Ramsey, Lee, et al., 1980
Ramsey, J.D.; Lee, T.D.; Osselton, M.D.; Moffat, A.C., Gas-liquid chromatographic retention indices of 296 non-drug substances on SE-30 or OV-1 likely to be encountered in toxicological analyses, J. Chromatogr., 1980, 184, 2, 185-206, https://doi.org/10.1016/S0021-9673(00)85641-1 . [all data]

Peng, Ding, et al., 1988
Peng, C.T.; Ding, S.F.; Hua, R.L.; Yang, Z.C., Prediction of Retention Indexes I. Structure-Retention Index Relationship on Apolar Columns, J. Chromatogr., 1988, 436, 137-172, https://doi.org/10.1016/S0021-9673(00)94575-8 . [all data]

Ardrey and Moffat, 1981
Ardrey, R.E.; Moffat, A.C., Gas-liquid chromatographic retention indices of 1318 substances of toxicological interest on SE-30 or OV-1 stationary phase, J. Chromatogr., 1981, 220, 3, 195-252, https://doi.org/10.1016/S0021-9673(00)81925-1 . [all data]

Wong and Bernhard, 1988
Wong, J.M.; Bernhard, R.A., Effect of nitrogen source on pyrazine formation, J. Agric. Food Chem., 1988, 36, 1, 123-129, https://doi.org/10.1021/jf00079a032 . [all data]

Notes

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• Symbols used in this document:
  

  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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