1,3-Diazine

• Formula: C₄H₄N₂
• Molecular weight: 80.0880
• IUPAC Standard InChI: InChI=1S/C4H4N2/c1-2-5-4-6-3-1/h1-4H Copy

  
• IUPAC Standard InChIKey: CZPWVGJYEJSRLH-UHFFFAOYSA-N Copy
• CAS Registry Number: 289-95-2
• 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.
• Other names: Pyrimidine; m-Diazine; Metadiazine; Miazine; 1,3-Diazabenzene; Py; Pyr
• Permanent link for this species. Use this link for bookmarking this species for future reference.
• Information on this page:
  • Gas phase thermochemistry data
  • Condensed phase thermochemistry data
  • Phase change data
  • Reaction thermochemistry data
  • Gas phase ion energetics data
  • Ion clustering data
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • UV/Visible spectrum
  • Gas Chromatography
  • References
  • Notes
• Options:
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• NIST / TRC Web Thermo Tables, professional edition (thermophysical and thermochemical data)

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Gas phase thermochemistry 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 by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Condensed phase thermochemistry 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 by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Phase change 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:
BS - Robert L. Brown and Stephen E. Stein
AC - William E. Acree, Jr., James S. Chickos
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DRB - Donald R. Burgess, Jr.

Reaction thermochemistry 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:
MS - José A. Martinho Simões
B - John E. Bartmess
RCD - Robert C. Dunbar

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.

Individual Reactions

C₁₀H₅CrNO₅ (solution) +  (solution) =  (solution) +  (solution)

By formula: C₁₀H₅CrNO₅ (solution) + CO (solution) = C₆CrO₆ (solution) + C₄H₄N₂ (solution)

 (cr) +  (l) = C₁₀H₅NO₅W (cr) +  (g)

By formula: C₆O₆W (cr) + C₄H₄N₂ (l) = C₁₀H₅NO₅W (cr) + CO (g)

C₄H₃N₂^- +  =

By formula: C₄H₃N₂^- + H⁺ = C₄H₄N₂

 (solution) +  (solution) = C₁₀H₅NO₅W (solution) +  (solution)

By formula: C₆O₆W (solution) + C₄H₄N₂ (solution) = C₁₀H₅NO₅W (solution) + CO (solution)

C₃₉H₆₈O₃P₂W (solution) +  (solution) = C₄₄H₇₁NO₃P₂W (solution) +  (g)

By formula: C₃₉H₆₈O₃P₂W (solution) + C₄H₄N₂ (solution) = C₄₄H₇₁NO₃P₂W (solution) + H₂ (g)

C₁₄H₁₀CrN₂O₄ (cr) = 2 (g) + 4 (g) +  (cr)

By formula: C₁₄H₁₀CrN₂O₄ (cr) = 2C₄H₄N₂ (g) + 4CO (g) + Cr (cr)

C₈H₆MoO₃ (solution) + 3 (solution) = C₁₈H₁₅MoN₃O₃ (solution) +  (solution)

By formula: C₈H₆MoO₃ (solution) + 3C₄H₄N₂ (solution) = C₁₈H₁₅MoN₃O₃ (solution) + C₅H₆ (solution)

 +  = C₄H₄N₃O^-

By formula: NO^- + C₄H₄N₂ = C₄H₄N₃O^-

C₉H₉CrN₃O₃ (solution) + 3 (solution) = C₁₈H₁₅CrN₃O₃ (solution) + 3 (solution)

By formula: C₉H₉CrN₃O₃ (solution) + 3C₄H₄N₂ (solution) = C₁₈H₁₅CrN₃O₃ (solution) + 3C₂H₃N (solution)

C₇H₉Cl₂NPd (solution) +  (l) = (PdCl₂(C₅H₅N)₂) (solution) +  (solution)

By formula: C₇H₉Cl₂NPd (solution) + C₄H₄N₂ (l) = (PdCl₂(C₅H₅N)₂) (solution) + C₂H₄ (solution)

C₁₀H₅NO₅W (cr) +  (g) =  (g) +  (g)

By formula: C₁₀H₅NO₅W (cr) + CO (g) = C₆O₆W (g) + C₄H₄N₂ (g)

C₁₂H₁₆CrO₅ (solution) +  (solution) =  (solution) + C₁₀H₅CrNO₅ (solution)

By formula: C₁₂H₁₆CrO₅ (solution) + C₄H₄N₂ (solution) = C₇H₁₆ (solution) + C₁₀H₅CrNO₅ (solution)

C₃₉H₆₆MoO₃P₃ (solution) +  (solution) = C₄₄H₇₁MoNO₃P₂ (solution)

By formula: C₃₉H₆₆MoO₃P₃ (solution) + C₄H₄N₂ (solution) = C₄₄H₇₁MoNO₃P₂ (solution)

 (cr) + 3 (g) = C₁₈H₁₅MoN₃O₃ (cr) + 3 (g)

By formula: C₆MoO₆ (cr) + 3C₄H₄N₂ (g) = C₁₈H₁₅MoN₃O₃ (cr) + 3CO (g)

 (cr) + 3 (g) = C₁₈H₁₅N₃O₃W (g) + 3 (g)

By formula: C₆O₆W (cr) + 3C₄H₄N₂ (g) = C₁₈H₁₅N₃O₃W (g) + 3CO (g)

C₁₀H₅CrNO₅ (cr) +  (g) =  (g) +  (g)

By formula: C₁₀H₅CrNO₅ (cr) + CO (g) = C₆CrO₆ (g) + C₄H₄N₂ (g)

C₁₀H₅MoNO₅ (cr) +  (g) =  (g) +  (g)

By formula: C₁₀H₅MoNO₅ (cr) + CO (g) = C₆MoO₆ (g) + C₄H₄N₂ (g)

 +  = ( • )

By formula: Fe⁺ + C₄H₄N₂ = (Fe⁺ • C₄H₄N₂)

 +  = ( • )

By formula: Cr⁺ + C₄H₄N₂ = (Cr⁺ • C₄H₄N₂)

 +  = ( • )

By formula: Ti⁺ + C₄H₄N₂ = (Ti⁺ • C₄H₄N₂)

 +  = ( • )

By formula: Mn⁺ + C₄H₄N₂ = (Mn⁺ • C₄H₄N₂)

 +  = ( • )

By formula: Sc⁺ + C₄H₄N₂ = (Sc⁺ • C₄H₄N₂)

 +  = ( • )

By formula: Mg⁺ + C₄H₄N₂ = (Mg⁺ • C₄H₄N₂)

 +  = ( • )

By formula: V⁺ + C₄H₄N₂ = (V⁺ • C₄H₄N₂)

 +  = ( • )

By formula: Ni⁺ + C₄H₄N₂ = (Ni⁺ • C₄H₄N₂)

 +  = ( • )

By formula: Al⁺ + C₄H₄N₂ = (Al⁺ • C₄H₄N₂)

 +  = ( • )

By formula: Zn⁺ + C₄H₄N₂ = (Zn⁺ • C₄H₄N₂)

 +  = ( • )

By formula: Co⁺ + C₄H₄N₂ = (Co⁺ • C₄H₄N₂)

 +  = ( • )

By formula: Cu⁺ + C₄H₄N₂ = (Cu⁺ • C₄H₄N₂)

Gas phase ion energetics 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 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
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 C₄H₄N₂⁺ (ion structure unspecified)

Electron affinity determinations

Ionization energy determinations

Appearance energy determinations

De-protonation reactions

C₄H₃N₂^- +  =

By formula: C₄H₃N₂^- + H⁺ = C₄H₄N₂

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:
RCD - Robert C. Dunbar
B - John E. Bartmess

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: Al⁺ + C₄H₄N₂ = (Al⁺ • C₄H₄N₂)

 +  = ( • )

By formula: Co⁺ + C₄H₄N₂ = (Co⁺ • C₄H₄N₂)

 +  = ( • )

By formula: Cr⁺ + C₄H₄N₂ = (Cr⁺ • C₄H₄N₂)

 +  = ( • )

By formula: Cu⁺ + C₄H₄N₂ = (Cu⁺ • C₄H₄N₂)

 +  = ( • )

By formula: Fe⁺ + C₄H₄N₂ = (Fe⁺ • C₄H₄N₂)

 +  = ( • )

By formula: Mg⁺ + C₄H₄N₂ = (Mg⁺ • C₄H₄N₂)

 +  = ( • )

By formula: Mn⁺ + C₄H₄N₂ = (Mn⁺ • C₄H₄N₂)

 +  = C₄H₄N₃O^-

By formula: NO^- + C₄H₄N₂ = C₄H₄N₃O^-

 +  = ( • )

By formula: Ni⁺ + C₄H₄N₂ = (Ni⁺ • C₄H₄N₂)

 +  = ( • )

By formula: Sc⁺ + C₄H₄N₂ = (Sc⁺ • C₄H₄N₂)

 +  = ( • )

By formula: Ti⁺ + C₄H₄N₂ = (Ti⁺ • C₄H₄N₂)

 +  = ( • )

By formula: V⁺ + C₄H₄N₂ = (V⁺ • C₄H₄N₂)

 +  = ( • )

By formula: Zn⁺ + C₄H₄N₂ = (Zn⁺ • C₄H₄N₂)

IR Spectrum

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Data compiled by: Coblentz Society, Inc.

• LIQUID (NEAT); PERKIN-ELMER 521 (GRATING); (ADJUSTED subtractcm-1misc); 2 cm^-1 resolution
• SOLUTION (10% IN CCl4 FOR 3800-1370, 10% IN CS2 FOR 1370-450 CM^-1); DOW KBr FOREPRISM-GRATING; DIGITIZED BY NIST FROM HARD COPY (FROM TWO SEGMENTS); 2 cm^-1 resolution

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

• gas

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

UV/Visible spectrum

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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: Victor Talrose, Eugeny B. Stern, Antonina A. Goncharova, Natalia A. Messineva, Natalia V. Trusova, Margarita V. Efimkina

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, polar column, custom temperature program

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References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, Gas Chromatography, NIST Free Links, Notes

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

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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]

Yamaji, Kimura, et al., 1978
Yamaji, A.; Kimura, S.; Kawasaki, H.; Yuki, H., Gas chromatographic analysis of pyrimidine and purine bases by retention indices, Yakugaku Zasshi, 1978, 98, 1, 1536-1541. [all data]

Anderson, Jurel, et al., 1973
Anderson, A.; Jurel, S.; Shymanska, M.; Golender, L., Gas-liquid chromatography of some aliphatic and heterocyclic mono- and pollyfunctional amines. VII. Retention indices of amines in some polar and unpolar stationary phases, Latv. PSR Zinat. Akad. Vestis Kim. Ser., 1973, 1, 51-63. [all data]

Gautzsch and Zinn, 1996
Gautzsch, R.; Zinn, P., Use of incremental models to estimate the retention indexes of aromatic compounds, Chromatographia, 1996, 43, 3/4, 163-176, https://doi.org/10.1007/BF02292946 . [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]

Peng, Yang, et al., 1991
Peng, C.T.; Yang, Z.C.; Ding, S.F., Prediction of rentention idexes. II. Structure-retention index relationship on polar columns, J. Chromatogr., 1991, 586, 1, 85-112, https://doi.org/10.1016/0021-9673(91)80028-F . [all data]

Notes

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• Symbols used in this document:
  

  AE	Appearance energy
  EA	Electron affinity
  IE (evaluated)	Recommended ionization energy
  Tboil	Boiling point
  ΔcH°liquid	Enthalpy of combustion of liquid at standard conditions
  ΔfH°gas	Enthalpy of formation of gas at standard conditions
  ΔfH°liquid	Enthalpy of formation of liquid at standard conditions
  ΔrG°	Free energy of reaction at standard conditions
  ΔrH°	Enthalpy of reaction at standard conditions
  ΔrS°	Entropy of reaction at standard conditions
  ΔvapH°	Enthalpy of vaporization at standard conditions

• Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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