Piperazine

• Formula: C₄H₁₀N₂
• Molecular weight: 86.1356
• IUPAC Standard InChI: InChI=1S/C4H10N2/c1-2-6-4-3-5-1/h5-6H,1-4H2 Copy

  
• IUPAC Standard InChIKey: GLUUGHFHXGJENI-UHFFFAOYSA-N Copy
• CAS Registry Number: 110-85-0
• 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: Hexahydropyrazine; Antiren; Diethylenediamine; Diethyleneimine; Dispermine; Eraverm; Lumbrical; Piperazidine; Pipersol; Pyrazine hexahydride; Pyrazine, hexahydro-; Uvilon; Worm-A-Ton; Wurmirazin; 1,4-Diazacyclohexane; 1,4-Piperazine; 1,4-Diethylenediamine; Hexahydro-1,4-diazine; Piperazine, anhydrous; Asca-Trol No. 3; Piperazin; UN 2579; Vermex; Upixon; NSC 474
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• Information on this page:
  • Gas phase thermochemistry data
  • Condensed phase thermochemistry data
  • Phase change data
  • Reaction thermochemistry data
  • Gas phase ion energetics data
  • Mass spectrum (electron ionization)
  • References
  • Notes
• Other data available:
  • UV/Visible spectrum
  • Gas Chromatography
• Data at other public NIST sites:
  • Gas Phase Kinetics Database
  • X-ray Photoelectron Spectroscopy Database, version 5.0
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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 as indicated in comments:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DRB - Donald R. Burgess, Jr.

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 as indicated in comments:
DH - Eugene S. Domalski and Elizabeth D. Hearing
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Constant pressure heat capacity of liquid

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
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
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 by: 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.

Individual Reactions

 +  =

By formula: C₄H₁₀N₂ + C₂H₅N = C₆H₁₅N₃

3 +  =

By formula: 3H₂ + C₄H₄N₂ = C₄H₁₀N₂

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

Data compiled as indicated in comments:
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi

View reactions leading to C₄H₁₀N₂⁺ (ion structure unspecified)

Ionization energy determinations

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

References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Mass spectrum (electron ionization), Notes

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

An, Zhang, et al., 1981
An, X.-W.; Zhang, Z.-L.; Wang, S.-N.; Yan, J.-Q.; Hu, R.-H., Investigation on bond energies: the heat of combustion of hippuric acid, piperazine and azacycloheptane, Acta Chim. Sin., 1981, 39, 485-492. [all data]

Bedford, Beezer, et al., 1963
Bedford, A.F.; Beezer, A.E.; Mortimer, C.T., Heats of formation and bond energies. Part X. 1,2,5,6-tetrahydropyridine, piperidine, and piperazine, J. Chem. Soc., 1963, 2039-2043. [all data]

Bobylev, Kamskaya, et al., 1988
Bobylev, V.A.; Kamskaya, O.I.; Kossoi, A.A.; Koludarova, E.Yu., Investigation of the heat capacity of ethyleneamines by differential scanning calorimetry, Zhur. Obshch. Khim., 1988, 58, 2536-2538. [all data]

Weast and Grasselli, 1989
CRC Handbook of Data on Organic Compounds, 2nd Editon, Weast,R.C and Grasselli, J.G., ed(s)., CRC Press, Inc., Boca Raton, FL, 1989, 1. [all data]

Anderson and Shimanskaya, 1969
Anderson, A.A.; Shimanskaya, M.V., Gas-Liquid Chromatography of some Aliphatic and Heterocyclic Polyfunctional Amines: II. Solution Thermodyn. of Amines in Fix. Phas., Latv. PSR Zinat. Akad. Vestis, Kim. Ser., 1969, No. 5, 527. [all data]

Aroney and Le Fevre, 1960
Aroney, M.; Le Fevre, R.J.W., Molecular polarizability. The conformation of various n-substituted anilines, piperidines, and piperazines, J. Chem. Soc., 1960, 1960, 2161. [all data]

Anonymous, 1957
Anonymous, R., , Am. Pet. Inst. Res. Proj. 6, Carnegie-Mellon Univ., 1957. [all data]

Witschonke, 1954
Witschonke, C.R., Freezing point and purity data for some organic compounds, Anal. Chem., 1954, 26, 562-4. [all data]

Steele, Chirico, et al., 1997
Steele, W.V.; Chirico, R.D.; Knipmeyer, S.E.; Nguyen, A.; Smith, N.K., Thermocynamic Properties and Ideal-Gas Enthalpies of Formation for Carbonate, Piperazine, Hexachloroprop-1-ene, Tetrakis(dimethylamino) ethylene, N,N'-Bis(2-hydroxyethyl)ethylenediamine, and 1,2,4-Tr, J. Chem. Eng. Data, 1997, 42, 1037-52. [all data]

Dalin, Bobylev, et al., 1988
Dalin, A.R.; Bobylev, V.A.; Suslikov, V.F.; Kamskaya, O.I.; Tereshchenko, G.F., Nucleophilic cleavage and the formation of saturated heterocycles. VII. Kinetic and thermochemical study of reactions of aziridine with ethylene amines, J. Gen. Chem. USSR, 1988, 58, 1868-1871. [all data]

Hafelinger and Steinmann, 1977
Hafelinger, G.; Steinmann, L., Heat of hydrogenation of compounds containing isolated and conjugted C=N bouble bonds, Angew. Chem. Int. Ed. Engl., 1977, 16, 47-48. [all data]

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]

Nelsen and Buschek, 1974
Nelsen, S.F.; Buschek, J.M., Photoelectron spectra of some cyclic di- and polyamines. Lone pair-lone pair interaction in 1,3- and 1,4-diamines, J. Am. Chem. Soc., 1974, 96, 7930. [all data]

Rademacher, 1973
Rademacher, P., Photoelectron spectra and conformation of hydrazine derivatives, Angew. Chem. Int. Ed. Engl., 1973, 12, 408. [all data]

Notes

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• Symbols used in this document:
  

  Cp,liquid	Constant pressure heat capacity of liquid
  Pc	Critical pressure
  Tboil	Boiling point
  Tc	Critical temperature
  Tfus	Fusion (melting) point
  Ttriple	Triple point temperature
  ΔcH°solid	Enthalpy of combustion of solid at standard conditions
  ΔfH°gas	Enthalpy of formation of gas at standard conditions
  ΔfH°solid	Enthalpy of formation of solid at standard conditions
  ΔrH°	Enthalpy of reaction at standard conditions
  ΔsubH°	Enthalpy of sublimation at standard conditions
  ρc	Critical density

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