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:
  • Phase change data
  • Gas phase ion energetics data
  • Gas Chromatography
  • References
  • Notes
• Other data available:
  • Gas phase thermochemistry data
  • Condensed phase thermochemistry data
  • Reaction thermochemistry data
  • Mass spectrum (electron ionization)
  • UV/Visible spectrum
• Data at other public NIST sites:
  • Gas Phase Kinetics Database
  • X-ray Photoelectron Spectroscopy Database, version 5.0
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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.

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

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, 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, custom temperature program

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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.

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]

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]

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]

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]

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]

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:
  

  Pc	Critical pressure
  Tboil	Boiling point
  Tc	Critical temperature
  Tfus	Fusion (melting) point
  Ttriple	Triple point temperature
  ΔsubH°	Enthalpy of sublimation at standard conditions
  ρc	Critical density

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