Piperazine
- Formula: C4H10N2
- Molecular weight: 86.1356
- IUPAC Standard InChIKey: GLUUGHFHXGJENI-UHFFFAOYSA-N
- 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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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
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°solid | -9.99 ± 0.27 | kcal/mol | Ccb | An, Zhang, et al., 1981 | ALS |
ΔfH°solid | -10.90 ± 0.38 | kcal/mol | Ccb | Bedford, Beezer, et al., 1963 | ALS |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°solid | -707.79 ± 0.27 | kcal/mol | Ccb | An, Zhang, et al., 1981 | ALS |
ΔcH°solid | -706.88 ± 0.38 | kcal/mol | Ccb | Bedford, Beezer, et al., 1963 | ALS |
Constant pressure heat capacity of liquid
Cp,liquid (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
56.6 | 413. | Bobylev, Kamskaya, et al., 1988 | T = 413 to 473 K.; DH |
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.
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tboil | 419.2 | K | N/A | Weast and Grasselli, 1989 | BS |
Tboil | 418.15 | K | N/A | Anderson and Shimanskaya, 1969 | Uncertainty assigned by TRC = 2. K; TRC |
Tboil | 415.15 | K | N/A | Aroney and Le Fevre, 1960 | Uncertainty assigned by TRC = 1.5 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 383.2 | K | N/A | Anonymous, 1957 | Uncertainty assigned by TRC = 0.6 K; TRC |
Tfus | 383.46 | K | N/A | Witschonke, 1954 | Uncertainty assigned by TRC = 0.3 K; TRC |
Tfus | 384.55 | K | N/A | Witschonke, 1954 | Uncertainty assigned by TRC = 0.2 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Ttriple | 384.6 | K | N/A | Steele, Chirico, et al., 1997 | Uncertainty assigned by TRC = 0.3 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Tc | 661. | K | N/A | Steele, Chirico, et al., 1997 | Uncertainty assigned by TRC = 2. K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Pc | 57.24 | atm | N/A | Steele, Chirico, et al., 1997 | Uncertainty assigned by TRC = 1.97 atm; derived from fit of obs. vapor pressure; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ρc | 3.738 | mol/l | N/A | Steele, Chirico, et al., 1997 | Uncertainty assigned by TRC = 0.29 mol/l; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔsubH° | 16.0 ± 1.5 | kcal/mol | E | An, Zhang, et al., 1981 | ALS |
ΔsubH° | 16.0 | kcal/mol | N/A | An, Zhang, et al., 1981 | DRB |
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
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 20.5 ± 0.5 | kcal/mol | Cm | Dalin, Bobylev, et al., 1988 | liquid phase; solvent: Aqueous HCl; Kinetic |
By formula: 3H2 + C4H4N2 = C4H10N2
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 49.52 ± 0.67 | kcal/mol | Chyd | Hafelinger and Steinmann, 1977 | liquid phase; solvent: Acetic acid |
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)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Proton affinity (review) | 225.5 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
Quantity | Value | Units | Method | Reference | Comment |
Gas basicity | 218.6 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
8.98 | PE | Nelsen and Buschek, 1974 | Vertical value; LLK |
8.72 | PE | Rademacher, 1973 | Vertical value; LLK |
References
Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, 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
Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, References
- 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°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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