Piperazine

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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
Δfsolid-9.99 ± 0.27kcal/molCcbAn, Zhang, et al., 1981ALS
Δfsolid-10.90 ± 0.38kcal/molCcbBedford, Beezer, et al., 1963ALS
Quantity Value Units Method Reference Comment
Δcsolid-707.79 ± 0.27kcal/molCcbAn, Zhang, et al., 1981ALS
Δcsolid-706.88 ± 0.38kcal/molCcbBedford, Beezer, et al., 1963ALS

Constant pressure heat capacity of liquid

Cp,liquid (cal/mol*K) Temperature (K) Reference Comment
56.6413.Bobylev, Kamskaya, et al., 1988T = 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
Tboil419.2KN/AWeast and Grasselli, 1989BS
Tboil418.15KN/AAnderson and Shimanskaya, 1969Uncertainty assigned by TRC = 2. K; TRC
Tboil415.15KN/AAroney and Le Fevre, 1960Uncertainty assigned by TRC = 1.5 K; TRC
Quantity Value Units Method Reference Comment
Tfus383.2KN/AAnonymous, 1957Uncertainty assigned by TRC = 0.6 K; TRC
Tfus383.46KN/AWitschonke, 1954Uncertainty assigned by TRC = 0.3 K; TRC
Tfus384.55KN/AWitschonke, 1954Uncertainty assigned by TRC = 0.2 K; TRC
Quantity Value Units Method Reference Comment
Ttriple384.6KN/ASteele, Chirico, et al., 1997Uncertainty assigned by TRC = 0.3 K; TRC
Quantity Value Units Method Reference Comment
Tc661.KN/ASteele, Chirico, et al., 1997Uncertainty assigned by TRC = 2. K; TRC
Quantity Value Units Method Reference Comment
Pc57.24atmN/ASteele, Chirico, et al., 1997Uncertainty assigned by TRC = 1.97 atm; derived from fit of obs. vapor pressure; TRC
Quantity Value Units Method Reference Comment
ρc3.738mol/lN/ASteele, Chirico, et al., 1997Uncertainty assigned by TRC = 0.29 mol/l; TRC
Quantity Value Units Method Reference Comment
Δsub16.0 ± 1.5kcal/molEAn, Zhang, et al., 1981ALS
Δsub16.0kcal/molN/AAn, Zhang, et al., 1981DRB

In addition to the Thermodynamics Research Center (TRC) data available from this site, much more physical and chemical property data is available from the following TRC products:


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

Piperazine + Ethylenimine = 1-Piperazineethanamine

By formula: C4H10N2 + C2H5N = C6H15N3

Quantity Value Units Method Reference Comment
Δr20.5 ± 0.5kcal/molCmDalin, Bobylev, et al., 1988liquid phase; solvent: Aqueous HCl; Kinetic

3Hydrogen + Pyrazine = Piperazine

By formula: 3H2 + C4H4N2 = C4H10N2

Quantity Value Units Method Reference Comment
Δr49.52 ± 0.67kcal/molChydHafelinger and Steinmann, 1977liquid 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)225.5kcal/molN/AHunter and Lias, 1998HL
Quantity Value Units Method Reference Comment
Gas basicity218.6kcal/molN/AHunter and Lias, 1998HL

Ionization energy determinations

IE (eV) Method Reference Comment
8.98PENelsen and Buschek, 1974Vertical value; LLK
8.72PERademacher, 1973Vertical 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

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