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Pyrazine

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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

Quantity Value Units Method Reference Comment
Deltafgas196.1 ± 1.5kJ/molCcbTjebbes, 1962 

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

Quantity Value Units Method Reference Comment
Deltafliquid139.8 ± 1.2kJ/molCcbTjebbes, 1962ALS
Quantity Value Units Method Reference Comment
Deltacliquid-2285.5 ± 1.2kJ/molCcbTjebbes, 1962ALS

Constant pressure heat capacity of solid

Cp,solid (J/mol*K) Temperature (K) Reference Comment
180.298.Boyd, Comper, et al., 1979crystaline, III phase; T = 295 to 312 K. Data graphically only.; 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
AC - William E. Acree, Jr., James S. Chickos
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DRB - Donald R. Burgess, Jr.
DH - Eugene S. Domalski and Elizabeth D. Hearing

Quantity Value Units Method Reference Comment
Tboil388.7KN/AAldrich Chemical Company Inc., 1990BS
Tboil388.65KN/AAnderson and Shimanskaya, 1969Uncertainty assigned by TRC = 1. K; TRC
Tboil390.35KN/ALecat, 1947Uncertainty assigned by TRC = 0.5 K; TRC
Quantity Value Units Method Reference Comment
Tfus324.KN/ABougeard, LeCalve, et al., 1978Crystal phase 1 phase; Uncertainty assigned by TRC = 0.1 K; TRC
Tfus320.15KN/ABruhl, 1897Uncertainty assigned by TRC = 1. K; TRC
Tfus334.05KN/ABruhl, 1897Uncertainty assigned by TRC = 6. K; TRC
Quantity Value Units Method Reference Comment
Deltavap40.5 ± 1.7kJ/molCGCLipkind and Chickos, 2009Based on data from 342. - 373. K. See also Lipkind and Chickos, 2009, 2.; AC
Deltavap56.27 ± 0.46kJ/molCTjebbes, 1962ALS
Deltavap56.3kJ/molN/ATjebbes, 1962DRB

Reduced pressure boiling point

Tboil (K) Pressure (bar) Reference Comment
388.71.02Weast and Grasselli, 1989BS

Enthalpy of vaporization

DeltavapH (kJ/mol) Temperature (K) Method Reference Comment
38.8 ± 0.1340.EBSteele, Chirico, et al., 2002Based on data from 354. - 426. K.; AC
36.5 ± 0.2380.EBSteele, Chirico, et al., 2002Based on data from 354. - 426. K.; AC
34.1 ± 0.4420.EBSteele, Chirico, et al., 2002Based on data from 354. - 426. K.; AC
37.9352.N/ASakoguchi, Ueoka, et al., 1995Based on data from 332. - 373. K.; AC

Enthalpy of sublimation

DeltasubH (kJ/mol) Temperature (K) Reference Comment
56.2303.Sakoguchi, Ueoka, et al., 1995Based on data from 288. - 317. K.; AC

Enthalpy of fusion

DeltafusH (kJ/mol) Temperature (K) Method Reference Comment
14.78325.4ACChirico, Knipmeyer, et al., 2003Based on data from 5. - 380. K.; AC
12.95328.2N/ABougeard, Calve, et al., 1978AC

Enthalpy of phase transition

DeltaHtrs (kJ/mol) Temperature (K) Initial Phase Final Phase Reference Comment
0.969300.6crystaline, IIIcrystaline, IIBoyd, Comper, et al., 1979DH
0.060310.crystaline, IIcrystaline, IBoyd, Comper, et al., 1979DH

Entropy of phase transition

DeltaStrs (J/mol*K) Temperature (K) Initial Phase Final Phase Reference Comment
3.22300.6crystaline, IIIcrystaline, IIBoyd, Comper, et al., 1979DH
0.2310.crystaline, IIcrystaline, IBoyd, Comper, et al., 1979DH

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 as indicated in comments:
B - John E. Bartmess
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
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

C4H3N2- + Hydrogen cation = Pyrazine

By formula: C4H3N2- + H+ = C4H4N2

Quantity Value Units Method Reference Comment
Deltar1643. ± 10.kJ/molTDEqMeot-ner and Kafafi, 1988gas phase; anchored to 88MEO scale, not the "87 acidity scale". The Kiefer, Zhang, et al., 1997 BDE is for ortho.; B
Quantity Value Units Method Reference Comment
Deltar1604.6 ± 1.7kJ/molN/AWren, Vogelhuber, et al., 2012gas phase; B
Deltar1603. ± 8.4kJ/molTDEqMeot-ner and Kafafi, 1988gas phase; anchored to 88MEO scale, not the "87 acidity scale". The Kiefer, Zhang, et al., 1997 BDE is for ortho.; B

3Hydrogen + Pyrazine = Piperazine

By formula: 3H2 + C4H4N2 = C4H10N2

Quantity Value Units Method Reference Comment
Deltar207.2 ± 2.8kJ/molChydHafelinger and Steinmann, 1977liquid phase; solvent: Acetic acid; ALS

Lithium ion (1+) + Pyrazine = (Lithium ion (1+) bullet Pyrazine)

By formula: Li+ + C4H4N2 = (Li+ bullet C4H4N2)

Quantity Value Units Method Reference Comment
Deltar149. ± 14.kJ/molCIDTAmunugama and Rodgers, 2000RCD

Sodium ion (1+) + Pyrazine = (Sodium ion (1+) bullet Pyrazine)

By formula: Na+ + C4H4N2 = (Na+ bullet C4H4N2)

Quantity Value Units Method Reference Comment
Deltar108. ± 3.kJ/molCIDTAmunugama and Rodgers, 2000RCD

Potassium ion (1+) + Pyrazine = (Potassium ion (1+) bullet Pyrazine)

By formula: K+ + C4H4N2 = (K+ bullet C4H4N2)

Quantity Value Units Method Reference Comment
Deltar67. ± 4.kJ/molCIDTAmunugama and Rodgers, 2000RCD

IR 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: Coblentz Society, Inc.

Condensed Phase Spectrum

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IR spectrum
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Notice: Except where noted, spectra from this collection were measured on dispersive instruments, often in carefully selected solvents, and hence may differ in detail from measurements on FTIR instruments or in other chemical environments. More information on the manner in which spectra in this collection were collected can be found here.

Notice: Concentration information is not available for this spectrum and, therefore, molar absorptivity values cannot be derived.

Additional Data

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Owner COPYRIGHT (C) 1988 by COBLENTZ SOCIETY INC.
Collection (C) 2018 copyright by the U.S. Secretary of Commerce
on behalf of the United States of America. All rights reserved.
Origin DOW CHEMICAL COMPANY
Source reference COBLENTZ NO. 5739
Date 1965/11/12
State SOLUTION (10% CCl4 FOR 2.6-7.5, 10% CS2 FOR 7.5-24 MICRON)
Instrument BECKMAN IR-9 (GRATING)
Instrument parameters ORDER CHANGES: 670, 1200, 2000 CM-1
Path length 0.012 CM, 0.012 CM
SPECTRAL CONTAMINATION DUE TO CS2 AROUND 400, 850 AND CCl4 AROUND 1550 CM-1 HAVE BEEN SUBTRACTED
Resolution 2
Sampling procedure TRANSMISSION
Data processing DIGITIZED BY COBLENTZ SOCIETY (BATCH I) FROM HARD COPY
Melting point 53 C
Boiling point 116 C

This IR spectrum is from the Coblentz Society's evaluated infrared reference spectra collection.


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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Mass spectrum
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Additional Data

View image of digitized spectrum (can be printed in landscape orientation).

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Owner NIST Mass Spectrometry Data Center
Collection (C) 2014 copyright by the U.S. Secretary of Commerce
on behalf of the United States of America. All rights reserved.
Origin Japan AIST/NIMC Database- Spectrum MS-NW-5010
NIST MS number 230075

All mass spectra in this site (plus many more) are available from the NIST/EPA/NIH Mass Spectral Library. Please see the following for information about the library and its accompanying search program.


References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, IR Spectrum, 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.

Tjebbes, 1962
Tjebbes, J., The heats of combustion and formation of the three diazines and their resonance energies, Acta Chem. Scand., 1962, 16, 916-921. [all data]

Boyd, Comper, et al., 1979
Boyd, R.K.; Comper, J.; Ferguson, G., Entropy changes and structural implications for crystalline phases of pyrazine, Can. J. Chem., 1979, 57, 3056-3060. [all data]

Aldrich Chemical Company Inc., 1990
Aldrich Chemical Company Inc., Catalog Handbook of Fine Chemicals, Aldrich Chemical Company, Inc., Milwaukee WI, 1990, 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]

Lecat, 1947
Lecat, M., Some azeotropes of which one constituant is heterocyclic nitrogen, Ann. Soc. Sci. Bruxelles, Ser. 1, 1947, 61, 73. [all data]

Bougeard, LeCalve, et al., 1978
Bougeard, D.; LeCalve, N.; Novak, A.; Bachanh, N., Phase transitions of pyrazine., Mol. Cryst. Liq. Cryst., 1978, 44, 113. [all data]

Bruhl, 1897
Bruhl, J.W., Spectrochemistry of nitrogen containing compounds V, Z. Phys. Chem., Stoechiom. Verwandtschaftsl., 1897, 22, 373. [all data]

Lipkind and Chickos, 2009
Lipkind, Dmitri; Chickos, James S., An examination of the vaporization enthalpies and vapor pressures of pyrazine, pyrimidine, pyridazine, and 1,3,5-triazine, Struct Chem, 2009, 20, 1, 49-58, https://doi.org/10.1007/s11224-008-9389-5 . [all data]

Lipkind and Chickos, 2009, 2
Lipkind, D.; Chickos, J.S., , Abstract from 38th Great Lakes Regional Meeting of the American Chemical Society, May 13-16, Chicago, IL, 2009, GLRM-275. [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]

Steele, Chirico, et al., 2002
Steele, W.V.; Chirico, R.D.; Knipmeyer, S.E.; Nguyen, A., Measurements of Vapor Pressure, Heat Capacity, and Density along the Saturation Line for «gamma»-Caprolactam, Pyrazine, 1,2-Propanediol, Triethylene Glycol, Phenyl Acetylene, and Diphenyl Acetylene, J. Chem. Eng. Data, 2002, 47, 4, 689-699, https://doi.org/10.1021/je010085z . [all data]

Sakoguchi, Ueoka, et al., 1995
Sakoguchi, Akihiro; Ueoka, Ryuichi; Kato, Yasuo; Arai, Yasuhiko, Vapor Pressures of Alkylpyridines and Alkylpyrazines., KAGAKU KOGAKU RONBUNSHU, 1995, 21, 1, 219-223, https://doi.org/10.1252/kakoronbunshu.21.219 . [all data]

Chirico, Knipmeyer, et al., 2003
Chirico, R.D.; Knipmeyer, S.E.; Steele, W.V., Heat capacities, enthalpy increments, and derived thermodynamic functions for pyrazine between the temperatures 5K and 380K, The Journal of Chemical Thermodynamics, 2003, 35, 7, 1059-1072, https://doi.org/10.1016/S0021-9614(03)00041-7 . [all data]

Bougeard, Calve, et al., 1978
Bougeard, D.; Calve, N. Le; Novak, A.; Nguyen-ba-chanh, A., Phase Transitions of Pyrazine, GMCL, 1978, 44, 1, 113-123, https://doi.org/10.1080/15421407808083935 . [all data]

Meot-ner and Kafafi, 1988
Meot-ner, M.; Kafafi, S.A., Carbon Acidities of Aromatic Compounds, J. Am. Chem. Soc., 1988, 110, 19, 6297, https://doi.org/10.1021/ja00227a003 . [all data]

Kiefer, Zhang, et al., 1997
Kiefer, J.H.; Zhang, Q.; Kern, R.D.; Yao, J.; Jursic, B., Pyrolysis of Aromatic Azines: Pyrazine, Pyrimidine, and Pyridine, J. Phys. Chem. A, 1997, 101, 38, 7061, https://doi.org/10.1021/jp970211z . [all data]

Wren, Vogelhuber, et al., 2012
Wren, S.W.; Vogelhuber, K.M.; Garver, J.M.; Kato, S.; Sheps, L.; Bierbaum, V.M.; Lineberger, W.C., C-H Bond Strengths and Acidities in Aromatic Systems: Effects of Nitrogen Incorporation in Mono-, Di-, and Triazines, J. Am. Chem. Soc., 2012, 134, 15, 6584-6595, https://doi.org/10.1021/ja209566q . [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]

Amunugama and Rodgers, 2000
Amunugama, R.; Rodgers, M.T., Absolute Alkali Metal Ion Binding Affinities of Several Azines Determined by Threshold Collision-Induced Dissociation and Ab Initio Theory, Int. J. Mass Spectrom., 2000, 195/196, 439, https://doi.org/10.1016/S1387-3806(99)00145-1 . [all data]


Notes

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, IR Spectrum, Mass spectrum (electron ionization), References