1,3,5-Triazine
- Formula: C3H3N3
- Molecular weight: 81.0760
- IUPAC Standard InChIKey: JIHQDMXYYFUGFV-UHFFFAOYSA-N
- CAS Registry Number: 290-87-9
- 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: s-Triazine; Cyanidine; Vedita 250; s-Triazine-(1,3,5); sym-Triazine
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Gas phase thermochemistry data
Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering data, Gas Chromatography, References, Notes
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 |
---|---|---|---|---|---|
ΔfH°gas | 225.87 ± 0.89 | kJ/mol | Ccr | Bystrom, 1982 | |
ΔfH°gas | 224.7 ± 4.6 | kJ/mol | Cm | Iniguez, Lopez, et al., 1982 |
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 |
---|---|---|---|---|---|
ΔcH°liquid | -1782.6 ± 0.92 | kJ/mol | Ccb | Johnson and Prosen, 1985 | Private communication; ALS |
Quantity | Value | Units | Method | Reference | Comment |
ΔfH°solid | 171.69 ± 0.77 | kJ/mol | Ccr | Bystrom, 1982 | ALS |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°solid | -1780.96 ± 0.67 | kJ/mol | Ccr | Bystrom, 1982 | ALS |
Quantity | Value | Units | Method | Reference | Comment |
S°solid,1 bar | 125.97 | J/mol*K | N/A | van Bommel, van Miltenburg, et al., 1988 | DH |
Constant pressure heat capacity of solid
Cp,solid (J/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
95.57 | 298.15 | van Bommel, van Miltenburg, et al., 1988 | T = 10 to 340 K.; DH |
95.6 | 298.15 | Briels and van Miltenburg, 1979 | T = 160 to 382 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
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 |
---|---|---|---|---|---|
Tboil | 387.2 | K | N/A | Weast and Grasselli, 1989 | BS |
Quantity | Value | Units | Method | Reference | Comment |
Ttriple | 353.44 | K | N/A | Van Bommel, van Miltenburg, et al., 1988 | Crystal phase 1 phase; Uncertainty assigned by TRC = 0.02 K; TRC |
Ttriple | 353.9 | K | N/A | Briels and van Miltenburg, 1979, 2 | Uncertainty assigned by TRC = 0.2 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 38.8 ± 1.9 | kJ/mol | CGC | Lipkind and Chickos, 2009 | Based on data from 342. to 373. K. See also Lipkind and Chickos, 2009, 2.; AC |
ΔvapH° | 55.2 ± 0.1 | kJ/mol | V | Johnson and Prosen, 1985 | Private communication; ALS |
Quantity | Value | Units | Method | Reference | Comment |
ΔsubH° | 54.18 ± 0.19 | kJ/mol | C | Bystrom, 1982 | ALS |
ΔsubH° | 54.2 | kJ/mol | N/A | Bystrom, 1982 | DRB |
ΔsubH° | 54.2 ± 0.2 | kJ/mol | N/A | Bystrom, 1982 | AC |
ΔsubH° | 56.5 ± 2.1 | kJ/mol | V | Iniguez, Lopez, et al., 1982 | ALS |
Enthalpy of sublimation
ΔsubH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
58.2 | 222. | TE,ME | De Wit, Van Miltenburg, et al., 1983 | Based on data from 212. to 229. K.; AC |
Enthalpy of fusion
ΔfusH (kJ/mol) | Temperature (K) | Reference | Comment |
---|---|---|---|
14.56 | 353.4 | Acree, 1991 | AC |
Enthalpy of phase transition
ΔHtrs (kJ/mol) | Temperature (K) | Initial Phase | Final Phase | Reference | Comment |
---|---|---|---|---|---|
0.0740 | 197.7 | crystaline, II | crystaline, I | van Bommel, van Miltenburg, et al., 1988 | First order treatment from 175 K H = 127.4 J/mol First order treatment from 150 K H = 362.8 J/mol Second order treatment; DH |
14.560 | 353.44 | crystaline, I | liquid | van Bommel, van Miltenburg, et al., 1988 | DH |
14.584 | 353.9 | crystaline, I | liquid | Briels and van Miltenburg, 1979 | DH |
Entropy of phase transition
ΔStrs (J/mol*K) | Temperature (K) | Initial Phase | Final Phase | Reference | Comment |
---|---|---|---|---|---|
41.21 | 353.9 | crystaline, I | liquid | Briels and van Miltenburg, 1979 | DH |
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: 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
By formula: Li+ + C3H3N3 = (Li+ • C3H3N3)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 127. ± 13. | kJ/mol | CIDT | Amunugama and Rodgers, 2000 |
By formula: Na+ + C3H3N3 = (Na+ • C3H3N3)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 88. ± 3. | kJ/mol | CIDT | Amunugama and Rodgers, 2000 |
By formula: K+ + C3H3N3 = (K+ • C3H3N3)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 55. ± 3. | kJ/mol | CIDT | Amunugama and Rodgers, 2000 |
Gas phase ion energetics data
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Ion clustering data, Gas Chromatography, References, Notes
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:
LBLHLM - Sharon G. Lias, John E. Bartmess, Joel F. Liebman, John L. Holmes, Rhoda D. Levin, and W. Gary Mallard
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron
B - John E. Bartmess
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Proton affinity (review) | 848.8 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
Quantity | Value | Units | Method | Reference | Comment |
Gas basicity | 819.6 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
Electron affinity determinations
EA (eV) | Method | Reference | Comment |
---|---|---|---|
0.44999 | ETS | Nenner and Schultz, 1975 | G3MP2B3 calculations indicate an EA of ca. 0.1 eV; B |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
9.8 | PE | Shahbaz, Urano, et al., 1984 | LBLHLM |
9.98 | PE | Gleiter, Heilbronner, et al., 1972 | LLK |
10.01 ± 0.01 | PE | Fridh, Asbrink, et al., 1972 | LLK |
10.1 | PE | Brundle, Robin, et al., 1972 | LLK |
10.07 ± 0.05 | EI | Omura, Baba, et al., 1957 | RDSH |
10.51 | PE | Shahbaz, Urano, et al., 1984 | Vertical value; LBLHLM |
Ion clustering 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: Robert C. Dunbar
Note: Please consider using the reaction search for this species. This page allows searching of all reactions involving this species. Searches may be limited to ion clustering reactions. A general reaction search form is also available.
Clustering reactions
By formula: K+ + C3H3N3 = (K+ • C3H3N3)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 55. ± 3. | kJ/mol | CIDT | Amunugama and Rodgers, 2000 |
By formula: Li+ + C3H3N3 = (Li+ • C3H3N3)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 127. ± 13. | kJ/mol | CIDT | Amunugama and Rodgers, 2000 |
By formula: Na+ + C3H3N3 = (Na+ • C3H3N3)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 88. ± 3. | kJ/mol | CIDT | Amunugama and Rodgers, 2000 |
Gas Chromatography
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering data, References, Notes
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
Column type | Active phase | Temperature (C) | I | Reference | Comment |
---|---|---|---|---|---|
Capillary | OV-101 | 110. | 663. | Zhuravleva, 2000 | 50. m/0.3 mm/0.4 μm, He |
Capillary | OV-101 | 110. | 663. | Golovnya, Kuz'menko, et al., 1999 | 50. m/0.3 mm/0.4 μm, He |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering data, Gas Chromatography, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Bystrom, 1982
Bystrom, K.,
The stabilization energy of 1,3,5-triazine derived from measurements of the enthalpies of combustion and sublimation,
J. Chem. Thermodyn., 1982, 14, 865-870. [all data]
Iniguez, Lopez, et al., 1982
Iniguez, J.C.; Lopez, M.E.; McEachern, D.M.,
Vapor pressure and sublimation enthalpy of s-triazine,
Rev. Soc. Quim. Mex., 1982, 26, 122-124. [all data]
Johnson and Prosen, 1985
Johnson, W.H.; Prosen, E.J.,
Determination of the enthalpies of combustion and formation of substituted triazines in an adiabatic rotating bomb calorimeter,
J. Res. NBS, 1985, 90, 295-303. [all data]
van Bommel, van Miltenburg, et al., 1988
van Bommel, M.J.; van Miltenburg, J.C.; Schuijff, A.,
Heat-capacity measurements and thermodynamic functions of 1,3,5-triazine and 1,3,5-trioxane,
J. Chem. Thermodynam., 1988, 20, 397-403. [all data]
Briels and van Miltenburg, 1979
Briels, W.J.; van Miltenburg, J.C.,
s-Triazine: heat capacities between 130 and 380 K, the solid state transition, and the enthalpy of melting,
J. Chem. Phys., 1979, 70, 1064-1066. [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]
Van Bommel, van Miltenburg, et al., 1988
Van Bommel, M.J.; van Miltenburg, J.C.; Schuijff, A.,
Heat Capacity Measurements and Thermodynamic Functions of 1,3,5- Triazine and 1,3,5-Trioxane,
J. Chem. Thermodyn., 1988, 20, 397-403. [all data]
Briels and van Miltenburg, 1979, 2
Briels, W.J.; van Miltenburg, J.C.,
s-Triazine:heat capacities between 130 and 380 K, the solid state transition, and the enthalpy of melting,
J. Chem. Phys., 1979, 70, 1064. [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]
De Wit, Van Miltenburg, et al., 1983
De Wit, H.G.M.; Van Miltenburg, J.C.; De Kruif, C.G.,
Thermodynamic properties of molecular organic crystals containing nitrogen, oxygen, and sulphur 1. Vapour pressures and enthalpies of sublimation,
The Journal of Chemical Thermodynamics, 1983, 15, 7, 651-663, https://doi.org/10.1016/0021-9614(83)90079-4
. [all data]
Acree, 1991
Acree, William E.,
Thermodynamic properties of organic compounds: enthalpy of fusion and melting point temperature compilation,
Thermochimica Acta, 1991, 189, 1, 37-56, https://doi.org/10.1016/0040-6031(91)87098-H
. [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]
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]
Nenner and Schultz, 1975
Nenner, I.; Schultz, G.J.,
Temporary negative ions and electron affinities of benzene and N-heterocyclic molecules: Pyridine, pyridazine, pyrimidine, pyrazine, and s-triazine,
J. Chem. Phys., 1975, 62, 1747. [all data]
Shahbaz, Urano, et al., 1984
Shahbaz, M.; Urano, S.; LeBreton, P.R.; Rossman, M.A.; Hosmane, R.S.; Leonard, N.J.,
Tri-s-triazine: Synthesis, chemical behavior and spectroscopic and theoretical probes of valence orbital structure,
J. Am. Chem. Soc., 1984, 106, 2805. [all data]
Gleiter, Heilbronner, et al., 1972
Gleiter, R.; Heilbronner, E.; Hornung, V.,
Photoelectron spectra of azabenzenes azanaphthalenes: I. Pyridine, diazines s-triazine and s-tetrazine,
Helv. Chim. Acta, 1972, 55, 255. [all data]
Fridh, Asbrink, et al., 1972
Fridh, C.; Asbrink, L.; Jonsson, B.O.; Lindholm, E.,
Rydberg series in small molecules. XIV. Photoelectron, UV, mass and electron impact spectra of s-triazine,
Int. J. Mass Spectrom. Ion Phys., 1972, 8, 85. [all data]
Brundle, Robin, et al., 1972
Brundle, C.R.; Robin, M.B.; Kuebler, N.A.,
Perfluoro effect in photoelectron spectroscopy. II. Aromatic molecules,
J. Am. Chem. Soc., 1972, 94, 1466. [all data]
Omura, Baba, et al., 1957
Omura, I.; Baba, H.; Higasi, K.; Kanaoka, Y.,
Ionization potentials of some organic molecules. V.Heterocyclic compo&jnds containing nitrogen,
Bull. Chem. Soc. Japan, 1957, 30, 633. [all data]
Zhuravleva, 2000
Zhuravleva, I.L.,
Evaluation of the polarity and boiling points of nitrogen-containing heterocyclic compounds by gas chromatography,
Russ. Chem. Bull. (Engl. Transl.), 2000, 49, 2, 325-328, https://doi.org/10.1007/BF02494682
. [all data]
Golovnya, Kuz'menko, et al., 1999
Golovnya, R.V.; Kuz'menko, T.E.; Zhuravleva, I.L.,
Gas chromatographic indicator of the ability of five- and six-membered heterocyclic nitrogen-containing compounds for self-association in pure liquids,
Russ. Chem. Bull. (Engl. Transl.), 1999, 48, 4, 726-729, https://doi.org/10.1007/BF02496256
. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering data, Gas Chromatography, References
- Symbols used in this document:
Cp,solid Constant pressure heat capacity of solid EA Electron affinity S°solid,1 bar Entropy of solid at standard conditions (1 bar) Tboil Boiling point Ttriple Triple point temperature ΔHtrs Enthalpy of phase transition ΔStrs Entropy of phase transition ΔcH°liquid Enthalpy of combustion of liquid at standard conditions 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 ΔfusH Enthalpy of fusion ΔrH° Enthalpy of reaction at standard conditions ΔsubH Enthalpy of sublimation ΔsubH° Enthalpy of sublimation at standard conditions ΔvapH° Enthalpy of vaporization at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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