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1,3-Diazine

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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
Deltafgas46.80 ± 0.36kcal/molCcrNabavian, Sabbah, et al., 1977Reanalyzed by Pedley, Naylor, et al., 1986, Original value = 46.15 ± 0.47 kcal/mol
Deltafgas46.83 ± 0.33kcal/molCcbTjebbes, 1962Reanalyzed by Cox and Pilcher, 1970, Original value = 46.99 ± 0.24 kcal/mol

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 by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Quantity Value Units Method Reference Comment
Deltafliquid34.23 ± 0.44kcal/molCcrNabavian, Sabbah, et al., 1977 
Deltafliquid35.04 ± 0.20kcal/molCcbTjebbes, 1962 
Quantity Value Units Method Reference Comment
Deltacliquid-547.06 ± 0.42kcal/molCcrNabavian, Sabbah, et al., 1977 
Deltacliquid-547.88 ± 0.20kcal/molCcbTjebbes, 1962 

Reaction thermochemistry data

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry 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 as indicated in comments:
MS - José A. Martinho Simões
B - John E. Bartmess
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

C10H5CrNO5 (solution) + Carbon monoxide (solution) = Chromium hexacarbonyl (solution) + 1,3-Diazine (solution)

By formula: C10H5CrNO5 (solution) + CO (solution) = C6CrO6 (solution) + C4H4N2 (solution)

Quantity Value Units Method Reference Comment
Deltar-14.8kcal/molKinSWovkulich and Atwood, 1980solvent: Hexane; The data rely on the enthalpy and entropy of activation for the forward reaction, 25.4 ± 1.1 kcal/mol and 13.0±14.6 J/(mol K) Dennenberg and Darensbourg, 1972, and also on the enthalpy and entropy of activation for the Cr-CO dissociation in Cr(CO)6, 40.20 ± 0.60 kcal/mol and 94.6±6.3 J/(mol K) Graham and Angelici, 1967. The latter data were obtained in decalin; MS

Tungsten hexacarbonyl (cr) + 1,3-Diazine (l) = C10H5NO5W (cr) + Carbon monoxide (g)

By formula: C6O6W (cr) + C4H4N2 (l) = C10H5NO5W (cr) + CO (g)

Quantity Value Units Method Reference Comment
Deltar8.27kcal/molN/ANakashima and Adamson, 1982The reaction enthalpy was calculated from the enthalpy of the reaction W(CO)6(solution) + py(solution) = W(CO)5(py)(solution) + CO(solution) in cyclohexane, 6.55 ± 0.69 kcal/mol, together with the enthalpies of solution of W(CO)6(cr), W(CO)5(py)(cr), and py(l), 35.7, 36.4, and 1.9 kcal/mol, respectively Nakashima and Adamson, 1982.; MS

C4H3N2- + Hydrogen cation = 1,3-Diazine

By formula: C4H3N2- + H+ = C4H4N2

Quantity Value Units Method Reference Comment
Deltar385.2 ± 2.5kcal/molTDEqMeot-ner and Kafafi, 1988gas phase; Acid: pyrimidine. Anchored to 88MEO scale, not "87 acidity scale; B
Quantity Value Units Method Reference Comment
Deltar376.80 ± 0.70kcal/molN/AWren, Vogelhuber, et al., 2012gas phase; B
Deltar376.9 ± 2.0kcal/molTDEqMeot-ner and Kafafi, 1988gas phase; Acid: pyrimidine. Anchored to 88MEO scale, not "87 acidity scale; B

Tungsten hexacarbonyl (solution) + 1,3-Diazine (solution) = C10H5NO5W (solution) + Carbon monoxide (solution)

By formula: C6O6W (solution) + C4H4N2 (solution) = C10H5NO5W (solution) + CO (solution)

Quantity Value Units Method Reference Comment
Deltar6.55 ± 0.69kcal/molPCNakashima and Adamson, 1982solvent: Cyclohexane; MS
Deltar5.95 ± 0.69kcal/molPCNakashima and Adamson, 1982solvent: Benzene; MS
Deltar4.40 ± 0.1kcal/molPCNakashima and Adamson, 1982solvent: Tetrahydrofuran; MS

C39H68O3P2W (solution) + 1,3-Diazine (solution) = C44H71NO3P2W (solution) + Hydrogen (g)

By formula: C39H68O3P2W (solution) + C4H4N2 (solution) = C44H71NO3P2W (solution) + H2 (g)

Quantity Value Units Method Reference Comment
Deltar-9.49 ± 0.50kcal/molRSCGonzalez, Zhang, et al., 1988solvent: Toluene; MS
Deltar-9.99 ± 0.50kcal/molRSCGonzalez, Zhang, et al., 1988solvent: Tetrahydrofuran; MS

C14H10CrN2O4 (cr) = 21,3-Diazine (g) + 4Carbon monoxide (g) + chromium (cr)

By formula: C14H10CrN2O4 (cr) = 2C4H4N2 (g) + 4CO (g) + Cr (cr)

Quantity Value Units Method Reference Comment
Deltar>47.6kcal/molTD-HFCAdedeji, Connor, et al., 1978The reaction enthalpy is a low limit Adedeji, Connor, et al., 1978.; MS

C8H6MoO3 (solution) + 31,3-Diazine (solution) = C18H15MoN3O3 (solution) + 1,3-Cyclopentadiene (solution)

By formula: C8H6MoO3 (solution) + 3C4H4N2 (solution) = C18H15MoN3O3 (solution) + C5H6 (solution)

Quantity Value Units Method Reference Comment
Deltar-16.7 ± 0.69kcal/molRSCNolan, Hoff, et al., 1985solvent: Pyridine; Reaction temperature: 323 K; MS

Nitric oxide anion + 1,3-Diazine = C4H4N3O-

By formula: NO- + C4H4N2 = C4H4N3O-

Quantity Value Units Method Reference Comment
Deltar16.6 ± 2.3kcal/molN/ALe Barbu, Schiedt, et al., 2002gas phase; Affinity is difference in EAs of lesser solvated species; B

C9H9CrN3O3 (solution) + 31,3-Diazine (solution) = C18H15CrN3O3 (solution) + 3Acetonitrile (solution)

By formula: C9H9CrN3O3 (solution) + 3C4H4N2 (solution) = C18H15CrN3O3 (solution) + 3C2H3N (solution)

Quantity Value Units Method Reference Comment
Deltar-11.5 ± 0.91kcal/molRSCMukerjee, Lang, et al., 1992solvent: Tetrahydrofuran; MS

C7H9Cl2NPd (solution) + 1,3-Diazine (l) = (PdCl2(C5H5N)2) (solution) + Ethylene (solution)

By formula: C7H9Cl2NPd (solution) + C4H4N2 (l) = (PdCl2(C5H5N)2) (solution) + C2H4 (solution)

Quantity Value Units Method Reference Comment
Deltar-13.8 ± 0.41kcal/molRSCPartenheimer and Durham, 1974solvent: Dichloromethane; MS

C10H5NO5W (cr) + Carbon monoxide (g) = Tungsten hexacarbonyl (g) + 1,3-Diazine (g)

By formula: C10H5NO5W (cr) + CO (g) = C6O6W (g) + C4H4N2 (g)

Quantity Value Units Method Reference Comment
Deltar20. ± 2.4kcal/molDSCDaamen, van der Poel, et al., 1979Please also see Meester, Vriends, et al., 1976.; MS

C12H16CrO5 (solution) + 1,3-Diazine (solution) = Heptane (solution) + C10H5CrNO5 (solution)

By formula: C12H16CrO5 (solution) + C4H4N2 (solution) = C7H16 (solution) + C10H5CrNO5 (solution)

Quantity Value Units Method Reference Comment
Deltar-20.1 ± 0.41kcal/molPACYang, Vaida, et al., 1988solvent: Heptane; MS

C39H66MoO3P3 (solution) + 1,3-Diazine (solution) = C44H71MoNO3P2 (solution)

By formula: C39H66MoO3P3 (solution) + C4H4N2 (solution) = C44H71MoNO3P2 (solution)

Quantity Value Units Method Reference Comment
Deltar-16.9 ± 0.60kcal/molRSCZhang, Gonzalez, et al., 1991solvent: Toluene; MS

Molybdenum hexacarbonyl (cr) + 31,3-Diazine (g) = C18H15MoN3O3 (cr) + 3Carbon monoxide (g)

By formula: C6MoO6 (cr) + 3C4H4N2 (g) = C18H15MoN3O3 (cr) + 3CO (g)

Quantity Value Units Method Reference Comment
Deltar-12.0 ± 1.7kcal/molHFCAdedeji, Connor, et al., 1978MS

Tungsten hexacarbonyl (cr) + 31,3-Diazine (g) = C18H15N3O3W (g) + 3Carbon monoxide (g)

By formula: C6O6W (cr) + 3C4H4N2 (g) = C18H15N3O3W (g) + 3CO (g)

Quantity Value Units Method Reference Comment
Deltar-13.1 ± 2.0kcal/molHFCAdedeji, Connor, et al., 1978MS

C10H5CrNO5 (cr) + Carbon monoxide (g) = Chromium hexacarbonyl (g) + 1,3-Diazine (g)

By formula: C10H5CrNO5 (cr) + CO (g) = C6CrO6 (g) + C4H4N2 (g)

Quantity Value Units Method Reference Comment
Deltar18. ± 1.kcal/molDSCDaamen, van der Poel, et al., 1979MS

C10H5MoNO5 (cr) + Carbon monoxide (g) = Molybdenum hexacarbonyl (g) + 1,3-Diazine (g)

By formula: C10H5MoNO5 (cr) + CO (g) = C6MoO6 (g) + C4H4N2 (g)

Quantity Value Units Method Reference Comment
Deltar14. ± 0.7kcal/molDSCDaamen, van der Poel, et al., 1979MS

Iron ion (1+) + 1,3-Diazine = (Iron ion (1+) bullet 1,3-Diazine)

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

Quantity Value Units Method Reference Comment
Deltar47.5 ± 1.9kcal/molCIDTAmunugama and Rodgers, 2001RCD

Chromium ion (1+) + 1,3-Diazine = (Chromium ion (1+) bullet 1,3-Diazine)

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

Quantity Value Units Method Reference Comment
Deltar42.4 ± 1.5kcal/molCIDTAmunugama and Rodgers, 2001RCD

Titanium ion (1+) + 1,3-Diazine = (Titanium ion (1+) bullet 1,3-Diazine)

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

Quantity Value Units Method Reference Comment
Deltar51.1 ± 2.5kcal/molCIDTAmunugama and Rodgers, 2001RCD

Manganese ion (1+) + 1,3-Diazine = (Manganese ion (1+) bullet 1,3-Diazine)

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

Quantity Value Units Method Reference Comment
Deltar38.0 ± 2.3kcal/molCIDTAmunugama and Rodgers, 2001RCD

Scandium ion (1+) + 1,3-Diazine = (Scandium ion (1+) bullet 1,3-Diazine)

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

Quantity Value Units Method Reference Comment
Deltar51.2 ± 2.2kcal/molCIDTAmunugama and Rodgers, 2001RCD

Magnesium ion (1+) + 1,3-Diazine = (Magnesium ion (1+) bullet 1,3-Diazine)

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

Quantity Value Units Method Reference Comment
Deltar41.5 ± 1.4kcal/molCIDTAmunugama and Rodgers, 2001RCD

Vanadium ion (1+) + 1,3-Diazine = (Vanadium ion (1+) bullet 1,3-Diazine)

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

Quantity Value Units Method Reference Comment
Deltar48.8 ± 1.7kcal/molCIDTAmunugama and Rodgers, 2001RCD

Nickel ion (1+) + 1,3-Diazine = (Nickel ion (1+) bullet 1,3-Diazine)

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

Quantity Value Units Method Reference Comment
Deltar58.3 ± 2.3kcal/molCIDTAmunugama and Rodgers, 2001RCD

Aluminum ion (1+) + 1,3-Diazine = (Aluminum ion (1+) bullet 1,3-Diazine)

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

Quantity Value Units Method Reference Comment
Deltar38.0 ± 1.4kcal/molCIDTAmunugama and Rodgers, 2001RCD

Zinc ion (1+) + 1,3-Diazine = (Zinc ion (1+) bullet 1,3-Diazine)

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

Quantity Value Units Method Reference Comment
Deltar49.8 ± 1.8kcal/molCIDTAmunugama and Rodgers, 2001RCD

Cobalt ion (1+) + 1,3-Diazine = (Cobalt ion (1+) bullet 1,3-Diazine)

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

Quantity Value Units Method Reference Comment
Deltar58.6 ± 3.2kcal/molCIDTAmunugama and Rodgers, 2001RCD

Copper ion (1+) + 1,3-Diazine = (Copper ion (1+) bullet 1,3-Diazine)

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

Quantity Value Units Method Reference Comment
Deltar59.6 ± 2.3kcal/molCIDTAmunugama and Rodgers, 2001RCD

References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Reaction thermochemistry data, Notes

Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Nabavian, Sabbah, et al., 1977
Nabavian, P.M.; Sabbah, R.; Chastel, R.; Laffitte, M., Thermodynamique de composes azotes. II. Etude thermochimique des acides aminobenzoiques, de la pyrimidine, de l'uracile et de la thymine., J. Chim. Phys., 1977, 74, 115-126. [all data]

Pedley, Naylor, et al., 1986
Pedley, J.B.; Naylor, R.D.; Kirby, S.P., Thermochemical Data of Organic Compounds, Chapman and Hall, New York, 1986, 1-792. [all data]

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]

Cox and Pilcher, 1970
Cox, J.D.; Pilcher, G., Thermochemistry of Organic and Organometallic Compounds, Academic Press, New York, 1970, 1-636. [all data]

Wovkulich and Atwood, 1980
Wovkulich, M.J.; Atwood, J.D., J. Organometal. Chem., 1980, 184, 77. [all data]

Dennenberg and Darensbourg, 1972
Dennenberg, R.J.; Darensbourg, D.J., Inorg. Chem., 1972, 11, 72. [all data]

Graham and Angelici, 1967
Graham, J.R.; Angelici, R.J., Inorg. Chem., 1967, 6, 2082. [all data]

Nakashima and Adamson, 1982
Nakashima, M.; Adamson, A.W., J. Phys. Chem., 1982, 86, 2905. [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]

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]

Gonzalez, Zhang, et al., 1988
Gonzalez, A.A.; Zhang, K.; Nolan, S.P.; Lopez de la Vega, R.; Mukerjee, S.L.; Hoff, C.D., Organometallics, 1988, 7, 2429. [all data]

Adedeji, Connor, et al., 1978
Adedeji, F.A.; Connor, J.A.; Demain, C.P.; Martinho Simões, J.A.; Skinner, H.A.; Zafarani- Moattar, M.T., J. Organometal. Chem., 1978, 149, 333. [all data]

Nolan, Hoff, et al., 1985
Nolan, S.P.; Hoff, C.D.; Landrum, J.T., J. Organometal. Chem., 1985, 282, 357. [all data]

Le Barbu, Schiedt, et al., 2002
Le Barbu, K.; Schiedt, J.; Weinkauf, R.; Schlag, E.W.; Nilles, J.M.; Xu, S.J.; Thomas, O.C.; Bowen, K.H., Microsolvation of small anions by aromatic molecules: An exploratory study, J. Chem. Phys., 2002, 116, 22, 9663-9671, https://doi.org/10.1063/1.1475750 . [all data]

Mukerjee, Lang, et al., 1992
Mukerjee, S.L.; Lang, R.F.; Ju, T.; Kiss, G.; Hoff, C.D.; Nolan, S.P., Inorg. Chem., 1992, 31, 4885. [all data]

Partenheimer and Durham, 1974
Partenheimer, W.; Durham, B., J. Am. Chem. Soc., 1974, 96, 3800. [all data]

Daamen, van der Poel, et al., 1979
Daamen, H.; van der Poel, H.; Stufkens, D.J.; Oskam, A., Thermochim. Acta, 1979, 34, 69. [all data]

Meester, Vriends, et al., 1976
Meester, M.A.M.; Vriends, R.C.J.; Stufkens, D.J.; Vrieze, K., Inorg. Chim. Acta, 1976, 19, 95. [all data]

Yang, Vaida, et al., 1988
Yang, G.K.; Vaida, V.; Peters, K.S., Polyhedron, 1988, 7, 1619. [all data]

Zhang, Gonzalez, et al., 1991
Zhang, K.; Gonzalez, A.A.; Murkerjee, S.L.; Chou, S.-J.; Hoff, C.D.; Kubat- Martin, K.A.; Barnhart, D.; Kubas, G.J., J. Am. Chem. Soc., 1991, 113, 9170. [all data]

Amunugama and Rodgers, 2001
Amunugama, R.; Rodgers, M.T., Periodic Trends in the Binding of Metal Ions to Pyrimidine Studied by Threshold Collision-Induced Dissociation and Density Functional Theory, J. Phys. Chem. A, 2001, 105, 43, 9883, https://doi.org/10.1021/jp010663i . [all data]


Notes

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Reaction thermochemistry data, References