Glycerin

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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:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
M - Michael M. Meot-Ner (Mautner) and Sharon G. Lias

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Individual Reactions

Glycerin + Nitric acid = 1,2,3-Propanetriol, 1-nitrate + Water

By formula: C3H8O3 + HNO3 = C3H7NO5 + H2O

Quantity Value Units Method Reference Comment
Δr-4.5 ± 0.5kcal/molEqkKazakov, Kirpichev, et al., 1990liquid phase; Heat of Nitration; ALS
Δr-2.39kcal/molCmTsvetkov, Sopin, et al., 1986liquid phase; ALS

C3H9O3+ + Glycerin = (C3H9O3+ • Glycerin)

By formula: C3H9O3+ + C3H8O3 = (C3H9O3+ • C3H8O3)

Bond type: Hydrogen bonds of the type OH-O between organics

Free energy of reaction

ΔrG° (kcal/mol) T (K) Method Reference Comment
13.7500.PHPMSSunner, Kulatunga, et al., 1986gas phase; M

Glycerin + Nitric acid = Glycerol-2-nitrate + Water

By formula: C3H8O3 + HNO3 = C3H7NO5 + H2O

Quantity Value Units Method Reference Comment
Δr-2.5 ± 0.6kcal/molEqkKazakov, Kirpichev, et al., 1990liquid phase; Heat of nitration; ALS

Glycerin + 3Nitric acid = Nitroglycerin + 3Water

By formula: C3H8O3 + 3HNO3 = C3H5N3O9 + 3H2O

Quantity Value Units Method Reference Comment
Δr-8.7 ± 0.4kcal/molCmKazakov, Lagodzinskaya, et al., 1989liquid phase; ALS

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:
MM - Michael M. Meot-Ner (Mautner)

Quantity Value Units Method Reference Comment
Proton affinity (review)209.1kcal/molN/AHunter and Lias, 1998HL
Quantity Value Units Method Reference Comment
Gas basicity196.kcal/molN/AHunter and Lias, 1998HL

Proton affinity at 298K

Proton affinity (kcal/mol) Reference Comment
>200.9Bouchoux, Buisson, et al., 2003MM
>199.8Bouchoux, Buisson, et al., 2003MM
>202.8 ± 0.29Bouchoux, Buisson, et al., 2003MM

Gas basicity at 298K

Gas basicity (review) (kcal/mol) Reference Comment
193.6Bouchoux, Buisson, et al., 2003MM
192.5Bouchoux, Buisson, et al., 2003MM
195.7 ± 0.1Bouchoux, Buisson, et al., 2003MM

References

Go To: Top, 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.

Kazakov, Kirpichev, et al., 1990
Kazakov, A.I.; Kirpichev, E.P.; Lagodzinskaya, G.V.; Andrienko, L.P.; Yunda, N.G.; Korolev, A.M.; Rubstov, Yu.I.; Manelis, G.B.; Eremenko, L.T., Study of nitration equilibrium in the glycerin-aqueous nitric acid system. 2. Changes in ΔH and ΔS in the nitration reaction, Bull. Acad. Sci. USSR, Div. Chem. Sci., 1990, 1565-1570. [all data]

Tsvetkov, Sopin, et al., 1986
Tsvetkov, V.G.; Sopin, V.P.; Tsvetkova, L.Ya.; Marchenko, G.N., Enthalpy of reaction of nitric acid with some organic compounds, J. Gen. Chem. USSR, 1986, 56, 471-474. [all data]

Sunner, Kulatunga, et al., 1986
Sunner, J.A.; Kulatunga, R.; Kebarle, P., Fast Atom Bombardment Mass Spectrometry and Gas Phase Basicities, Anal. Chem., 1986, 58, 7, 1312, https://doi.org/10.1021/ac00298a010 . [all data]

Kazakov, Lagodzinskaya, et al., 1989
Kazakov, A.I.; Lagodzinskaya, E.P.; Kirpichev, E.P.; Andrienko, L.P.; Yunda, N.G.; Korolev, A.M.; Robtsov, Yu.I.; Manelis, G.V.; Eremenko, L.T., Thermodynamics of nitration of glycerol, Dokl. Phys. Chem. (Engl. Transl.), 1989, 305, 287-291. [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]

Bouchoux, Buisson, et al., 2003
Bouchoux, G.; Buisson, D.A.; Bourcier, S.; Sablier, M., Application of the kinetic method to bifunctional bases. ESI tandem quadrupole experiments, Int. J. Mass Spectrom., 2003, 228, 1035. [all data]


Notes

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