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Propyne

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

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

C3H3- + Hydrogen cation = Propyne

By formula: C3H3- + H+ = C3H4

Quantity Value Units Method Reference Comment
Deltar380.3 ± 2.1kcal/molG+TSGal, Decouzon, et al., 2001gas phase; B
Deltar381.8 ± 2.3kcal/molD-EARobinson, Polak, et al., 1995gas phase; B
Deltar381.1 ± 2.1kcal/molG+TSRobinson, Polak, et al., 1995gas phase; Relative to MeOH at 375.0. isomerization accounted for in kinetic scheme; B
Deltar381.0 ± 2.1kcal/molG+TSBartmess, Scott, et al., 1979gas phase; value altered from reference due to change in acidity scale; B
Quantity Value Units Method Reference Comment
Deltar372.6 ± 2.0kcal/molIMREGal, Decouzon, et al., 2001gas phase; B
Deltar373.4 ± 2.0kcal/molIMRERobinson, Polak, et al., 1995gas phase; Relative to MeOH at 375.0. isomerization accounted for in kinetic scheme; B
Deltar373.3 ± 2.0kcal/molIMREBartmess, Scott, et al., 1979gas phase; value altered from reference due to change in acidity scale; B

2Hydrogen + Propyne = Propane

By formula: 2H2 + C3H4 = C3H8

Quantity Value Units Method Reference Comment
Deltar-69.22 ± 0.15kcal/molChydConn, Kistiakowsky, et al., 1939gas phase; Reanalyzed by Cox and Pilcher, 1970, Original value = -69.03 ± 0.14 kcal/mol; At 355 K; ALS

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

By formula: Li+ + C3H4 = (Li+ bullet C3H4)

Quantity Value Units Method Reference Comment
Deltar28.5kcal/molICRStaley and Beauchamp, 1975gas phase; switching reaction(Li+)H2O, from graph; Dzidic and Kebarle, 1970 extrapolated; M

Allene = Propyne

By formula: C3H4 = C3H4

Quantity Value Units Method Reference Comment
Deltar-0.90 ± 0.50kcal/molCmCordes and Gunzler, 1959gas phase; Reanalyzed by Cox and Pilcher, 1970, Original value = -0.81 kcal/mol; ALS

Cobalt ion (1+) + Propyne = (Cobalt ion (1+) bullet Propyne)

By formula: Co+ + C3H4 = (Co+ bullet C3H4)

Enthalpy of reaction

DeltarH° (kcal/mol) T (K) Method Reference Comment
18.9 (+2.1,-0.) CIDHaynes and Armentrout, 1994gas phase; «DELTA»rH>=, guided ion beam CID; M

(CAS Reg. No. 65887-19-6 bullet 4294967295Propyne) + Propyne = CAS Reg. No. 65887-19-6

By formula: (CAS Reg. No. 65887-19-6 bullet 4294967295C3H4) + C3H4 = CAS Reg. No. 65887-19-6

Quantity Value Units Method Reference Comment
Deltar33.8 ± 2.1kcal/molN/ADePuy, Gronert, et al., 1989gas phase; B

References

Go To: Top, Reaction thermochemistry data, Notes

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

Gal, Decouzon, et al., 2001
Gal, J.F.; Decouzon, M.; Maria, P.C.; Gonzalez, A.I.; Mo, O.; Yanez, M.; El Chaouch, S.; Guillemin, J.C., Acidity trends in alpha,beta-unsaturated alkanes, silanes, germanes, and stannanes, J. Am. Chem. Soc., 2001, 123, 26, 6353-6359, https://doi.org/10.1021/ja004079j . [all data]

Robinson, Polak, et al., 1995
Robinson, M.S.; Polak, M.L.; Bierbaum, V.M.; DePuy, C.H.; Lineberger, W.C., Experimental Studies of Allene, Methylacetylene, and the Propargyl Radical: Bond Dissociation Energies, Gas-Phase Acidities, and Ion-Molecule Chemistry, J. Am. Chem. Soc., 1995, 117, 25, 6766, https://doi.org/10.1021/ja00130a017 . [all data]

Bartmess, Scott, et al., 1979
Bartmess, J.E.; Scott, J.A.; McIver, R.T., Jr., The gas phase acidity scale from methanol to phenol, J. Am. Chem. Soc., 1979, 101, 6047. [all data]

Conn, Kistiakowsky, et al., 1939
Conn, J.B.; Kistiakowsky, G.B.; Smith, E.A., Heats of organic reactions. VIII. Some further hydrogenations, including those of some acetylenes, J. Am. Chem. Soc., 1939, 61, 1868-1876. [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]

Staley and Beauchamp, 1975
Staley, R.H.; Beauchamp, J.L., Intrinsic Acid - Base Properties of Molecules. Binding Energies of Li+ to pi - and n - Donor Bases, J. Am. Chem. Soc., 1975, 97, 20, 5920, https://doi.org/10.1021/ja00853a050 . [all data]

Dzidic and Kebarle, 1970
Dzidic, I.; Kebarle, P., Hydration of the Alkali Ions in the Gas Phase. Enthalpies and Entropies of Reactions M+(H2O)n-1 + H2O = M+(H2O)n, J. Phys. Chem., 1970, 74, 7, 1466, https://doi.org/10.1021/j100702a013 . [all data]

Cordes and Gunzler, 1959
Cordes, J.F.; Gunzler, H., Das propin/propadien-gleichgewicht, Chem. Ber., 1959, 92, 1055-1062. [all data]

Haynes and Armentrout, 1994
Haynes, C.L.; Armentrout, P.B., Thermochemistry and Structures of CoC3H6+: Metallacyclic and Metal-Alkene Isomers, Organomettalics, 1994, 13, 9, 3480, https://doi.org/10.1021/om00021a022 . [all data]

DePuy, Gronert, et al., 1989
DePuy, C.H.; Gronert, S.; Barlow, S.E.; Bierbaum, V.M.; Damrauer, R., The Gas Phase Acidities of the Alkanes, J. Am. Chem. Soc., 1989, 111, 6, 1968, https://doi.org/10.1021/ja00188a003 . [all data]


Notes

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