2-Propenenitrile

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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 as indicated in comments:
DRB - Donald R. Burgess, Jr.
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Quantity Value Units Method Reference Comment
Δfgas41.25kcal/molN/ABaroody and Carpenter, 1972Value computed using ΔfHliquid° value of 140.0 kj/mol from Baroody and Carpenter, 1972 and ΔvapH° value of 32.6 kj/mol from Hall and Baldt, 1971.; DRB
Δfgas42.95kcal/molCcrHall and Baldt, 1971ALS

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
Δfliquid33.5kcal/molCcbBaroody and Carpenter, 1972ALS
Δfliquid35.16kcal/molCcrHall and Baldt, 1971ALS
Quantity Value Units Method Reference Comment
Δcliquid-419.79 ± 0.10kcal/molCcrHall and Baldt, 1971ALS
Δcliquid-420.5 ± 0.7kcal/molCcbDavis and Wiedeman, 1945ALS
Quantity Value Units Method Reference Comment
liquid42.761cal/mol*KN/AFinke, Messerly, et al., 1972DH

Constant pressure heat capacity of liquid

Cp,liquid (cal/mol*K) Temperature (K) Reference Comment
23.6298.15Mirzaliev, Shakhuradov, et al., 1987T = 213 to 333 K. Unsmoothed experimental datum given as 1.898 kJ/kg*K at 293 K. Cp(liq) = 2.05105 + 0.00465503T/K + 1.34722x10-5T2/K2 kJ/kg*K (213 to 333 K). Note, second coefficient should be negative.; DH
25.999298.15Finke, Messerly, et al., 1972T = 12 to 350 K.; DH
25.50297.Hall and Baldt, 1971DH
27.0298.Davis and Wiedeman, 1945DH

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:
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
BS - Robert L. Brown and Stephen E. Stein
AC - William E. Acree, Jr., James S. Chickos
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DRB - Donald R. Burgess, Jr.
CAL - James S. Chickos, William E. Acree, Jr., Joel F. Liebman, Students of Chem 202 (Introduction to the Literature of Chemistry), University of Missouri -- St. Louis
DH - Eugene S. Domalski and Elizabeth D. Hearing

Quantity Value Units Method Reference Comment
Tboil351. ± 1.KAVGN/AAverage of 11 values; Individual data points
Quantity Value Units Method Reference Comment
Tfus189.47KN/AWitschonke, 1954Uncertainty assigned by TRC = 0.2 K; TRC
Tfus189.6KN/AWitschonke, 1954Uncertainty assigned by TRC = 0.1 K; TRC
Tfus191.KN/ATimmermans, 1922Uncertainty assigned by TRC = 2. K; TRC
Quantity Value Units Method Reference Comment
Ttriple189.63KN/AFinke, Messerly, et al., 1972, 2Crystal phase 1 phase; Uncertainty assigned by TRC = 0.01 K; TRC
Quantity Value Units Method Reference Comment
Tc540.KN/AWilson, Wilson, et al., 1996Uncertainty assigned by TRC = 2. K; TRC
Quantity Value Units Method Reference Comment
Pc45.99atmN/AWilson, Wilson, et al., 1996Uncertainty assigned by TRC = 0.20 atm; TRC
Quantity Value Units Method Reference Comment
Δvap7.55kcal/molAStephenson and Malanowski, 1987Based on data from 283. to 343. K.; AC
Δvap7.8kcal/molVHall and Baldt, 1971ALS
Δvap7.79kcal/molN/AHall and Baldt, 1971DRB
Δvap7.8kcal/molEDavis and Wiedeman, 1945ALS

Enthalpy of vaporization

ΔvapH (kcal/mol) Temperature (K) Method Reference Comment
8.03272.AStephenson and Malanowski, 1987Based on data from 257. to 352. K.; AC
7.86308.N/AGubkov, Fermor, et al., 1964Based on data from 293. to 343. K.; AC
8.48237.N/ASevrugova, Sokorskii, et al., 1964Based on data from 222. to 351. K.; AC
7.79273. to 353.N/ADavis and Wiedeman, 1945AC

Antoine Equation Parameters

log10(P) = A − (B / (T + C))
    P = vapor pressure (atm)
    T = temperature (K)

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Temperature (K) A B C Reference Comment
293. to 343.2.69036621.275-121.929Gubkov, Fermor, et al., 1964, 2Coefficents calculated by NIST from author's data.
222. to 351.4.060901255.939-41.853Sevrugova, Sokorskii, et al., 1964, 2Coefficents calculated by NIST from author's data.

Enthalpy of fusion

ΔfusH (kcal/mol) Temperature (K) Reference Comment
1.49189.6Domalski and Hearing, 1996AC

Entropy of fusion

ΔfusS (cal/mol*K) Temperature (K) Reference Comment
1.75162.5Domalski and Hearing, 1996CAL
7.849189.6

Enthalpy of phase transition

ΔHtrs (kcal/mol) Temperature (K) Initial Phase Final Phase Reference Comment
0.28401162.5crystaline, IIcrystaline, IFinke, Messerly, et al., 1972DH
1.4890189.63crystaline, IliquidFinke, Messerly, et al., 1972DH

Entropy of phase transition

ΔStrs (cal/mol*K) Temperature (K) Initial Phase Final Phase Reference Comment
1.75162.5crystaline, IIcrystaline, IFinke, Messerly, et al., 1972DH
7.851189.63crystaline, IliquidFinke, Messerly, et al., 1972DH

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
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

C3H2N- + Hydrogen cation = 2-Propenenitrile

By formula: C3H2N- + H+ = C3H3N

Quantity Value Units Method Reference Comment
Δr371.1 ± 2.2kcal/molG+TSBartmess, 1980gas phase; value altered from reference due to change in acidity scale; B
Δr364.3 ± 4.6kcal/molEIAEHeni and Illenberger, 1986gas phase; From CH2=CHCN. G3MP2B3 calculations indicate a dHacdi ca. 374 kcal/mol; B
Quantity Value Units Method Reference Comment
Δr365.3 ± 2.0kcal/molIMREBartmess, 1980gas phase; value altered from reference due to change in acidity scale; B

2-Propenenitrile + 1,3 Diphenylisobenzofuran = C23H17NO

By formula: C3H3N + C20H14O = C23H17NO

Quantity Value Units Method Reference Comment
Δr-21.kcal/molKinSamuilov, Nurullina, et al., 1983liquid phase; solvent: Dichloroethane; Unpublished results; ALS
Δr-20.9 ± 0.2kcal/molCmKiselev, Ustyugov, et al., 1977liquid phase; solvent: 1,2-Dichloroethane; ALS

(CAS Reg. No. 42117-12-4 • 42949672952-Propenenitrile) + 2-Propenenitrile = CAS Reg. No. 42117-12-4

By formula: (CAS Reg. No. 42117-12-4 • 4294967295C3H3N) + C3H3N = CAS Reg. No. 42117-12-4

Quantity Value Units Method Reference Comment
Δr57.1 ± 2.2kcal/molN/ABartmess, Scott, et al., 1979gas phase; value altered from reference due to change in acidity scale; B

C3H4N+ + 2-Propenenitrile = (C3H4N+ • 2-Propenenitrile)

By formula: C3H4N+ + C3H3N = (C3H4N+ • C3H3N)

Quantity Value Units Method Reference Comment
Δr30.7kcal/molPHPMSMeot-Ner (Mautner) and Sieck, 1991gas phase; M
Quantity Value Units Method Reference Comment
Δr29.3cal/mol*KPHPMSMeot-Ner (Mautner) and Sieck, 1991gas phase; M

Propanenitrile, 3,3'-thiobis- + 2Ammonia = 22-Propenenitrile + ammonium sulphide

By formula: C6H8N2S + 2H3N = 2C3H3N + ammonium sulphide

Quantity Value Units Method Reference Comment
Δr30.20 ± 0.60kcal/molCmGladstone and Chang, 1966liquid phase; Heat of formation derived by Cox and Pilcher, 1970; ALS

(CAS Reg. No. 180058-39-3 • 42949672952-Propenenitrile) + 2-Propenenitrile = CAS Reg. No. 180058-39-3

By formula: (CAS Reg. No. 180058-39-3 • 4294967295C3H3N) + C3H3N = CAS Reg. No. 180058-39-3

Quantity Value Units Method Reference Comment
Δr22.8 ± 2.4kcal/molN/ABartmess, 1980gas phase; B

22-Propenenitrile + ammonium sulphide = Propanenitrile, 3,3'-thiobis- + 2Ammonia

By formula: 2C3H3N + ammonium sulphide = C6H8N2S + 2H3N

Quantity Value Units Method Reference Comment
Δr-30.20 ± 0.60kcal/molCmGladstone and Chang, 1966liquid phase; ALS

Henry's Law 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: Rolf Sander

Henry's Law constant (water solution)

kH(T) = H exp(d(ln(kH))/d(1/T) ((1/T) - 1/(298.15 K)))
H = Henry's law constant for solubility in water at 298.15 K (mol/(kg*bar))
d(ln(kH))/d(1/T) = Temperature dependence constant (K)

H (mol/(kg*bar)) d(ln(kH))/d(1/T) (K) Method Reference
7.2 XN/A
11.2800.XN/A

References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Henry's Law data, Notes

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

Baroody and Carpenter, 1972
Baroody, E.E.; Carpenter, G.A., Heats of formation of propellant compounds (U), Rpt. Naval Ordnance Systems Command Task No. 331-003/067-1/UR2402-001 for Naval Ordance Station, Indian Head, MD, 1972, 1-9. [all data]

Hall and Baldt, 1971
Hall, H.K., Jr.; Baldt, J.H., Thermochemistry of strained-ring bridgehead nitriles and esters, J. Am. Chem. Soc., 1971, 93, 140-145. [all data]

Davis and Wiedeman, 1945
Davis, H.S.; Wiedeman, O.F., Physical properties of acrylonitrile, Ind. Chim. Belge, 1945, 37, 482-485. [all data]

Finke, Messerly, et al., 1972
Finke, H.L.; Messerly, J.F.; Todd, S.S., Thermodynamic properties of acrylonitrile, 1-aminopropane, 2-aminopropane, and 2-methyl-2-aminopropane, J. Chem. Thermodynam., 1972, 4, 359-374. [all data]

Mirzaliev, Shakhuradov, et al., 1987
Mirzaliev, A.A.; Shakhuradov, Sh.G.; Guseinov, S.O., Investigation of the isobaric heat capacity of nitriles at different temperatures, Izv. Vyssh. Ucheb. Zaved., Neft i Gaz, 1987, 30(4), 55-58. [all data]

Witschonke, 1954
Witschonke, C.R., Freezing point and purity data for some organic compounds, Anal. Chem., 1954, 26, 562-4. [all data]

Timmermans, 1922
Timmermans, J., Investigation of the Freezing Point of Organic Substances VII, Bull. Soc. Chim. Belg., 1922, 31, 389. [all data]

Finke, Messerly, et al., 1972, 2
Finke, H.L.; Messerly, J.F.; Todd, S.S., Thermodynamic properties of acrylonitrile, 1-aminopropane, 2-aminopropane, and 2-methyl-2-aminopropane, J. Chem. Thermodyn., 1972, 4, 359. [all data]

Wilson, Wilson, et al., 1996
Wilson, L.C.; Wilson, H.L.; Wilding, W.V.; Wilson, G.M., Critical Point Measurements for Fourteen Compounds by a Static Method and a Flow Method, J. Chem. Eng. Data, 1996, 41, 1252-4. [all data]

Stephenson and Malanowski, 1987
Stephenson, Richard M.; Malanowski, Stanislaw, Handbook of the Thermodynamics of Organic Compounds, 1987, https://doi.org/10.1007/978-94-009-3173-2 . [all data]

Gubkov, Fermor, et al., 1964
Gubkov, A.N.; Fermor, N.A.; Smirnov, N.I., Zh. Prikl. Khim. (S.-Peterburg), 1964, 37, 2204. [all data]

Sevrugova, Sokorskii, et al., 1964
Sevrugova, N.N.; Sokorskii, V.A.; Zhavoronkov, N.M., Zh. Prikl. Khim. (Leningrad), 1964, 37, 1989. [all data]

Gubkov, Fermor, et al., 1964, 2
Gubkov, A.N.; Fermor, N.A.; Smirnov, N.I., Vapor Pressure of Mono-Poly Systems, Zh. Prikl. Khim. (Leningrad), 1964, 37, 2204-2210. [all data]

Sevrugova, Sokorskii, et al., 1964, 2
Sevrugova, N.N.; Sokorskii, V.A.; Zhavoronkov, N.M., Phase of Equilibrium for Mixtures Acrylonitrile-Acetonitrile, Zh. Prikl. Khim. (Leningrad), 1964, 37, 9, 1989-1993. [all data]

Domalski and Hearing, 1996
Domalski, Eugene S.; Hearing, Elizabeth D., Heat Capacities and Entropies of Organic Compounds in the Condensed Phase. Volume III, J. Phys. Chem. Ref. Data, 1996, 25, 1, 1, https://doi.org/10.1063/1.555985 . [all data]

Bartmess, 1980
Bartmess, J.E., Solvent effects on ion-molecule reactions. Vinyl anions vs. conjugate addition, J. Am. Chem. Soc., 1980, 102, 2483. [all data]

Heni and Illenberger, 1986
Heni, M.; Illenberger, E., Electron attachment by saturated nitriles. Acrylonitrile (CH2H3CN), and benzonitrile (C6H5CN), Int. J. Mass Spectrom. Ion Phys., 1986, 73, 127. [all data]

Samuilov, Nurullina, et al., 1983
Samuilov, Ya.D.; Nurullina, R.L.; Konovalov, A.I., Thermochemical and kinetic study of the Diels-Alder reaction with ethylene and acetylene dienophiles, Zh. Org. Khim., 1983, 19, 1431-1435. [all data]

Kiselev, Ustyugov, et al., 1977
Kiselev, V.D.; Ustyugov, A.N.; Breus, I.P.; Konovalov, A.I., Kinetic and thermochemical study of the Diels-Alder reaction, Dokl. Phys. Chem. (Engl. Transl.), 1977, 234, 320-322, In original 1089. [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]

Meot-Ner (Mautner) and Sieck, 1991
Meot-Ner (Mautner), M.; Sieck, L.W., Proton affinity ladders from variable-temperature equilibrium measurements. 1. A reevaluation of the upper proton affinity range, J. Am. Chem. Soc., 1991, 113, 12, 4448, https://doi.org/10.1021/ja00012a012 . [all data]

Gladstone and Chang, 1966
Gladstone, S.; Chang, H.Y., Determination of the standard heat of formation of 3,3'-thiodipropionitrile, J. Chem. Eng. Data, 1966, 11, 238-239. [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]


Notes

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