Propanedinitrile

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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
Δfgas266.3 ± 1.0kJ/molCcbBeckhaus, Dogan, et al., 1990 
Δfgas266. ± 2.kJ/molCcbBoyd, Guha, et al., 1967 

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
Δfsolid187.9 ± 0.2kJ/molCcbBeckhaus, Dogan, et al., 1990ALS
Δfsolid186. ± 1.kJ/molCcbBoyd, Guha, et al., 1967ALS
Quantity Value Units Method Reference Comment
Δcsolid-1654.2 ± 0.2kJ/molCcbBeckhaus, Dogan, et al., 1990ALS
Δcsolid-1653. ± 1.kJ/molCcbBoyd, Guha, et al., 1967ALS
Quantity Value Units Method Reference Comment
solid,1 bar130.96J/mol*KN/AGirdhar, Westrum, et al., 1968crystaline, I phase; Entropy as calculated from data on undercooled, c,I from 5 K and from data on c,II, c,II/c,I transition, and c,I is the same.; DH

Constant pressure heat capacity of solid

Cp,solid (J/mol*K) Temperature (K) Reference Comment
110.29298.15Girdhar, Westrum, et al., 1968crystaline, I phase; T = 5 to 320 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
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DRB - Donald R. Burgess, Jr.
AC - William E. Acree, Jr., James S. Chickos
DH - Eugene S. Domalski and Elizabeth D. Hearing

Quantity Value Units Method Reference Comment
Tboil493.2KN/AAldrich Chemical Company Inc., 1990BS
Tboil491.7KN/AWeast and Grasselli, 1989BS
Quantity Value Units Method Reference Comment
Tfus305.KN/AStephenson, 1994Uncertainty assigned by TRC = 2. K; TRC
Tfus304.KN/ATrunel, 1939Uncertainty assigned by TRC = 3. K; TRC
Tfus307.6KN/AVan de Vloed, 1939Uncertainty assigned by TRC = 0.6 K; TRC
Tfus304.65KN/ABruhl, 1895Uncertainty assigned by TRC = 1.5 K; TRC
Quantity Value Units Method Reference Comment
Ttriple304.910KN/AGirdhar, Westrum, et al., 1968, 2Crystal phase 1 phase; Uncertainty assigned by TRC = 0.06 K; TRC
Ttriple304.980KN/AGirdhar, Westrum, et al., 1968, 2Crystal phase 1 phase; Uncertainty assigned by TRC = 0.02 K; TRC
Ttriple304.99KN/AWestrum and Wulff, 1968Crystal phase 1 phase; Uncertainty assigned by TRC = 0.02 K; TRC
Quantity Value Units Method Reference Comment
Δsub78.37 ± 0.96kJ/molCBeckhaus, Dogan, et al., 1990ALS
Δsub78.4kJ/molN/ABeckhaus, Dogan, et al., 1990DRB
Δsub78.2 ± 1.0kJ/molN/ABeckhaus, Dogan, et al., 1990Based on data from 278. to 299. K.; AC
Δsub79.1 ± 0.8kJ/molVBoyd, Guha, et al., 1967ALS
Δsub80.0kJ/molN/ABoyd, Guha, et al., 1967DRB

Reduced pressure boiling point

Tboil (K) Pressure (bar) Reference Comment
382.20.027Weast and Grasselli, 1989BS

Enthalpy of fusion

ΔfusH (kJ/mol) Temperature (K) Method Reference Comment
10.7305.DSCBadea, Blanco, et al., 2007AC
10.8305.N/ADomalski and Hearing, 1996AC

Temperature of phase transition

Ttrs (K) Initial Phase Final Phase Reference Comment
140.crystaline, IV, Recrystaline, II, entrant phase transition; second orderWasiutynski, Olejarczyk, et al., 1987DH
303.crystaline, Icrystaline, I'Wasiutynski, Olejarczyk, et al., 1987First order transition.; DH
260.crystaline, IIIcrystaline, IIWasiutynski, Olejarczyk, et al., 1987Phase III is stable below 260 K.; DH
295.crystaline, IIcrystaline, IWasiutynski, Olejarczyk, et al., 1987Second order transition.; DH

Enthalpy of phase transition

ΔHtrs (kJ/mol) Temperature (K) Initial Phase Final Phase Reference Comment
10.795304.99crystaline, IliquidGirdhar, Westrum, et al., 1968DH

Entropy of phase transition

ΔStrs (J/mol*K) Temperature (K) Initial Phase Final Phase Reference Comment
35.39304.99crystaline, IliquidGirdhar, Westrum, et al., 1968DH

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
MS - José A. Martinho Simões
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

C3HN2- + Hydrogen cation = Propanedinitrile

By formula: C3HN2- + H+ = C3H2N2

Quantity Value Units Method Reference Comment
Δr1405. ± 8.8kJ/molG+TSFujio, McIver, et al., 1981gas phase; value altered from reference due to change in acidity scale; B
Δr1406. ± 11.kJ/molG+TSCumming and Kebarle, 1978gas phase; B
Quantity Value Units Method Reference Comment
Δr1373. ± 8.4kJ/molIMREFujio, McIver, et al., 1981gas phase; value altered from reference due to change in acidity scale; B
Δr1373. ± 8.4kJ/molIMRECumming and Kebarle, 1978gas phase; B
Δr1376. ± 8.4kJ/molIMRETaft, Abboud, et al., 1988gas phase; Revised: 91TAF; B

Propanedinitrile (solution) + C5H11BrMg (solution) = C3HBrMgN2 (solution) + Pentane (solution)

By formula: C3H2N2 (solution) + C5H11BrMg (solution) = C3HBrMgN2 (solution) + C5H12 (solution)

Quantity Value Units Method Reference Comment
Δr-203.3kJ/molRSCHolm, 1983solvent: Diethyl ether; MS

Iodide + Propanedinitrile = (Iodide • Propanedinitrile)

By formula: I- + C3H2N2 = (I- • C3H2N2)

Quantity Value Units Method Reference Comment
Δr79.1 ± 4.2kJ/molTDAsCaldwell, Masucci, et al., 1989gas phase; B,M

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
L - Sharon G. Lias

Data compiled as indicated in comments:
B - John E. Bartmess
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

Quantity Value Units Method Reference Comment
IE (evaluated)12.8 ± 0.1eVN/AN/AL
Quantity Value Units Method Reference Comment
Proton affinity (review)723.0kJ/molN/AHunter and Lias, 1998HL
Quantity Value Units Method Reference Comment
Gas basicity694.1kJ/molN/AHunter and Lias, 1998HL

Ionization energy determinations

IE (eV) Method Reference Comment
12.70PEMolder, Pikver, et al., 1983LBLHLM
12.88PEStafast and Bock, 1973LLK

De-protonation reactions

C3HN2- + Hydrogen cation = Propanedinitrile

By formula: C3HN2- + H+ = C3H2N2

Quantity Value Units Method Reference Comment
Δr1405. ± 8.8kJ/molG+TSFujio, McIver, et al., 1981gas phase; value altered from reference due to change in acidity scale; B
Δr1406. ± 11.kJ/molG+TSCumming and Kebarle, 1978gas phase; B
Quantity Value Units Method Reference Comment
Δr1373. ± 8.4kJ/molIMREFujio, McIver, et al., 1981gas phase; value altered from reference due to change in acidity scale; B
Δr1373. ± 8.4kJ/molIMRECumming and Kebarle, 1978gas phase; B
Δr1376. ± 8.4kJ/molIMRETaft, Abboud, et al., 1988gas phase; Revised: 91TAF; B

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 as indicated in comments:
B - John E. Bartmess
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. Searches may be limited to ion clustering reactions. A general reaction search form is also available.

Clustering reactions

Iodide + Propanedinitrile = (Iodide • Propanedinitrile)

By formula: I- + C3H2N2 = (I- • C3H2N2)

Quantity Value Units Method Reference Comment
Δr79.1 ± 4.2kJ/molTDAsCaldwell, Masucci, et al., 1989gas phase; B,M

IR Spectrum

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Data compiled by: Coblentz Society, Inc.


Mass spectrum (electron ionization)

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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: NIST Mass Spectrometry Data Center, William E. Wallace, director

Spectrum

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Mass spectrum
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Additional Data

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Owner NIST Mass Spectrometry Data Center
Collection (C) 2014 copyright by the U.S. Secretary of Commerce
on behalf of the United States of America. All rights reserved.
Origin Japan AIST/NIMC Database- Spectrum MS-NW- 597
NIST MS number 229070

All mass spectra in this site (plus many more) are available from the NIST/EPA/NIH Mass Spectral Library. Please see the following for information about the library and its accompanying search program.


UV/Visible spectrum

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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: Victor Talrose, Alexander N. Yermakov, Alexy A. Usov, Antonina A. Goncharova, Axlexander N. Leskin, Natalia A. Messineva, Natalia V. Trusova, Margarita V. Efimkina

Spectrum

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UVVis spectrum
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Additional Data

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Source Schurz and Ullrich, 1959
Owner INEP CP RAS, NIST OSRD
Collection (C) 2007 copyright by the U.S. Secretary of Commerce
on behalf of the United States of America. All rights reserved.
Origin INSTITUTE OF ENERGY PROBLEMS OF CHEMICAL PHYSICS, RAS
Source reference RAS UV No. 12875
Instrument n.i.g.
Melting point 32
Boiling point 218.5

Vibrational and/or electronic energy levels

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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: Takehiko Shimanouchi

Symmetry:   C     Symmetry Number σ = 2


 Sym.   No   Approximate   Selected Freq.  Infrared   Raman   Comments 
 Species   type of mode   Value   Rating   Value  Phase  Value  Phase

a1 1 CH2 s-str 2935  C 2935 VS liq. 2929 liq.
a1 2 CN s-str 2275  C 2275 M liq. 2263 liq. SF9)
a1 3 CH2 scis 1395  C 1395 VS liq. 1386 liq.
a1 4 CC s-str 890  C 890 S liq. 892 liq.
a1 5 CCC deform 582  C 582 M liq. 574 liq.
a1 6 CCN bend 167  C 167 liq.
a2 7 CH2 twist 1220  C 1220 ia VW liq. 1214 liq.
a2 8 CCN bend 367  C 371 ia M liq. 367 liq. SF12)
b1 9 CN a-str 2275  C 2275 M liq. 2263 liq. SF2)
b1 10 CH2 wag 1318  C 1318 W liq. 1310 liq.
b1 11 CC a-str 982  C 982 S liq. 975 liq.
b1 12 CCN bend 366  C 366 S liq. 367 liq. SF8)
b2 13 CH2 a-str 2968  C 2968 VS liq. 2960 liq.
b2 14 CH2 rock 933  C 933 M liq.
b2 15 CCN bend 337  C 337 S liq.

Source: Shimanouchi, 1972

Notes

VSVery strong
SStrong
MMedium
WWeak
VWVery weak
iaInactive
SFCalculation shows that the frequency approximately equals that of the vibration indicated in the parentheses.
C3~6 cm-1 uncertainty

Gas Chromatography

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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: NIST Mass Spectrometry Data Center, William E. Wallace, director

Kovats' RI, non-polar column, isothermal

View large format table.

Column type Active phase Temperature (C) I Reference Comment
CapillarySE-33120.801.Juvancz, Cserháti, et al., 199410. m/0.20 mm/0.15 μm, H2

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, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, Vibrational and/or electronic energy levels, Gas Chromatography, Notes

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

Beckhaus, Dogan, et al., 1990
Beckhaus, H.D.; Dogan, B.; Pakusch, J.; Verevkin, S.; Ruechardt, C., Geminal substituent effects. 4. The dependence of the inverse anomeric effect of geminal cyano groups on the structure, Chem. Ber., 1990, 123, 2153-2159. [all data]

Boyd, Guha, et al., 1967
Boyd, R.H.; Guha, K.R.; Wuthrich, R., Thermochemistry of cyanocarbons. II. The heats of combustion of pyridinium dicyanomethylide, malononitrile, and fumaronitrile, J. Phys. Chem., 1967, 71, 2187-2191. [all data]

Girdhar, Westrum, et al., 1968
Girdhar, H.L.; Westrum, E.F., Jr.; Wulff, C.A., Thermodynamic properties and third-law cycle for malononitrile, J. Chem. Eng. Data, 1968, 13, 239-242. [all data]

Aldrich Chemical Company Inc., 1990
Aldrich Chemical Company Inc., Catalog Handbook of Fine Chemicals, Aldrich Chemical Company, Inc., Milwaukee WI, 1990, 1. [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]

Stephenson, 1994
Stephenson, R.M., Mutual Solubility of Water and Nitriles, J. Chem. Eng. Data, 1994, 39, 225-7. [all data]

Trunel, 1939
Trunel, P., Electric Moments in Several Homologous Series of Organic Compounds, Ann. Chim. (Paris), 1939, 12, 110. [all data]

Van de Vloed, 1939
Van de Vloed, A., Bull. Soc. Chim. Belg., 1939, 48, 229. [all data]

Bruhl, 1895
Bruhl, J.W., Spectrochemistry of Nitrogen-Containing Compounds. I., Z. Phys. Chem., Stoechiom. Verwandtschaftsl., 1895, 16, 193. [all data]

Girdhar, Westrum, et al., 1968, 2
Girdhar, H.L.; Westrum, E.F.; Wulff, C.A., Thermodynamic properties and third-law cycle for malononitrile., J. Chem. Eng. Data, 1968, 13, 239-42. [all data]

Westrum and Wulff, 1968
Westrum, E.F.; Wulff, C.A., Thermodynamic properties and third-law cycle for malononitrile, J. Chem. Eng. Data, 1968, 13, 239. [all data]

Badea, Blanco, et al., 2007
Badea, Elena; Blanco, Ignazio; Della Gatta, Giuseppe, Fusion and solid-to-solid transitions of a homologous series of alkane-α,ω-dinitriles, The Journal of Chemical Thermodynamics, 2007, 39, 10, 1392-1398, https://doi.org/10.1016/j.jct.2007.03.005 . [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]

Wasiutynski, Olejarczyk, et al., 1987
Wasiutynski, T.; Olejarczyk, W.; Sciesinski, J.; Witko, W., Phase transition studies of malononitrile, J. Phys. C: Solid State Phys., 1987, 20, L65-L69. [all data]

Fujio, McIver, et al., 1981
Fujio, M.; McIver, R.T., Jr.; Taft, R.W., Effects on the acidities of phenols from specific substituent-solvent interactions. Inherent substituent parameters from gas phase acidities, J. Am. Chem. Soc., 1981, 103, 4017. [all data]

Cumming and Kebarle, 1978
Cumming, J.B.; Kebarle, P., Summary of gas phase measurements involving acids AH. Entropy changes in proton transfer reactions involving negative ions. Bond dissociation energies D(A-H) and electron affinities EA(A), Can. J. Chem., 1978, 56, 1. [all data]

Taft, Abboud, et al., 1988
Taft, R.W.; Abboud, J.L.M.; Anvia, F.; Berthelot, M.; Fujio, M.; Gal, J.-F.; Headley, A.D.; Henderson, W.G., Regarding the Inherent Dependence of Resonance Effects of Strongly Conjugated Substituents on Electron Demand, J. Am. Chem. Soc., 1988, 110, 6, 1797, https://doi.org/10.1021/ja00214a023 . [all data]

Holm, 1983
Holm, T., Acta Chem. Scand. B, 1983, 37, 797. [all data]

Caldwell, Masucci, et al., 1989
Caldwell, G.W.; Masucci, J.A.; Ikonomou, M.G., Negative Ion Chemical Ionization Mass Spectrometry - Binding of Molecules to Bromide and Iodide Anions, Org. Mass Spectrom., 1989, 24, 1, 8, https://doi.org/10.1002/oms.1210240103 . [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]

Molder, Pikver, et al., 1983
Molder, U.H.; Pikver, R.J.; Koppel, I.A., Photoelectron spectra of molecules. 3. Nitriles, Org. React. Tartu, 1983, 20, 230. [all data]

Stafast and Bock, 1973
Stafast, H.; Bock, H., Photoelectron spectra molecular properties. XVII. Hyperconjugation in dicyanomethane and 2,2-dicyano propane, Z. Naturforsch. B:, 1973, 28, 746. [all data]

Schurz and Ullrich, 1959
Schurz, J.; Ullrich, A., Z. physik. Chem. (Frankfurt), 1959, 21, 185. [all data]

Shimanouchi, 1972
Shimanouchi, T., Tables of Molecular Vibrational Frequencies Consolidated Volume I, National Bureau of Standards, 1972, 1-160. [all data]

Juvancz, Cserháti, et al., 1994
Juvancz, Z.; Cserháti, T.; Markides, K.E.; Bradshaw, J.S.; Lee, M.L., Characterization of some new polysiloxane stationary phases by principal component analysis, Chromatographia, 1994, 38, 3/4, 227-231, https://doi.org/10.1007/BF02290341 . [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, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, Vibrational and/or electronic energy levels, Gas Chromatography, References