Isobutyronitrile

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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
Δfgas22.8kJ/molCcrHall and Baldt, 1971 
Δfgas24.3 ± 1.8kJ/molCcbEvans and Skinner, 1959Reanalyzed by Cox and Pilcher, 1970, Original value = 23. kJ/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 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
Δfliquid-13.8kJ/molCcrHall and Baldt, 1971ALS
Δfliquid-12.2 ± 0.84kJ/molCcbEvans and Skinner, 1959ALS
Quantity Value Units Method Reference Comment
Δcliquid-2560.6 ± 1.3kJ/molCcrHall and Baldt, 1971ALS
Δcliquid-2562.3 ± 0.75kJ/molCcbEvans and Skinner, 1959ALS

Constant pressure heat capacity of liquid

Cp,liquid (J/mol*K) Temperature (K) Reference Comment
156.2297.Hall and Baldt, 1971DH

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

Quantity Value Units Method Reference Comment
Tboil378. ± 5.KAVGN/AAverage of 19 values; Individual data points
Quantity Value Units Method Reference Comment
Tfus201.65KN/ATimmermans, 1952Uncertainty assigned by TRC = 0.5 K; TRC
Tfus201.65KN/ATimmermans and Delcourt, 1934Uncertainty assigned by TRC = 0.5 K; TRC
Quantity Value Units Method Reference Comment
Δvap37.22kJ/molN/AMajer and Svoboda, 1985 
Δvap36.7kJ/molVHall and Baldt, 1971ALS
Δvap36.6kJ/molN/AHall and Baldt, 1971DRB
Δvap37.13 ± 0.02kJ/molVHoward and Wadso, 1970ALS
Δvap36.5kJ/molN/AEvans and Skinner, 1959DRB

Enthalpy of vaporization

ΔvapH (kJ/mol) Temperature (K) Method Reference Comment
32.39377.N/AMajer and Svoboda, 1985 
35.9339.N/ASukhova, Vlasov, et al., 1979Based on data from 324. to 354. K.; AC
37.5321.BGBaldt and Hall, 1971Based on data from 303. to 352. K.; AC

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 by: John E. Bartmess

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

C4H6N- + Hydrogen cation = Isobutyronitrile

By formula: C4H6N- + H+ = C4H7N

Quantity Value Units Method Reference Comment
Δr1569. ± 9.2kJ/molG+TSBartmess, Scott, et al., 1979gas phase; value altered from reference due to change in acidity scale
Quantity Value Units Method Reference Comment
Δr1539. ± 8.4kJ/molIMREBartmess, Scott, et al., 1979gas phase; value altered from reference due to change in acidity scale

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:
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
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron

Quantity Value Units Method Reference Comment
Proton affinity (review)803.6kJ/molN/AHunter and Lias, 1998HL
Quantity Value Units Method Reference Comment
Gas basicity772.8kJ/molN/AHunter and Lias, 1998HL

Electron affinity determinations

EA (eV) Reference Comment
0.011710 ± 0.000087Hammer, Diri, et al., 2003B

Ionization energy determinations

IE (eV) Method Reference Comment
11.3PEOhno, Matumoto, et al., 1984LBLHLM
11.74PEOhno, Matumoto, et al., 1984Vertical value; LBLHLM
11.74PEKimura, Katsumata, et al., 1981Vertical value; LLK

Appearance energy determinations

Ion AE (eV) Other Products MethodReferenceComment
C2H4N+12.70?EIHeerma and deRidder, 1970RDSH
C3H4N+13.25?EIHeerma and deRidder, 1970RDSH
C3H6+12.25?EIHeerma and deRidder, 1970RDSH
C4H6N+12.55HEIHeerma and deRidder, 1970RDSH

De-protonation reactions

C4H6N- + Hydrogen cation = Isobutyronitrile

By formula: C4H6N- + H+ = C4H7N

Quantity Value Units Method Reference Comment
Δr1569. ± 9.2kJ/molG+TSBartmess, Scott, et al., 1979gas phase; value altered from reference due to change in acidity scale; B
Quantity Value Units Method Reference Comment
Δr1539. ± 8.4kJ/molIMREBartmess, Scott, et al., 1979gas phase; value altered from reference due to change in acidity scale; B

References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, 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.

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]

Evans and Skinner, 1959
Evans, F.W.; Skinner, H.A., The heats of combustion of organic compounds of nitrogen Part 2.-n-Propyl, isopropyl and phenyl cyandies, Trans. Faraday Soc., 1959, 55, 255-259. [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]

Timmermans, 1952
Timmermans, J., Freezing points of organic compounds. VVI New determinations., Bull. Soc. Chim. Belg., 1952, 61, 393. [all data]

Timmermans and Delcourt, 1934
Timmermans, J.; Delcourt, Y., Work of the International Bureau of Physico-Chemical Standards.VI. Physical Constants of Twenty Organic Compounds., J. Chim. Phys. Phys.-Chim. Biol., 1934, 31, 85-121. [all data]

Majer and Svoboda, 1985
Majer, V.; Svoboda, V., Enthalpies of Vaporization of Organic Compounds: A Critical Review and Data Compilation, Blackwell Scientific Publications, Oxford, 1985, 300. [all data]

Howard and Wadso, 1970
Howard, P.B.; Wadso, I., Enthalpies of vaporization of organic compounds IV. Alkyl Nitriles, Acta Chem. Scand., 1970, 24, 145. [all data]

Sukhova, Vlasov, et al., 1979
Sukhova, S.I.; Vlasov, O.N.; Li, L.V., Nov. Khim. Sredstva Azsch Rast., 1979, 51. [all data]

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

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]

Hammer, Diri, et al., 2003
Hammer, N.I.; Diri, K.; Jordan, K.D.; Desfrancois, C.; Compton, R.N., Dipole-bound anions of carbonyl, nitrile, and sulfoxide containing molecules, J. Chem. Phys., 2003, 119, 7, 3650-3660, https://doi.org/10.1063/1.1590959 . [all data]

Ohno, Matumoto, et al., 1984
Ohno, K.; Matumoto, S.; Imai, K.; Haraa, Y., Penning ionization electron spectroscopy of nitriles, J. Phys. Chem., 1984, 88, 206. [all data]

Kimura, Katsumata, et al., 1981
Kimura, K.; Katsumata, S.; Achiba, Y.; Yamazaki, T.; Iwata, S., Ionization energies, Ab initio assignments, and valence electronic structure for 200 molecules in Handbook of HeI Photoelectron Spectra of Fundamental Organic Compounds, Japan Scientific Soc. Press, Tokyo, 1981. [all data]

Heerma and deRidder, 1970
Heerma, W.; deRidder, J.J., The electron-impact induced fragmentation of some alkyl isocyanides and alpha-branched alkyl cyanides, Org. Mass Spectrom., 1970, 3, 1439. [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, References