3-Butenenitrile

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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
Δfgas37.70kcal/molCcbKonicek, Prochzka, et al., 1969 

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 by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Quantity Value Units Method Reference Comment
Δfliquid28.14kcal/molCcbKonicek, Prochzka, et al., 1969 
Quantity Value Units Method Reference Comment
Δcliquid-575.14 ± 0.27kcal/molCcbKonicek, Prochzka, et al., 1969 
Δcliquid-574.9kcal/molCcbBruylants and Christiaen, 1925 

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
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
Tboil392.2KN/AWeast and Grasselli, 1989BS
Tboil391.KN/AAmerican Tokyo Kasei, 1988BS
Tboil391.7KN/AMajer and Svoboda, 1985 
Quantity Value Units Method Reference Comment
Δvap9.582kcal/molN/AMajer and Svoboda, 1985 
Δvap9.56kcal/molVKonicek, Prochzka, et al., 1969ALS
Δvap9.56kcal/molN/AKonicek, Prochzka, et al., 1969DRB
Δvap9.56kcal/molN/AKonicek, Prochzka, et al., 1969AC

Enthalpy of vaporization

ΔvapH (kcal/mol) Temperature (K) Method Reference Comment
8.188391.7N/AMajer and Svoboda, 1985 
9.63308.AStephenson and Malanowski, 1987Based on data from 293. to 417. K.; AC
9.94268.N/AStull, 1947Based on data from 254. to 392. K.; AC

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
253.6 to 392.4.376821526.272-43.316Stull, 1947Coefficents calculated by NIST from author's data.

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

C4H4N- + Hydrogen cation = 3-Butenenitrile

By formula: C4H4N- + H+ = C4H5N

Quantity Value Units Method Reference Comment
Δr357.3 ± 3.0kcal/molG+TSLuna, Mo, et al., 2006gas phase; Acid CH3CH=CHCN. Between MeSH, EtSH
Δr358.8 ± 3.1kcal/molG+TSChou, Dahlke, et al., 1993gas phase; Acid: CH2=CHCH2CN
Δr363.5 ± 5.1kcal/molG+TSDahlke and Kass, 1991gas phase; Between MeCHO, HCONH2. Reprotonation site uncertain.
Quantity Value Units Method Reference Comment
Δr349.9 ± 3.0kcal/molIMRBLuna, Mo, et al., 2006gas phase; Acid CH3CH=CHCN. Between MeSH, EtSH
Δr351.7 ± 3.0kcal/molIMRBChou, Dahlke, et al., 1993gas phase; Acid: CH2=CHCH2CN
Δr356.3 ± 5.0kcal/molIMRBDahlke and Kass, 1991gas phase; Between MeCHO, HCONH2. Reprotonation site uncertain.
Δr<365.0 ± 2.0kcal/molIMRBDawson and Nibbering, 1980gas phase; Acid: CH2=CHCH2CN

References

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

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

Konicek, Prochzka, et al., 1969
Konicek, J.; Prochzka, M.; Krestanov, V.; Smisek, M., Thermochemie der nitrile I. Über die bildungswärmen aliphatischer nitrile, Collect. Czech. Chem. Commun., 1969, 34, 2249-2257. [all data]

Bruylants and Christiaen, 1925
Bruylants, P.; Christiaen, A., Thermochimie des Butenes-Nitriles, Bull. Soc. Chim. Belg., 1925, 34, 144-150. [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]

American Tokyo Kasei, 1988
American Tokyo Kasei, TCI American Organic Chemical 88/89 Catalog, American Tokyo Kasei, Portland, OR, 1988, 1610. [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]

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]

Stull, 1947
Stull, Daniel R., Vapor Pressure of Pure Substances. Organic and Inorganic Compounds, Ind. Eng. Chem., 1947, 39, 4, 517-540, https://doi.org/10.1021/ie50448a022 . [all data]

Luna, Mo, et al., 2006
Luna, A.; Mo, O.; Yanez, M.; Gal, J.F.; Maria, P.C.; Guillemin, J.C., Gas-phase protonation and deprotonation of acrylonitrile derivatives N equivalent to C-CH=CH-X (X=CH3, NH2, PH2, SiH3), Chem. Eur. J., 2006, 12, 36, 9254-9261, https://doi.org/10.1002/chem.200600154 . [all data]

Chou, Dahlke, et al., 1993
Chou, P.K.; Dahlke, G.D.; Kass, S.R., Unimolecular Rearrangements of Carbanions in the Gas Phase .2. Cyclopropyl Anions, J. Chem. Soc. Chem. Comm., 1993, 115, 1, 315, https://doi.org/10.1021/ja00054a045 . [all data]

Dahlke and Kass, 1991
Dahlke, G.D.; Kass, S.R., Substituent Effects in the Gas Phase - 1-Substituted Allyl Anions, J. Am. Chem. Soc., 1991, 113, 15, 5566, https://doi.org/10.1021/ja00015a008 . [all data]

Dawson and Nibbering, 1980
Dawson, J.H.J.; Nibbering, N.M.M., The gas phase anionic chemistry of saturated and unsaturated aliphatic nitriles, Int. J. Mass Spectrom. Ion Phys., 1980, 33, 3. [all data]


Notes

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