Home Symbol which looks like a small house Up Solid circle with an upward pointer in it

3-Butenenitrile

Data at NIST subscription sites:

NIST subscription sites provide data under the NIST Standard Reference Data Program, but require an annual fee to access. The purpose of the fee is to recover costs associated with the development of data collections included in such sites. Your institution may already be a subscriber. Follow the links above to find out more about the data in these sites and their terms of usage.


Gas phase thermochemistry data

Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, IR Spectrum, Mass spectrum (electron ionization), References, Notes

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
Deltafgas37.70kcal/molCcbKonicek, Prochzka, et al., 1969 

Condensed phase thermochemistry data

Go To: Top, Gas phase thermochemistry data, Phase change data, Reaction thermochemistry data, IR Spectrum, Mass spectrum (electron ionization), References, Notes

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
Deltafliquid28.14kcal/molCcbKonicek, Prochzka, et al., 1969 
Quantity Value Units Method Reference Comment
Deltacliquid-575.14 ± 0.27kcal/molCcbKonicek, Prochzka, et al., 1969 
Deltacliquid-574.9kcal/molCcbBruylants and Christiaen, 1925 

Phase change data

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Reaction thermochemistry data, IR Spectrum, Mass spectrum (electron ionization), References, Notes

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
Deltavap9.582kcal/molN/AMajer and Svoboda, 1985 
Deltavap9.56kcal/molVKonicek, Prochzka, et al., 1969ALS
Deltavap9.56kcal/molN/AKonicek, Prochzka, et al., 1969DRB
Deltavap9.56kcal/molN/AKonicek, Prochzka, et al., 1969AC

Enthalpy of vaporization

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

Antoine Equation Parameters

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

View plot Requires a JavaScript / HTML 5 canvas capable browser.

Temperature (K) A B C Reference Comment
253.6 - 392.4.376821526.272-43.316Stull, 1947Coefficents calculated by NIST from author's data.

Reaction thermochemistry data

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, IR Spectrum, Mass spectrum (electron ionization), References, Notes

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
Deltar357.3 ± 3.0kcal/molG+TSLuna, Mo, et al., 2006gas phase; Acid CH3CH=CHCN. Between MeSH, EtSH
Deltar358.8 ± 3.1kcal/molG+TSChou, Dahlke, et al., 1993gas phase; Acid: CH2=CHCH2CN
Deltar363.5 ± 5.1kcal/molG+TSDahlke and Kass, 1991gas phase; Between MeCHO, HCONH2. Reprotonation site uncertain.
Quantity Value Units Method Reference Comment
Deltar349.9 ± 3.0kcal/molIMRBLuna, Mo, et al., 2006gas phase; Acid CH3CH=CHCN. Between MeSH, EtSH
Deltar351.7 ± 3.0kcal/molIMRBChou, Dahlke, et al., 1993gas phase; Acid: CH2=CHCH2CN
Deltar356.3 ± 5.0kcal/molIMRBDahlke and Kass, 1991gas phase; Between MeCHO, HCONH2. Reprotonation site uncertain.
Deltar<365.0 ± 2.0kcal/molIMRBDawson and Nibbering, 1980gas phase; Acid: CH2=CHCH2CN

IR Spectrum

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Mass spectrum (electron ionization), References, Notes

Data compiled by: Coblentz Society, Inc.

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


Mass spectrum (electron ionization)

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

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

Notice: This spectrum may be better viewed with a Javascript and HTML 5 enabled browser.

Mass spectrum
For Zoom
1.) Enter the desired X axis range (e.g., 100, 200)
2.) Check here for automatic Y scaling
3.) Press here to zoom

Additional Data

View image of digitized spectrum (can be printed in landscape orientation).

View spectrum image in SVG format.

Download spectrum in JCAMP-DX format.

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 ALPHA Chemicals / NIST MS Data Center.
NIST MS number 125374

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.


References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, IR Spectrum, Mass spectrum (electron ionization), 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

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, IR Spectrum, Mass spectrum (electron ionization), References