3-Butenenitrile
- Formula: C4H5N
- Molecular weight: 67.0892
- IUPAC Standard InChIKey: SJNALLRHIVGIBI-UHFFFAOYSA-N
- CAS Registry Number: 109-75-1
- Chemical structure:
This structure is also available as a 2d Mol file or as a computed 3d SD file
The 3d structure may be viewed using Java or Javascript. - Other names: β-Butenonitrile; Allyl cyanide; Allylnitrile; Propene-3-nitrile; Vinylacetonitrile; 1-Butene-4-nitrile; 3-Butenonitrile; 3-Butenylnitrile; 3-Cyano-1-propene; 3-Cyanopropene; CH2=CHCH2CN; Acetonitrile, vinyl-; TL 350; Allylkyanid; NSC 2583; but-3-enenitrile
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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 |
---|---|---|---|---|---|
ΔfH°gas | 157.7 | kJ/mol | Ccb | Konicek, 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 |
---|---|---|---|---|---|
ΔfH°liquid | 117.7 | kJ/mol | Ccb | Konicek, Prochzka, et al., 1969 | |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°liquid | -2406.4 ± 1.1 | kJ/mol | Ccb | Konicek, Prochzka, et al., 1969 | |
ΔcH°liquid | -2405. | kJ/mol | Ccb | Bruylants 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 |
---|---|---|---|---|---|
Tboil | 392.2 | K | N/A | Weast and Grasselli, 1989 | BS |
Tboil | 391. | K | N/A | American Tokyo Kasei, 1988 | BS |
Tboil | 391.7 | K | N/A | Majer and Svoboda, 1985 | |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 40.09 | kJ/mol | N/A | Majer and Svoboda, 1985 | |
ΔvapH° | 40.0 | kJ/mol | V | Konicek, Prochzka, et al., 1969 | ALS |
ΔvapH° | 40.0 | kJ/mol | N/A | Konicek, Prochzka, et al., 1969 | DRB |
ΔvapH° | 40.0 | kJ/mol | N/A | Konicek, Prochzka, et al., 1969 | AC |
Enthalpy of vaporization
ΔvapH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
34.26 | 391.7 | N/A | Majer and Svoboda, 1985 | |
40.3 | 308. | A | Stephenson and Malanowski, 1987 | Based on data from 293. to 417. K.; AC |
41.6 | 268. | N/A | Stull, 1947 | Based on data from 254. to 392. K.; AC |
Antoine Equation Parameters
log10(P) = A − (B / (T + C))
P = vapor pressure (bar)
T = temperature (K)
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Temperature (K) | A | B | C | Reference | Comment |
---|---|---|---|---|---|
253.6 to 392. | 4.38253 | 1526.272 | -43.316 | Stull, 1947 | Coefficents 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- + =
By formula: C4H4N- + H+ = C4H5N
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 1495. ± 13. | kJ/mol | G+TS | Luna, Mo, et al., 2006 | gas phase; Acid CH3CH=CHCN. Between MeSH, EtSH |
ΔrH° | 1501. ± 13. | kJ/mol | G+TS | Chou, Dahlke, et al., 1993 | gas phase; Acid: CH2=CHCH2CN |
ΔrH° | 1521. ± 21. | kJ/mol | G+TS | Dahlke and Kass, 1991 | gas phase; Between MeCHO, HCONH2. Reprotonation site uncertain. |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 1464. ± 13. | kJ/mol | IMRB | Luna, Mo, et al., 2006 | gas phase; Acid CH3CH=CHCN. Between MeSH, EtSH |
ΔrG° | 1472. ± 13. | kJ/mol | IMRB | Chou, Dahlke, et al., 1993 | gas phase; Acid: CH2=CHCH2CN |
ΔrG° | 1491. ± 21. | kJ/mol | IMRB | Dahlke and Kass, 1991 | gas phase; Between MeCHO, HCONH2. Reprotonation site uncertain. |
ΔrG° | <1527. ± 8.4 | kJ/mol | IMRB | Dawson and Nibbering, 1980 | gas phase; Acid: CH2=CHCH2CN |
IR Spectrum
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Data compiled by: Coblentz Society, Inc.
- SOLID (KBr DISC); PERKIN-ELMER 180 (GRATING); DIGITIZED BY NIST FROM HARD COPY (FROM TWO SEGMENTS); 4 cm-1 resolution
- SOLUTION (10% CCl4 FOR 5000-1330, 10% CS2 FOR 1330-625 CM-1); Not specified, most likely a prism, grating, or hybrid spectrometer.; DIGITIZED BY NIST FROM HARD COPY; 4 cm-1 resolution
Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director
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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Additional Data
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Due to licensing restrictions, this spectrum cannot be downloaded.
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 |
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.
Spectrum
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Additional Data
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Source | Perkampus and Braunschweig, 1966 |
---|---|
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. 19920 |
Instrument | ZeissPMQ II |
Boiling point | 116-120 |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, 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]
Perkampus and Braunschweig, 1966
Perkampus, H.-H.; Braunschweig, T.H.,
UV atlas of organic compounds, 1966, 1, A1/13. [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), UV/Visible spectrum, References
- Symbols used in this document:
Tboil Boiling point ΔcH°liquid Enthalpy of combustion of liquid at standard conditions ΔfH°gas Enthalpy of formation of gas at standard conditions ΔfH°liquid Enthalpy of formation of liquid at standard conditions ΔrG° Free energy of reaction at standard conditions ΔrH° Enthalpy of reaction at standard conditions ΔvapH Enthalpy of vaporization ΔvapH° Enthalpy of vaporization at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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