Isobutyronitrile
- Formula: C4H7N
- Molecular weight: 69.1051
- IUPAC Standard InChIKey: LRDFRRGEGBBSRN-UHFFFAOYSA-N
- CAS Registry Number: 78-82-0
- 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: Propanenitrile, 2-methyl-; Isopropyl cyanide; Isopropylnitrile; 1-Cyano-1-methylethane; 2-Cyanopropane; 2-Methylpropanenitrile; 2-Methylpropionitrile; iso-C3H7CN; Dimethylacetonitrile; Isopropylkyanid; UN 2284; α-Methylpropanenitrile; NSC 60536
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Reaction thermochemistry data
Go To: Top, Gas phase ion energetics data, 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
C4H6N- + =
By formula: C4H6N- + H+ = C4H7N
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 1569. ± 9.2 | kJ/mol | G+TS | Bartmess, Scott, et al., 1979 | gas phase; value altered from reference due to change in acidity scale |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 1539. ± 8.4 | kJ/mol | IMRE | Bartmess, Scott, et al., 1979 | gas phase; value altered from reference due to change in acidity scale |
Gas phase ion energetics data
Go To: Top, Reaction thermochemistry data, References, Notes
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) | 803.6 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
Quantity | Value | Units | Method | Reference | Comment |
Gas basicity | 772.8 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
Electron affinity determinations
EA (eV) | Reference | Comment |
---|---|---|
0.011710 ± 0.000087 | Hammer, Diri, et al., 2003 | B |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
11.3 | PE | Ohno, Matumoto, et al., 1984 | LBLHLM |
11.74 | PE | Ohno, Matumoto, et al., 1984 | Vertical value; LBLHLM |
11.74 | PE | Kimura, Katsumata, et al., 1981 | Vertical value; LLK |
Appearance energy determinations
Ion | AE (eV) | Other Products | Method | Reference | Comment |
---|---|---|---|---|---|
C2H4N+ | 12.70 | ? | EI | Heerma and deRidder, 1970 | RDSH |
C3H4N+ | 13.25 | ? | EI | Heerma and deRidder, 1970 | RDSH |
C3H6+ | 12.25 | ? | EI | Heerma and deRidder, 1970 | RDSH |
C4H6N+ | 12.55 | H | EI | Heerma and deRidder, 1970 | RDSH |
De-protonation reactions
C4H6N- + =
By formula: C4H6N- + H+ = C4H7N
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 1569. ± 9.2 | kJ/mol | G+TS | Bartmess, Scott, et al., 1979 | gas phase; value altered from reference due to change in acidity scale; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 1539. ± 8.4 | kJ/mol | IMRE | Bartmess, Scott, et al., 1979 | gas phase; value altered from reference due to change in acidity scale; B |
References
Go To: Top, 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.
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, Reaction thermochemistry data, Gas phase ion energetics data, References
- Symbols used in this document:
AE Appearance energy EA Electron affinity ΔrG° Free energy of reaction at standard conditions ΔrH° Enthalpy of reaction at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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