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
- Permanent link for this species. Use this link for bookmarking this species for future reference.
- Information on this page:
- Other data available:
- Data at other public NIST sites:
- Options:
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, Gas phase ion energetics data, IR Spectrum, Gas Chromatography, 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 |
---|---|---|---|---|---|
ΔfH°gas | 22.8 | kJ/mol | Ccr | Hall and Baldt, 1971 | |
ΔfH°gas | 24.3 ± 1.8 | kJ/mol | Ccb | Evans and Skinner, 1959 | Reanalyzed by Cox and Pilcher, 1970, Original value = 23. kJ/mol |
Condensed phase thermochemistry data
Go To: Top, Gas phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Gas Chromatography, 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:
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 |
---|---|---|---|---|---|
ΔfH°liquid | -13.8 | kJ/mol | Ccr | Hall and Baldt, 1971 | ALS |
ΔfH°liquid | -12.2 ± 0.84 | kJ/mol | Ccb | Evans and Skinner, 1959 | ALS |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°liquid | -2560.6 ± 1.3 | kJ/mol | Ccr | Hall and Baldt, 1971 | ALS |
ΔcH°liquid | -2562.3 ± 0.75 | kJ/mol | Ccb | Evans and Skinner, 1959 | ALS |
Constant pressure heat capacity of liquid
Cp,liquid (J/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
156.2 | 297. | Hall and Baldt, 1971 | DH |
Phase change data
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Gas Chromatography, 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
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 |
---|---|---|---|---|---|
Tboil | 378. ± 5. | K | AVG | N/A | Average of 19 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 201.65 | K | N/A | Timmermans, 1952 | Uncertainty assigned by TRC = 0.5 K; TRC |
Tfus | 201.65 | K | N/A | Timmermans and Delcourt, 1934 | Uncertainty assigned by TRC = 0.5 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 37.22 | kJ/mol | N/A | Majer and Svoboda, 1985 | |
ΔvapH° | 36.7 | kJ/mol | V | Hall and Baldt, 1971 | ALS |
ΔvapH° | 36.6 | kJ/mol | N/A | Hall and Baldt, 1971 | DRB |
ΔvapH° | 37.13 ± 0.02 | kJ/mol | V | Howard and Wadso, 1970 | ALS |
ΔvapH° | 36.5 | kJ/mol | N/A | Evans and Skinner, 1959 | DRB |
Enthalpy of vaporization
ΔvapH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
32.39 | 377. | N/A | Majer and Svoboda, 1985 | |
35.9 | 339. | N/A | Sukhova, Vlasov, et al., 1979 | Based on data from 324. to 354. K.; AC |
37.5 | 321. | BG | Baldt and Hall, 1971 | Based on data from 303. to 352. K.; AC |
Reaction thermochemistry data
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, IR Spectrum, Gas Chromatography, 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, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, IR Spectrum, Gas Chromatography, 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 |
IR Spectrum
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Gas Chromatography, 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
Gas Phase Spectrum
Notice: This spectrum may be better viewed with a Javascript and HTML 5 enabled browser.
Notice: Concentration information is not available for this spectrum and, therefore, molar absorptivity values cannot be derived.
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 Standard Reference Data Program Collection (C) 2018 copyright by the U.S. Secretary of Commerce on behalf of the United States of America. All rights reserved. |
---|---|
Origin | Sadtler Research Labs Under US-EPA Contract |
State | gas |
Gas Chromatography
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics 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
Kovats' RI, non-polar column, isothermal
Column type | Active phase | Temperature (C) | I | Reference | Comment |
---|---|---|---|---|---|
Capillary | BPX-5 | 30. | 638. | Aflalaye, Sternberg, et al., 1995 | 12. m/0.15 mm/0.25 μm, H2 |
Capillary | BPX-5 | 30. | 643. | Aflalaye, Sternberg, et al., 1995 | 12. m/0.15 mm/0.25 μm, H2 |
Capillary | CP Sil 5 CB | 20. | 594.4 | Do and Raulin, 1992 | 25. m/0.15 mm/2. μm, H2 |
Capillary | PoraPLOT Q | 100. | 592. | Do and Raulin, 1989 | 10. m/0.32 mm/10. μm, H2 |
Capillary | PoraPLOT Q | 160. | 590. | Do and Raulin, 1989 | 10. m/0.32 mm/10. μm, H2 |
Van Den Dool and Kratz RI, non-polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | DB-5 | 626. | Dallüge, van Stee, et al., 2002 | 30. m/0.25 mm/1. μm, He, 2.5 K/min; Tstart: 50. C; Tend: 200. C |
Van Den Dool and Kratz RI, polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | DB-Wax | 993. | Shimoda, Peralta, et al., 1996 | 60. m/0.25 mm/0.25 μm, He, 3. K/min; Tstart: 50. C; Tend: 230. C |
Van Den Dool and Kratz RI, polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | DB-Wax | 1009. | Radovic, Careri, et al., 2001 | 30. m/0.25 mm/0.25 μm; Program: 30C(8min) => 4C/min => 60C => 6C/min => 160C => 20C/min => 200C(1min) |
Normal alkane RI, non-polar column, isothermal
Column type | Active phase | Temperature (C) | I | Reference | Comment |
---|---|---|---|---|---|
Capillary | OV-101 | 32. | 600. | Blazso, Ujszaszi, et al., 1980 | Column length: 20. m; Column diameter: 0.23 mm |
Normal alkane RI, non-polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | SPB-5 | 623. | Sivadier, Ratel, et al., 2009 | 60. m/0.32 mm/1.00 μm, 40. C @ 5. min, 3. K/min, 230. C @ 10. min |
Capillary | SPB-5 | 623. | Vasta, Ratel, et al., 2007 | 60. m/0.32 mm/1. μm, 40. C @ 5. min, 3. K/min, 230. C @ 5. min |
Capillary | HP-5 | 637.2 | Leffingwell and Alford, 2005 | 60. m/0.32 mm/0.25 μm, He, 30. C @ 2. min, 2. K/min, 260. C @ 28. min |
Normal alkane RI, polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | Supelcowax 10 | 1010. | Soria, Martinez-Castro, et al., 2008 | 50. m/0.25 mm/0.25 μm, Helium; Program: 45 0C (15 min) 3 0C/min -> 75 0C 5 0C/min -> 180 0C (10 min) |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Gas Chromatography, 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]
Aflalaye, Sternberg, et al., 1995
Aflalaye, A.; Sternberg, R.; Raulin, F.; Vidal-Madjar, C.,
Gas chromatography of Titan's atmosphere. VI. Analysis of low-molecular-mass hydrocarbons and nitriles with BPX5 capillary columns,
J. Chromatogr. A, 1995, 708, 2, 283-291, https://doi.org/10.1016/0021-9673(95)00410-O
. [all data]
Do and Raulin, 1992
Do, L.; Raulin, F.,
Gas chromatography of Titan's atmosphere. III. Analysis of low-molecular-weight hydrocarbons and nitriles with a CP-Sil-5 CB WCOT capillary column,
J. Chromatogr., 1992, 591, 1-2, 297-301, https://doi.org/10.1016/0021-9673(92)80247-R
. [all data]
Do and Raulin, 1989
Do, L.; Raulin, F.,
Gas chromatography of Titan's atmosphere. I. Analysis of low-molecular-weight hydrocarbons and nitriles with a PoraPLOT Q porous polymer coated open-tubular capillary column,
J. Chromatogr., 1989, 481, 45-54, https://doi.org/10.1016/S0021-9673(01)96751-2
. [all data]
Dallüge, van Stee, et al., 2002
Dallüge, J.; van Stee, L.L.P.; Xu, X.; Williams, J.; Beens, J.; Vreuls, R.J.J.; Brinkman, U.A.Th.,
Unravelling the composition of very complex samples by comprehensive gas chromatography coupled to time-of-flight mass spectrometry. Cigarette smoke,
J. Chromatogr. A, 2002, 974, 1-2, 169-184, https://doi.org/10.1016/S0021-9673(02)01384-5
. [all data]
Shimoda, Peralta, et al., 1996
Shimoda, M.; Peralta, R.R.; Osajima, Y.,
Headspace gas analysis of fish sauce,
J. Agric. Food Chem., 1996, 44, 11, 3601-3605, https://doi.org/10.1021/jf960345u
. [all data]
Radovic, Careri, et al., 2001
Radovic, B.S.; Careri, M.; Mangia, A.; Musci, M.; Gerboles, M.; Anklam, E.,
Analytical, nutritional, and clinical methods section. Contribution of dynamic headspace GC-MS analysis of aroma compounds to authenticity testing of honey,
Food Chem., 2001, 72, 4, 511-520, https://doi.org/10.1016/S0308-8146(00)00263-6
. [all data]
Blazso, Ujszaszi, et al., 1980
Blazso, M.; Ujszaszi, K.; Jakab, E.,
Isomeric structure of styrene-acrylonitrile and styrene-methylacrylate copolymer pyrolysis products,
Chromatographia, 1980, 13, 3, 151-156, https://doi.org/10.1007/BF02259304
. [all data]
Sivadier, Ratel, et al., 2009
Sivadier, G.; Ratel, J.; Engel, E.,
Latency and persistence of diet volatile biomarkers in lamb fats,
J. Agric. Food Chem., 2009, 57, 2, 645-652, https://doi.org/10.1021/jf802467q
. [all data]
Vasta, Ratel, et al., 2007
Vasta, V.; Ratel, J.; Engel, E.,
Mass Spectrometry Analysis of Volatile Compounds in Raw Meat for the Authentication of the Feeding Background of Farm Animals,
J. Agric. Food Chem., 2007, 55, 12, 4630-4639, https://doi.org/10.1021/jf063432n
. [all data]
Leffingwell and Alford, 2005
Leffingwell, J.C.; Alford, E.D.,
Volatile constituents of Perique tobacco,
Electron. J. Environ. Agric. Food Chem., 2005, 4, 2, 899-915. [all data]
Soria, Martinez-Castro, et al., 2008
Soria, A.C.; Martinez-Castro, I.; Sanz, J.,
Some aspects of dynamic headspace analysis of volatile components in honey,
Foog Res. International, 2008, 41, 8, 838-848, https://doi.org/10.1016/j.foodres.2008.07.010
. [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, IR Spectrum, Gas Chromatography, References
- Symbols used in this document:
AE Appearance energy Cp,liquid Constant pressure heat capacity of liquid EA Electron affinity Tboil Boiling point Tfus Fusion (melting) 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
- The National Institute of Standards and Technology (NIST) uses its best efforts to deliver a high quality copy of the Database and to verify that the data contained therein have been selected on the basis of sound scientific judgment. However, NIST makes no warranties to that effect, and NIST shall not be liable for any damage that may result from errors or omissions in the Database.
- Customer support for NIST Standard Reference Data products.