Butanenitrile
- Formula: C4H7N
- Molecular weight: 69.1051
- IUPAC Standard InChIKey: KVNRLNFWIYMESJ-UHFFFAOYSA-N
- CAS Registry Number: 109-74-0
- 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: Butyronitrile; n-Butyronitrile; Butyrylonitrile; Propyl cyanide; 1-Cyanopropane; n-C3H7CN; n-Butanitrile; n-Butanenitrile; Butyric acid nitrile; Propylkyanid; UN 2411; NSC 8412
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Gas phase thermochemistry data
Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Henry's Law data, Gas phase ion energetics data, Ion clustering 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 |
---|---|---|---|---|---|
ΔfH°gas | 31.2 | kJ/mol | Ccb | Evans and Skinner, 1959 | |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°gas | -2568.7 ± 0.92 | kJ/mol | Ccb | Evans and Skinner, 1959 |
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 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 | -5.8 ± 1.0 | kJ/mol | Ccb | Evans and Skinner, 1959 | ALS |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°liquid | -2579. | kJ/mol | Ccb | Lemoult and Jungfleisch, 1909 | ALS |
Constant pressure heat capacity of liquid
Cp,liquid (J/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
134.2 | 298.15 | Mirzaliev, Shakhuradov, et al., 1987 | T = 173 to 373 K. Unsmoothed experimental datum given as 1.930 kJ/kg*K at 293 K. Cp (liq) = 1.8787 + 0.0018882T/K + 7.0408x10-6T2/K2 kJ/kg*K (173 to 373 K). Note, second coefficient should be negative.; DH |
134.9 | 303.15 | Guseinov and Mirzaliev, 1985 | T = 303 to 383 K. p = 0.1 MPa. Unsmoothed experimental datum given as 1.9520 kJ/kg*K.; DH |
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
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
AC - William E. Acree, Jr., James S. Chickos
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DRB - Donald R. Burgess, Jr.
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tboil | 391. ± 1. | K | AVG | N/A | Average of 23 out of 25 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 161.25 | K | N/A | Anonymous, 1957 | Uncertainty assigned by TRC = 0.6 K; TRC |
Tfus | 161.15 | K | N/A | Timmermans, 1935 | Uncertainty assigned by TRC = 0.5 K; TRC |
Tfus | 160. | K | N/A | Joukovsky, 1934 | Uncertainty assigned by TRC = 2. K; TRC |
Tfus | 161.25 | K | N/A | Timmermans and Delcourt, 1934 | Uncertainty assigned by TRC = 0.5 K; TRC |
Tfus | 160.9 | K | N/A | Timmermans, 1927 | Uncertainty assigned by TRC = 0.5 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Tc | 585.4 | K | N/A | Castillo-Lopez and Trejo Rodriguez, 1987 | Uncertainty assigned by TRC = 0.2 K; Visual, TE with digital voltmeter cal. by meas. on alkanes.; TRC |
Tc | 582.1 | K | N/A | Guye and Mallet, 1902 | Uncertainty assigned by TRC = 2. K; TRC |
Tc | 582.25 | K | N/A | Guye and Mallet, 1902, 2 | Uncertainty assigned by TRC = 0.9 K; TRC |
Tc | 582.15 | K | N/A | Guye and Mallet, 1902, 2 | Uncertainty assigned by TRC = 0.9 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Pc | 38.0 ± 0.7 | bar | AVG | N/A | Average of 6 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 38. ± 3. | kJ/mol | AVG | N/A | Average of 7 values; Individual data points |
Enthalpy of vaporization
ΔvapH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
33.68 | 390.8 | N/A | Majer and Svoboda, 1985 | |
37.7 | 347. | A,EB | Stephenson and Malanowski, 1987 | Based on data from 332. to 401. K. See also Stull, 1947 and Meyer and Hotz, 1973.; AC |
38.8 | 318. | EB | Meyer, Renner, et al., 1971 | Based on data from 303. to 493. 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 |
---|---|---|---|---|
332.96 to 400.86 | 3.2540 ± 0.0004 | 1452.08 ± 0.80 | -48.964 ± 0.028 | Meyer and Hotz, 1973 |
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: Michael M. Meot-Ner (Mautner) and Sharon G. Lias
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
By formula: CH6N+ + C4H7N = (CH6N+ • C4H7N)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 118. | kJ/mol | PHPMS | Speller and Meot-Ner (Mautner), 1985 | gas phase; Entropy change calculated or estimated |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 110. | J/mol*K | N/A | Speller and Meot-Ner (Mautner), 1985 | gas phase; Entropy change calculated or estimated |
By formula: H4N+ + C4H7N = (H4N+ • C4H7N)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 119. | kJ/mol | PHPMS | Speller and Meot-Ner (Mautner), 1985 | gas phase |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 90.4 | J/mol*K | PHPMS | Speller and Meot-Ner (Mautner), 1985 | gas phase |
Henry's Law 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: Rolf Sander
Henry's Law constant (water solution)
kH(T) = k°H exp(d(ln(kH))/d(1/T) ((1/T) - 1/(298.15 K)))
k°H = Henry's law constant for solubility in water at 298.15 K (mol/(kg*bar))
d(ln(kH))/d(1/T) = Temperature dependence constant (K)
k°H (mol/(kg*bar)) | d(ln(kH))/d(1/T) (K) | Method | Reference |
---|---|---|---|
19. | M | N/A |
Gas phase ion energetics 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 evaluated as indicated in comments:
HL - Edward P. Hunter and Sharon G. Lias
Data compiled as indicated in comments:
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
B - John E. Bartmess
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Proton affinity (review) | 798.4 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
Quantity | Value | Units | Method | Reference | Comment |
Gas basicity | 767.7 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
Electron affinity determinations
EA (eV) | Reference | Comment |
---|---|---|
0.016089 ± 0.000087 | Hammer, Diri, et al., 2003 | B |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
11.2 | PE | Ohno, Matumoto, et al., 1984 | LBLHLM |
11.8 ± 0.25 | EI | Chess, Lapp, et al., 1982 | LBLHLM |
11.67 ± 0.05 | PI | Watanabe, Nakayama, et al., 1962 | RDSH |
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 |
---|---|---|---|---|---|
C2H2+ | 15.50 | ? | EI | Heerma, deRidder, et al., 1969 | RDSH |
C2H3+ | 15.10 | ? | EI | Heerma, deRidder, et al., 1969 | RDSH |
C2H3N+ | 12.46 | ? | EI | Heerma, deRidder, et al., 1969 | RDSH |
C2H5+ | 12.97 | ? | EI | Heerma, deRidder, et al., 1969 | RDSH |
C4H6N+ | 13.00 | H | EI | Heerma, deRidder, et al., 1969 | RDSH |
Ion clustering data
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Henry's Law data, Gas phase ion energetics 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: Michael M. Meot-Ner (Mautner) and Sharon G. Lias
Note: Please consider using the reaction search for this species. This page allows searching of all reactions involving this species. Searches may be limited to ion clustering reactions. A general reaction search form is also available.
Clustering reactions
By formula: CH6N+ + C4H7N = (CH6N+ • C4H7N)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 118. | kJ/mol | PHPMS | Speller and Meot-Ner (Mautner), 1985 | gas phase; Entropy change calculated or estimated |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 110. | J/mol*K | N/A | Speller and Meot-Ner (Mautner), 1985 | gas phase; Entropy change calculated or estimated |
By formula: H4N+ + C4H7N = (H4N+ • C4H7N)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 119. | kJ/mol | PHPMS | Speller and Meot-Ner (Mautner), 1985 | gas phase |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 90.4 | J/mol*K | PHPMS | Speller and Meot-Ner (Mautner), 1985 | gas phase |
IR 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.
Data compiled by: Coblentz Society, Inc.
Spectrum
A digitized version of this spectrum is not currently available.
Additional Data
View scan of original (hardcopy) spectrum.
Owner | COBLENTZ SOCIETY Collection (C) 2018 copyright by the U.S. Secretary of Commerce on behalf of the United States of America. All rights reserved. |
---|---|
Source reference | COBLENTZ NO. 2557 |
Date | Not specified, most likely prior to 1970 |
Instrument | Not specified, most likely a prism, grating, or hybrid spectrometer. |
Data processing | (NO SPECTRUM, ONLY SCANNED IMAGE IS AVAILABLE) |
Mass spectrum (electron ionization)
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Henry's Law data, Gas phase ion energetics data, Ion clustering 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
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Additional Data
View image of digitized spectrum (can be printed in landscape orientation).
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 | Japan AIST/NIMC Database- Spectrum MS-NW- 927 |
NIST MS number | 228226 |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Henry's Law data, Gas phase ion energetics data, Ion clustering 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.
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]
Lemoult and Jungfleisch, 1909
Lemoult, M.P.; Jungfleisch, M.E.,
Thermochimie. - Comparaisons entre les nitriles et les carbylamines,
Compt. Rend., 1909, 148, 1602-1604. [all data]
Mirzaliev, Shakhuradov, et al., 1987
Mirzaliev, A.A.; Shakhuradov, Sh.G.; Guseinov, S.O.,
Investigation of the isobaric heat capacity of nitriles at different temperatures, Izv. Vyssh. Ucheb. Zaved.,
Neft i Gaz, 1987, 30(4), 55-58. [all data]
Guseinov and Mirzaliev, 1985
Guseinov, S.O.; Mirzaliev, A.A.,
Experimental investigation of volumetric and isobaric heat capacity of saturated nitriles at elevated temperatures and different pressures, Izv. Vyssh. Ucheb. Zaved.,
Neft i Gaz, 1985, 28(5), 58-62. [all data]
Anonymous, 1957
Anonymous, R.,
, Am. Pet. Inst. Res. Proj. 6, Carnegie-Mellon Univ., 1957. [all data]
Timmermans, 1935
Timmermans, J.,
Researches in Stoichiometry. I. The Heat of Fusion of Organic Compounds.,
Bull. Soc. Chim. Belg., 1935, 44, 17-40. [all data]
Joukovsky, 1934
Joukovsky, N.I.,
Experimental Study of the Theory of Concentrated Solutions. XI. Thermodynamic Properties of Concentrated Solutions of Aliphatic Organic Compounds Containing Nitrogen.,
Bull. Soc. Chim. Belg., 1934, 43, 397. [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]
Timmermans, 1927
Timmermans, J.,
The Melting Point of Organic Substances,
Bull. Soc. Chim. Belg., 1927, 36, 502. [all data]
Castillo-Lopez and Trejo Rodriguez, 1987
Castillo-Lopez, N.; Trejo Rodriguez, A.,
The critical temperatures and pressures of several n-alkanenitriles,
J. Chem. Thermodyn., 1987, 19, 671. [all data]
Guye and Mallet, 1902
Guye, P.A.; Mallet, E.,
Critical Constant and Molecular Complexity of Several Organic Compds.,
C. R. Hebd. Seances Acad. Sci., 1902, 133, 168. [all data]
Guye and Mallet, 1902, 2
Guye, P.A.; Mallet, E.,
Measurement of Critical Constants,
Arch. Sci. Phys. Nat., 1902, 13, 274-296. [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]
Meyer and Hotz, 1973
Meyer, Edwin F.; Hotz, Roger D.,
High-precision vapor-pressure data for eight organic compounds,
J. Chem. Eng. Data, 1973, 18, 4, 359-362, https://doi.org/10.1021/je60059a008
. [all data]
Meyer, Renner, et al., 1971
Meyer, Edwin F.; Renner, Terrence A.; Stec, Kenneth S.,
Cohesive energies in polar organic liquids. II. n-Alkane nitriles and the 1-chloro alkanes,
J. Phys. Chem., 1971, 75, 5, 642-648, https://doi.org/10.1021/j100675a008
. [all data]
Speller and Meot-Ner (Mautner), 1985
Speller, C.V.; Meot-Ner (Mautner), M.,
The Ionic Hydrogen Bond and Ion Solvation. 3. Bonds Involving Cyanides. Correlations with Proton Affinites,
J. Phys. Chem., 1985, 81, 24, 5217, https://doi.org/10.1021/j100270a020
. [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]
Chess, Lapp, et al., 1982
Chess, E.K.; Lapp, R.L.; Gross, M.L.,
The question of tautomerism of alkylnitrile and isonitrile radical cations,
Org. Mass Spectrom., 1982, 17, 475. [all data]
Watanabe, Nakayama, et al., 1962
Watanabe, K.; Nakayama, T.; Mottl, J.,
Ionization potentials of some molecules,
J. Quant. Spectry. Radiative Transfer, 1962, 2, 369. [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, deRidder, et al., 1969
Heerma, W.; deRidder, J.J.; Dijkstra, G.,
The electron-impact-induced fragmentation of n-alkyl cyanides,
Org. Mass Spectrom., 1969, 2, 1103. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Henry's Law data, Gas phase ion energetics data, Ion clustering data, IR Spectrum, Mass spectrum (electron ionization), References
- Symbols used in this document:
AE Appearance energy Cp,liquid Constant pressure heat capacity of liquid EA Electron affinity Pc Critical pressure Tboil Boiling point Tc Critical temperature Tfus Fusion (melting) point d(ln(kH))/d(1/T) Temperature dependence parameter for Henry's Law constant k°H Henry's Law constant at 298.15K ΔcH°gas Enthalpy of combustion of gas at standard conditions 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 ΔrH° Enthalpy of reaction at standard conditions ΔrS° Entropy 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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