Cyclopropanecarbonitrile
- Formula: C4H5N
- Molecular weight: 67.0892
- IUPAC Standard InChIKey: AUQDITHEDVOTCU-UHFFFAOYSA-N
- CAS Registry Number: 5500-21-0
- 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: Cyanocyclopropane; Cyclopropanenitrile; Cyclopropyl cyanide; Cyclopropylnitrile; Cyclopropanecarboxylic acid nitrile
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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 | 182.7 ± 0.7 | kJ/mol | Ccb | Fuchs, Hallman, et al., 1982 | Heat of combustion is not reported, see Hall and Baldt, 1971 |
ΔfH°gas | 180.6 | kJ/mol | Ccr | Hall and Baldt, 1971 |
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 | 140.8 | kJ/mol | Ccr | Hall and Baldt, 1971 | ALS |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°liquid | -2429.4 ± 0.71 | kJ/mol | Ccr | Hall and Baldt, 1971 | ALS |
ΔcH°liquid | -2433. | kJ/mol | Ccb | Bruylants and Christiaen, 1925 | ALS |
Constant pressure heat capacity of liquid
Cp,liquid (J/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
115.4 | 297. | Hall and Baldt, 1971 | 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
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
AC - William E. Acree, Jr., James S. Chickos
DRB - Donald R. Burgess, Jr.
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tboil | 408.2 | K | N/A | Weast and Grasselli, 1989 | BS |
Tboil | 407. to 408. | K | N/A | Frinton Laboratories Inc., 1986 | BS |
Tboil | 408.2 | K | N/A | Majer and Svoboda, 1985 | |
Tboil | 404.9 | K | N/A | Hammond and Todd, 1954 | Uncertainty assigned by TRC = 3. K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 41. ± 2. | kJ/mol | AVG | N/A | Average of 6 values; Individual data points |
Enthalpy of vaporization
ΔvapH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
35.55 | 408.2 | N/A | Majer and Svoboda, 1985 | |
39.4 | 325. | BG | Baldt and Hall, 1971 | Based on data from 310. to 391. K.; AC |
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° | 1571. ± 9.2 | kJ/mol | G+TS | Bartmess, Scott, et al., 1979 | gas phase; Acid: cyanocyclopropane; 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; Acid: cyanocyclopropane; value altered from reference due to change in acidity scale |
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:
B - John E. Bartmess
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) | 808.2 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
Quantity | Value | Units | Method | Reference | Comment |
Gas basicity | 777.5 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
10.25 | PE | Willett and Baer, 1980 | LLK |
11.2 ± 0.2 | EI | Kiser and Hobrock, 1962 | RDSH |
Appearance energy determinations
Ion | AE (eV) | Other Products | Method | Reference | Comment |
---|---|---|---|---|---|
CH2N+ | 11.50 | ? | PI | Willett and Baer, 1980 | LLK |
CN+ | 19.5 ± 0.4 | ? | EI | Kiser and Hobrock, 1962 | RDSH |
C2H3+ | 12.65 | ? | PI | Willett and Baer, 1980 | LLK |
C2H3N+ | 11.00 | C2H2 | EI | Sakurai and Jennings, 1981 | LLK |
C2H3N+ | 11.00 | ? | PI | Willett and Baer, 1980 | LLK |
C3H2N+ | 11.75 | ? | PI | Willett and Baer, 1980 | LLK |
C3H3+ | 11.80 | ? | PI | Willett and Baer, 1980 | LLK |
C3H4+ | 11.20 | ? | PI | Willett and Baer, 1980 | LLK |
C3H5+ | 12.70 ± 0.15 | CN | EI | Kiser and Hobrock, 1962 | RDSH |
C4H4N+ | 12.10 | H | PI | Willett and Baer, 1980 | LLK |
De-protonation reactions
C4H4N- + =
By formula: C4H4N- + H+ = C4H5N
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 1571. ± 9.2 | kJ/mol | G+TS | Bartmess, Scott, et al., 1979 | gas phase; Acid: cyanocyclopropane; 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; Acid: cyanocyclopropane; value altered from reference due to change in acidity scale; B |
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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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 | RADIAN CORP |
NIST MS number | 69507 |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, 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.
Fuchs, Hallman, et al., 1982
Fuchs, R.; Hallman, J.H.; Perlman, M.O.,
Thermochemistry of conjugation of simple cyclopropane derivatives,
Can. J. Chem., 1982, 60, 1832-1835. [all data]
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]
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]
Frinton Laboratories Inc., 1986
Frinton Laboratories Inc.,
Catalog Number 11, Frinton Laboratories Inc., Vineland, NJ, 1986, 99. [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]
Hammond and Todd, 1954
Hammond, G.S.; Todd, R.W.,
The Low Reactivity of Cyclopropane Derivatives twoard Free Radicals,
J. Am. Chem. Soc., 1954, 76, 4081. [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]
Willett and Baer, 1980
Willett, G.D.; Baer, T.,
Thermochemistry and dissociation dynamics of state-selected C4H4X ions. 3. C4H5N+,
J. Am. Chem. Soc., 1980, 102, 6774. [all data]
Kiser and Hobrock, 1962
Kiser, R.W.; Hobrock, B.G.,
The ionization potentials of cyclopropyl radical and cyclopropyl cyanide,
J. Phys. Chem., 1962, 66, 957. [all data]
Sakurai and Jennings, 1981
Sakurai, H.; Jennings, K.R.,
A study of the structures of decomposing and non-decomposing [C4H5N]+ ions formed from different neutral species,
Org. Mass Spectrom., 1981, 16, 393. [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, Mass spectrum (electron ionization), References
- Symbols used in this document:
AE Appearance energy Cp,liquid Constant pressure heat capacity of liquid 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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