Cyclopropanecarbonitrile

Formula: C₄H₅N
Molecular weight: 67.0892
IUPAC Standard InChI: InChI=1S/C4H5N/c5-3-4-1-2-4/h4H,1-2H2
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
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Other names: Cyanocyclopropane; Cyclopropanenitrile; Cyclopropyl cyanide; Cyclopropylnitrile; Cyclopropanecarboxylic acid nitrile
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Gas phase thermochemistry data

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Data compiled by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Quantity	Value	Units	Method	Reference	Comment
Δ_fH°_gas	43.7 ± 0.2	kcal/mol	Ccb	Fuchs, Hallman, et al., 1982	Heat of combustion is not reported, see Hall and Baldt, 1971
Δ_fH°_gas	43.17	kcal/mol	Ccr	Hall and Baldt, 1971

Condensed phase thermochemistry data

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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
Δ_fH°_liquid	33.65	kcal/mol	Ccr	Hall and Baldt, 1971	ALS
Quantity	Value	Units	Method	Reference	Comment
Δ_cH°_liquid	-580.65 ± 0.17	kcal/mol	Ccr	Hall and Baldt, 1971	ALS
Δ_cH°_liquid	-581.5	kcal/mol	Ccb	Bruylants and Christiaen, 1925	ALS

Constant pressure heat capacity of liquid

C_p,liquid (cal/mol*K)	Temperature (K)	Reference	Comment
27.58	297.	Hall and Baldt, 1971	DH

Reaction thermochemistry data

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Data compiled by: John E. Bartmess

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Individual Reactions

C₄H₄N^- + = Cyclopropanecarbonitrile

By formula: C₄H₄N^- + H⁺ = C₄H₅N

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	375.4 ± 2.2	kcal/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
Δ_rG°	367.8 ± 2.0	kcal/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 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)	193.2	kcal/mol	N/A	Hunter and Lias, 1998	HL
Quantity	Value	Units	Method	Reference	Comment
Gas basicity	185.8	kcal/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^- + = Cyclopropanecarbonitrile

By formula: C₄H₄N^- + H⁺ = C₄H₅N

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	375.4 ± 2.2	kcal/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
Δ_rG°	367.8 ± 2.0	kcal/mol	IMRE	Bartmess, Scott, et al., 1979	gas phase; Acid: cyanocyclopropane; value altered from reference due to change in acidity scale; B

References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, Notes

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]

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

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Symbols used in this document:

AE	Appearance energy
C_p,liquid	Constant pressure heat capacity of liquid
Δ_cH°_liquid	Enthalpy of combustion of liquid at standard conditions
Δ_fH°_gas	Enthalpy of formation of gas at standard conditions
Δ_fH°_liquid	Enthalpy of formation of liquid at standard conditions
Δ_rG°	Free energy of reaction at standard conditions
Δ_rH°	Enthalpy of reaction at standard conditions

Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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