Benzonitrile, 4-formyl-

Formula: C₈H₅NO
Molecular weight: 131.1314
IUPAC Standard InChI: InChI=1S/C8H5NO/c9-5-7-1-3-8(6-10)4-2-7/h1-4,6H
IUPAC Standard InChIKey: WZWIQYMTQZCSKI-UHFFFAOYSA-N
CAS Registry Number: 105-07-7
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: Terephthalaldehydonitrile; p-Cyanobenzaldehyde; p-Formylbenzonitrile; Benzaldehyde, p-cyano-; Benzonitrile, p-formyl-; 4-Cyanobenzaldehyde; 4-Formylbenzonitrile; USAF KF-1; p-Cyanobenzenecarboxaldehyde; NSC 5091
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Other data available:
- Phase change data
- Mass spectrum (electron ionization)
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Gas phase ion energetics data

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
B - John E. Bartmess

Quantity	Value	Units	Method	Reference	Comment
Proton affinity (review)	190.5	kcal/mol	N/A	Hunter and Lias, 1998	HL
Quantity	Value	Units	Method	Reference	Comment
Gas basicity	183.2	kcal/mol	N/A	Hunter and Lias, 1998	HL

Electron affinity determinations

EA (eV)	Method	Reference	Comment
1.219 ± 0.087	IMRE	Chowdhury and Kebarle, 1986	ΔGea(423 K) = -28.1 kcal/mol; ΔSea (estimated) = 0. eu.; B
1.166 ± 0.087	IMRE	Mishima, Huh, et al., 1993	ΔGea(343 K)=-27.8 kcal/mol. Reanchored to EA(PhNO2), Kebarle and Chowdhury, 1987.; B

Ionization energy determinations

IE (eV)	Method	Reference	Comment
10.10	PE	Gal, Geribaldi, et al., 1985	Vertical value; LBLHLM

References

Go To: Top, Gas phase ion energetics data, Notes

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]

Chowdhury and Kebarle, 1986
Chowdhury, S.; Kebarle, P., Electron affinities of di- and tetracyanoethylene and cyanobenzenes based on measurements of gas-phase electron transfer equilibria, J. Am. Chem. Soc., 1986, 108, 5453. [all data]

Mishima, Huh, et al., 1993
Mishima, M.; Huh, C.; Nakamura, H.; Fujio, M.; Tsuno, Y., Electron Affinities of Benzaldehydes. Substituent Effects on Stabilities of Aromatic Radical Anions., Tetrahed. Lett., 1993, 34, 26, 4223, https://doi.org/10.1016/S0040-4039(00)60533-6 . [all data]

Kebarle and Chowdhury, 1987
Kebarle, P.; Chowdhury, S., Electron affinities and electron transfer reactions, Chem. Rev., 1987, 87, 513. [all data]

Gal, Geribaldi, et al., 1985
Gal, J.-F.; Geribaldi, S.; Pfister-Guillouzo, G.; Morris, D.G., Basicity of the carbonyl group. Part 12. Correlations between ionization potentials and lewis basicities in aromatic carbonyl compounds, J. Chem. Soc. Perkin Trans. 2, 1985, 103. [all data]

Notes

Go To: Top, Gas phase ion energetics data, References

Symbols used in this document:

EA Electron affinity
Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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