Benzoic acid, 4-cyano-, methyl ester

Formula: C₉H₇NO₂
Molecular weight: 161.1574
IUPAC Standard InChI: InChI=1S/C9H7NO2/c1-12-9(11)8-4-2-7(6-10)3-5-8/h2-5H,1H3
IUPAC Standard InChIKey: KKZMIDYKRKGJHG-UHFFFAOYSA-N
CAS Registry Number: 1129-35-7
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: Benzoic acid, p-cyano-, methyl ester; p-Cyanobenzoic acid methyl ester; Methyl p-cyanobenzoate; Methyl 4-cyanobenzoate; 4-Cyanobenzoic acid methyl ester
Permanent link for this species. Use this link for bookmarking this species for future reference.
Information on this page:
Other data available:
- Phase change data
- Mass spectrum (electron ionization)
Options:
- Switch to calorie-based units

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:
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)	816.6	kJ/mol	N/A	Hunter and Lias, 1998	HL
Quantity	Value	Units	Method	Reference	Comment
Gas basicity	785.6	kJ/mol	N/A	Hunter and Lias, 1998	HL

Electron affinity determinations

EA (eV)	Method	Reference	Comment
0.980 ± 0.087	IMRE	Huh, Kang, et al., 1999	ΔG(EA) 343K; anchored to ΔG value. Including anchor ΔS, EA is ca. 0.4 kcal/mol more bound.; B
0.850 ± 0.087	IMRE	Mishima, Huh, et al., 1995	ΔGea(343 K)=-19.0 kcal/mol Reanchored to EA(PhNO2), Kebarle and Chowdhury, 1987.; B

Ionization energy determinations

IE (eV)	Method	Reference	Comment
9.72	EI	Howe and Williams, 1969	RDSH

Appearance energy determinations

Ion	AE (eV)	Other Products	Method	Reference	Comment
C₈H₄NO⁺	11.60	CH₃O	EI	Howe and Williams, 1969	RDSH

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]

Huh, Kang, et al., 1999
Huh, C.; Kang, C.H.; Lee, H.W.; Nakamura, H.; Mishima, M.; Tsuno, Y.; Yamataka, H., Thermodynamic stabilities and resonance demand of aromatic radical anions in the gas phase, Bull. Chem. Soc. Japan, 1999, 72, 5, 1083-1091, https://doi.org/10.1246/bcsj.72.1083 . [all data]

Mishima, Huh, et al., 1995
Mishima, M.; Huh, C.; Lee, H.W.; Nakamura, H.; Fujio, M.; Tsuno, Y., Electron affinities of acetophenones and methyl benzoates. Varying resonance demand of aromatic radical anions, Tetrahed. Lett., 1995, 36, 13, 2265, https://doi.org/10.1016/0040-4039(95)00267-G . [all data]

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

Howe and Williams, 1969
Howe, I.; Williams, D.H., Calculation and qualitative predictions of mass spectra. Mono- and paradisubstituted benzenes, J. Am. Chem. Soc., 1969, 91, 7137. [all data]

Notes

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

Symbols used in this document:

AE Appearance energy

EA Electron affinity
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.