Benzamide

Formula: C₇H₇NO
Molecular weight: 121.1366
IUPAC Standard InChI: InChI=1S/C7H7NO/c8-7(9)6-4-2-1-3-5-6/h1-5H,(H2,8,9)
IUPAC Standard InChIKey: KXDAEFPNCMNJSK-UHFFFAOYSA-N
CAS Registry Number: 55-21-0
Chemical structure:
This structure is also available as a 2d Mol file or as a computed 3d SD file
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Species with the same structure:
- Benzamide
Other names: Benzoic acid amide; Benzoylamide; Phenylcarboxyamide
Information on this page:
Other data available:
Data at other public NIST sites:
- Gas Phase Kinetics Database
- X-ray Photoelectron Spectroscopy Database, version 5.0
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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)	892.1	kJ/mol	N/A	Hunter and Lias, 1998	HL
Quantity	Value	Units	Method	Reference	Comment
Gas basicity	861.2	kJ/mol	N/A	Hunter and Lias, 1998	HL

Ionization energy determinations

IE (eV)	Method	Reference	Comment
9.25	EI	Elder, Beynon, et al., 1976	LLK
9.60	EI	Benoit, 1973	LLK
9.4 ± 0.2	EI	Cotter, Soc. 1965	RDSH
9.45	PE	McAlduff, Lynch, et al., 1978	Vertical value; LLK

Appearance energy determinations

Ion	AE (eV)	Other Products	Method	Reference	Comment
C₆H₅⁺	14.21	NH₂+CO	EI	Benoit, 1973	LLK
C₆H₅⁺	13.5 ± 0.1	?	EI	Cotter, Soc. 1965	RDSH
C₇H₅N⁺	10.19 ± 0.10	H₂O	EI	Cotter, 1964	RDSH
C₇H₅O⁺	10.1	NH₂	EI	Elder, Beynon, et al., 1976	LLK
C₇H₅O⁺	11.09	NH₂	EI	Benoit, 1973	LLK
C₇H₅O⁺	9.9 ± 0.1	NH₂	EI	Cotter, Soc. 1965	RDSH

De-protonation reactions

C₇H₆NO^- + = Benzamide

By formula: C₇H₆NO^- + H⁺ = C₇H₇NO

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	1481. ± 8.8	kJ/mol	G+TS	Taft, 1987	gas phase; value altered from reference due to change in acidity scale; B
Quantity	Value	Units	Method	Reference	Comment
Δ_rG°	1452. ± 8.4	kJ/mol	IMRE	Taft, 1987	gas phase; value altered from reference due to change in acidity scale; B

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]

Elder, Beynon, et al., 1976
Elder, J.F.; Beynon, J.H.; Cooks, R.G., The benzoyl ion. Thermochemistry and kinetic energy release, Org. Mass Spectrom., 1976, 11, 415. [all data]

Benoit, 1973
Benoit, F., The benzoyl cation: The participation of isolated electronic excited states in the dissociation of molecular ions of the form [C₆H₅COX]⁺, Org. Mass Spectrom., 1973, 7, 1407. [all data]

Cotter, Soc. 1965
Cotter, J.L., Electron-impact fragmentation of pentafluorobenzamide, J. Chem., Soc. 1965, 5742. [all data]

McAlduff, Lynch, et al., 1978
McAlduff, E.J.; Lynch, B.M.; Houk, K.N., Photoelectron spectra of substituted benzamides, Can. J. Chem., 1978, 56, 495. [all data]

Cotter, 1964
Cotter, J.L., Electron impact fragmentation patterns of acetanilide and benzamide, J. Chem. Soc., 1964, 5477. [all data]

Taft, 1987
Taft, R.W., The Nature and Analysis of Substitutent Electronic Effects, Personal communication. See also Prog. Phys. Org. Chem., 1987, 16, 1. [all data]

Notes

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

Symbols used in this document:

AE Appearance energy

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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AE	Appearance energy
Δ_rG°	Free energy of reaction at standard conditions
Δ_rH°	Enthalpy of reaction at standard conditions