Benzamide
- Formula: C7H7NO
- Molecular weight: 121.1366
- 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
The 3d structure may be viewed using Java or Javascript. - Species with the same structure:
- Other names: Benzoic acid amide; Benzoylamide; Phenylcarboxyamide
- Information on this page:
- Other data available:
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Condensed phase thermochemistry data
Go To: Top, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), References, Notes
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°solid | -202.14 ± 0.60 | kJ/mol | Ccr | Steele, Chirico, et al., 1990 | ALS |
ΔfH°solid | -204.8 ± 0.8 | kJ/mol | Ccb | Kulagina and Kiparisova, 1987 | ALS |
ΔfH°solid | -208.5 ± 1.9 | kJ/mol | Ccb | Nurachmetov, Beremzhanov, et al., 1985 | ALS |
ΔfH°solid | -202.8 | kJ/mol | Cm | Cole and Gilbert, 1951 | ALS |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°solid | -3552.8 ± 0.5 | kJ/mol | Ccr | Steele, Chirico, et al., 1990 | ALS |
ΔcH°solid | -3550.1 ± 0.8 | kJ/mol | Ccb | Kulagina and Kiparisova, 1987 | ALS |
ΔcH°solid | -3546.5 ± 1.9 | kJ/mol | Ccb | Nurachmetov, Beremzhanov, et al., 1985 | ALS |
ΔcH°solid | -3552.2 | kJ/mol | Cm | Cole and Gilbert, 1951 | ALS |
ΔcH°solid | -3551. ± 3. | kJ/mol | Ccb | Anderson and Gilbert, 1942 | ALS |
Constant pressure heat capacity of solid
Cp,solid (J/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
153.8 | 298.15 | Steele, Chirico, et al., 1990 | T = 315 to 475 K. C/R(c) = 0.067T - 1.51 (315 to 375 K); C/R(liq) = 0.0288T + 21.03 (415 to 475 K), R = 8.31441 JK mol.; 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
AC - William E. Acree, Jr., James S. Chickos
DH - Eugene S. Domalski and Elizabeth D. Hearing
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tboil | 561. | K | N/A | Buckingham and Donaghy, 1982 | BS |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 401. ± 3. | K | AVG | N/A | Average of 6 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
ΔsubH° | 102. ± 1. | kJ/mol | C | Gomez and Sabbah, 1982 | Based on data from 323. to 349. K.; AC |
Enthalpy of sublimation
ΔsubH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
96.9 | 333.5 | A | Stephenson and Malanowski, 1987 | Based on data from 325. to 342. K. See also Aihara, 1960.; AC |
Enthalpy of fusion
ΔfusH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
23.760 | 403. | N/A | Steele, Chirico, et al., 1990 | DH |
19.15 | 402.1 | DSC | Brittain, 2009 | AC |
18.49 | 402.3 | N/A | Acree, 1991 | 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
C7H6NO- + =
By formula: C7H6NO- + H+ = C7H7NO
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 1481. ± 8.8 | kJ/mol | G+TS | Taft, 1987 | gas phase; value altered from reference due to change in acidity scale |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 1452. ± 8.4 | kJ/mol | IMRE | Taft, 1987 | gas phase; 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) | 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- + =
By formula: C7H6NO- + H+ = C7H7NO
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 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 |
ΔrG° | 1452. ± 8.4 | kJ/mol | IMRE | Taft, 1987 | gas phase; value altered from reference due to change in acidity scale; B |
IR Spectrum
Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Mass spectrum (electron ionization), References, Notes
Data compiled by: Coblentz Society, Inc.
- SOLID (NUJOL MULL); BECKMAN IR-7 (GRATING); DIGITIZED BY NIST FROM HARD COPY (FROM TWO SEGMENTS); 4 cm-1 resolution
- SOLID (SPLIT MULL, FLUOROLUBE FOR 3800-1333 AND NUJOL FOR 1333-420 CM -1); BECKMAN IR-9 (GRATING); DIGITIZED BY NIST FROM HARD COPY (FROM TWO SEGMENTS); 4 cm-1 resolution
Data compiled by: Timothy J. Johnson, Tanya L. Myers, Yin-Fong Su, Russell G. Tonkyn, Molly Rose K. Kelly-Gorham, and Tyler O. Danby
Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director
Mass spectrum (electron ionization)
Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, References, Notes
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
View image of digitized spectrum (can be printed in landscape orientation).
Due to licensing restrictions, this spectrum cannot be downloaded.
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 | NIST Mass Spectrometry Data Center, 1994 |
NIST MS number | 135755 |
References
Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, 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.
Steele, Chirico, et al., 1990
Steele, W.V.; Chirico, R.D.; Nguyen, A.; Hossenlopp, I.A.; Smith, N.K.,
Determination of ideal-gas enthalpies of formation for key compounds,
Am. Inst. Chem. Eng. Symp. Ser. (AIChE Symp. Ser.), 1990, 138-154. [all data]
Kulagina and Kiparisova, 1987
Kulagina, T.G.; Kiparisova, E.G.,
Enthalpies of combustion and of formation of derivatives of carbamide,
Russ. J. Phys. Chem. (Engl. Transl.), 1987, 61, 261-262. [all data]
Nurachmetov, Beremzhanov, et al., 1985
Nurachmetov, N.N.; Beremzhanov, B.A.; Abramova, G.V.; Lebedev, B.V.,
Thermodynamics of (thio)amides and their compounds with mineral acids at (0-330)K,
Thermochim. Acta, 1985, 92, 329-332. [all data]
Cole and Gilbert, 1951
Cole, L.G.; Gilbert, E.C.,
The heats of combustion of some nitrogen compounds and the apparent energy of the N-N bond,
J. Am. Chem. Soc., 1951, 73, 5423-5427. [all data]
Anderson and Gilbert, 1942
Anderson, C.M.; Gilbert, E.C.,
The apparent energy of the N-N bond as calculated from heats of combustion,
J. Am. Chem. Soc., 1942, 64, 2369-2372. [all data]
Buckingham and Donaghy, 1982
Buckingham, J.; Donaghy, S.M.,
Dictionary of Organic Compounds: Fifth Edition, Chapman and Hall, New York, 1982, 1. [all data]
Gomez and Sabbah, 1982
Gomez, L.A.T.; Sabbah, R.,
Thermodynamique de substances azotees. IX. Etude thermochimique de la benzamide. Comparaison des grandeurs energetiques liees a la structure de quelques amides et thioamides,
Thermochim. Acta, 1982, 58, 311-315. [all data]
Stephenson and Malanowski, 1987
Stephenson, Richard M.; Malanowski, Stanislaw,
Handbook of the Thermodynamics of Organic Compounds, 1987, https://doi.org/10.1007/978-94-009-3173-2
. [all data]
Aihara, 1960
Aihara, Ariyuki,
Estimation of the Energy of Hydrogen Bonds Formed in Crystals. III. Amides,
Bull. Chem. Soc. Jpn., 1960, 33, 9, 1188-1194, https://doi.org/10.1246/bcsj.33.1188
. [all data]
Brittain, 2009
Brittain, Harry G.,
Vibrational Spectroscopic Studies of Cocrystals and Salts. 1. The Benzamide-Benzoic Acid System,
Crystal Growth & Design, 2009, 9, 5, 2492-2499, https://doi.org/10.1021/cg801397t
. [all data]
Acree, 1991
Acree, William E.,
Thermodynamic properties of organic compounds: enthalpy of fusion and melting point temperature compilation,
Thermochimica Acta, 1991, 189, 1, 37-56, https://doi.org/10.1016/0040-6031(91)87098-H
. [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]
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]
Notes
Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), References
- Symbols used in this document:
AE Appearance energy Cp,solid Constant pressure heat capacity of solid Tboil Boiling point Tfus Fusion (melting) point ΔcH°solid Enthalpy of combustion of solid at standard conditions ΔfH°solid Enthalpy of formation of solid at standard conditions ΔfusH Enthalpy of fusion ΔrG° Free energy of reaction at standard conditions ΔrH° Enthalpy of reaction at standard conditions ΔsubH Enthalpy of sublimation ΔsubH° Enthalpy of sublimation at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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