Benzamide

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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
Tboil561.KN/ABuckingham and Donaghy, 1982BS
Quantity Value Units Method Reference Comment
Tfus401. ± 3.KAVGN/AAverage of 6 values; Individual data points
Quantity Value Units Method Reference Comment
Δsub24.3 ± 0.2kcal/molCGomez and Sabbah, 1982Based on data from 323. to 349. K.; AC

Enthalpy of sublimation

ΔsubH (kcal/mol) Temperature (K) Method Reference Comment
23.2333.5AStephenson and Malanowski, 1987Based on data from 325. to 342. K. See also Aihara, 1960.; AC

Enthalpy of fusion

ΔfusH (kcal/mol) Temperature (K) Method Reference Comment
5.6788403.N/ASteele, Chirico, et al., 1990DH
4.577402.1DSCBrittain, 2009AC
4.419402.3N/AAcree, 1991AC

In addition to the Thermodynamics Research Center (TRC) data available from this site, much more physical and chemical property data is available from the following TRC products:


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)213.2kcal/molN/AHunter and Lias, 1998HL
Quantity Value Units Method Reference Comment
Gas basicity205.8kcal/molN/AHunter and Lias, 1998HL

Ionization energy determinations

IE (eV) Method Reference Comment
9.25EIElder, Beynon, et al., 1976LLK
9.60EIBenoit, 1973LLK
9.4 ± 0.2EICotter, Soc. 1965RDSH
9.45PEMcAlduff, Lynch, et al., 1978Vertical value; LLK

Appearance energy determinations

Ion AE (eV) Other Products MethodReferenceComment
C6H5+14.21NH2+COEIBenoit, 1973LLK
C6H5+13.5 ± 0.1?EICotter, Soc. 1965RDSH
C7H5N+10.19 ± 0.10H2OEICotter, 1964RDSH
C7H5O+10.1NH2EIElder, Beynon, et al., 1976LLK
C7H5O+11.09NH2EIBenoit, 1973LLK
C7H5O+9.9 ± 0.1NH2EICotter, Soc. 1965RDSH

De-protonation reactions

C7H6NO- + Hydrogen cation = Benzamide

By formula: C7H6NO- + H+ = C7H7NO

Quantity Value Units Method Reference Comment
Δr354.0 ± 2.1kcal/molG+TSTaft, 1987gas phase; value altered from reference due to change in acidity scale; B
Quantity Value Units Method Reference Comment
Δr347.0 ± 2.0kcal/molIMRETaft, 1987gas phase; value altered from reference due to change in acidity scale; B

References

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

Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

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]

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]

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]

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

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