Benzamide, N,N-dimethyl-

• Formula: C₉H₁₁NO
• Molecular weight: 149.1897
• IUPAC Standard InChI: InChI=1S/C9H11NO/c1-10(2)9(11)8-6-4-3-5-7-8/h3-7H,1-2H3 Copy

  
• IUPAC Standard InChIKey: IMNDHOCGZLYMRO-UHFFFAOYSA-N Copy
• CAS Registry Number: 611-74-5
• 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: Dimethylbenzamide; N,N-Dimethylbenzamide
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• Information on this page:
  • Gas phase thermochemistry data
  • Condensed phase thermochemistry data
  • Phase change data
  • Reaction thermochemistry data
  • Gas phase ion energetics data
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • Gas Chromatography
  • References
  • Notes
• Other data available:
  • UV/Visible spectrum
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Gas phase 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: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Condensed phase 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: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

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:
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
BS - Robert L. Brown and Stephen E. Stein
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
AC - William E. Acree, Jr., James S. Chickos

Reduced pressure boiling point

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: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

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

=

By formula: C₉H₁₁NO = C₉H₁₁NO

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:
LBLHLM - Sharon G. Lias, John E. Bartmess, Joel F. Liebman, John L. Holmes, Rhoda D. Levin, and W. Gary Mallard

Ionization energy determinations

IR Spectrum

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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: NIST Mass Spectrometry Data Center, William E. Wallace, director

Gas Phase Spectrum

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Additional Data

Mass spectrum (electron ionization)

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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: NIST Mass Spectrometry Data Center, William E. Wallace, director

Spectrum

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Additional Data

Gas Chromatography

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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: NIST Mass Spectrometry Data Center, William E. Wallace, director

Kovats' RI, non-polar column, isothermal

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Kovats' RI, polar column, isothermal

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References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), Gas Chromatography, Notes

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

Abboud, Jimenez, et al., 1995
Abboud, J.-L.M.; Jimenez, P.; Roux, M.V.; Turrion, C.; Lopez-Mardomingo, C.; Podosenin, A.; Rogers, D.W.; Liebman, J.F., Interrelations of the energetics of amides and alkenes: enthalpies of formation of N,N-dimethyl dertivatives of pivalamide, 1-adamantylcarboxamide and benzamide, and of styrene and its a-, trans-β- and β,β-methylated derivates, J. Phys. Org. Chem., 1995, 8, 15-25. [all data]

Guthrie, Pike, et al., 1992
Guthrie, J.P.; Pike, D.C.; Lee, Y.-C., Equilibrium constants and heats of formation of methyl esters and N,N-dimethyl amides of substituted benzoic acids, Can. J. Chem., 1992, 70, 1671-1683. [all data]

Ryskalieva, Abramova, et al., 1991
Ryskalieva, A.K.; Abramova, G.V.; Nurakhmetov, N.N.; Erkasov, R.Sh., Thermochemistry of N,N'-acetylmethyl-carbamide and N,N-dimethylbenzamide, Russ. J. Phys. Chem. (Engl. Transl.), 1991, 65, 559-560. [all data]

Lieberman, 1955
Lieberman, S.V., The Use of the Disproportionation of Esters of 2-Propanenitronic Acid to Convert Halides to Carbonyl Compounds and Benzaldehyde to Benzamides, J. Am. Chem. Soc., 1955, 77, 1114. [all data]

Kuceski, 1968
Kuceski, V.P., , 1968. [all data]

Kuceski, 1966
Kuceski, V.P., , 1966. [all data]

Beak, Lee, et al., 1978
Beak, P.; Lee, J.-K.; Zeigler, J.M., Equilibration studies: amide-imidate and thioamide-thioimidate functions, J. Org. Chem., 1978, 43, 1536-1538. [all data]

Ribeiro Da Silva, Souza, et al., 1989
Ribeiro Da Silva, M.D.M.C.; Souza, P.; Pilcher, G., Enthalpies of combustion of thiobenzamide, N,N-dimethylthiobenzamide, and N,N-diethylthiobenzamide, J. Chem. Thermodyn., 1989, 21, 173-178. [all data]

Aldrich Chemical Company Inc., 1990
Aldrich Chemical Company Inc., Catalog Handbook of Fine Chemicals, Aldrich Chemical Company, Inc., Milwaukee WI, 1990, 1. [all data]

Frinton Laboratories Inc., 1986
Frinton Laboratories Inc., Catalog Number 11, Frinton Laboratories Inc., Vineland, NJ, 1986, 99. [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]

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]

Antonovic, Mijin, et al., 2000
Antonovic, D.G.; Mijin, D.Z.; Petrovic, S.D.; Stojanovic, N.D.; Nikolic, A.D., Gas chromatographic retention indices for the N-methyl-N-substituted benzamides on capillary columns, Indian J. Chem., 2000, 39B, 694-699. [all data]

Notes

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• Symbols used in this document:
  

  Tboil	Boiling point
  Tfus	Fusion (melting) point
  ΔcH°solid	Enthalpy of combustion of solid at standard conditions
  ΔfH°gas	Enthalpy of formation of gas at standard conditions
  ΔfH°solid	Enthalpy of formation of solid at standard conditions
  ΔrH°	Enthalpy of reaction at standard conditions
  ΔsubH°	Enthalpy of sublimation at standard conditions
  ΔvapH°	Enthalpy of vaporization at standard conditions

• Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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