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Acetamide, N-methyl-

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Gas phase thermochemistry data

Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry 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 by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Quantity Value Units Method Reference Comment
Deltafgas-59.3 ± 1.3kcal/molCcbRoux, Jimenez, et al., 1996 

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

Quantity Value Units Method Reference Comment
Deltafliquid-74.87 ± 0.31kcal/molCcbVasil'eva and Zhil'tsova, 1982hf298 calculated possible error by authors
Quantity Value Units Method Reference Comment
Deltacliquid-446.39 ± 0.31kcal/molCcbVasil'eva and Zhil'tsova, 1982hf298 calculated possible error by authors
Quantity Value Units Method Reference Comment
Deltafsolid-76.2 ± 1.2kcal/molCcbRoux, Jimenez, et al., 1996 
Quantity Value Units Method Reference Comment
Deltacsolid-445.1 ± 1.2kcal/molCcbRoux, Jimenez, et al., 1996 

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, Kenneth Kroenlein director
AC - William E. Acree, Jr., James S. Chickos
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Quantity Value Units Method Reference Comment
Tboil478.2KN/AWeast and Grasselli, 1989BS
Quantity Value Units Method Reference Comment
Tfus303.43KN/ACasteel and Amis, 1974Uncertainty assigned by TRC = 0.2 K; TRC
Tfus302.90KN/ABoje and Hvidt, 1971Uncertainty assigned by TRC = 1. K; TRC
Tfus303.67KN/ABonner and Kim, 1970Uncertainty assigned by TRC = 0.15 K; TRC
Quantity Value Units Method Reference Comment
Deltasub16.9 ± 0.48kcal/molVRoux, Jimenez, et al., 1996ALS
Deltasub16.9 ± 0.48kcal/molN/ARoux, Jimenez, et al., 1996AC
Deltasub16.70 ± 0.074kcal/molN/AStarzewski, Wadso, et al., 1984AC

Enthalpy of vaporization

DeltavapH (kcal/mol) Temperature (K) Method Reference Comment
13.3378.N/ASchmelzer and Pusch, 1995Based on data from 363. - 414. K.; AC
15.368.N/AAucejo, Monton, et al., 1993Based on data from 353. - 428. K.; AC
14.2348.AStephenson and Malanowski, 1987Based on data from 333. - 443. K.; AC
12.8368.AStephenson and Malanowski, 1987Based on data from 353. - 479. K.; AC

Antoine Equation Parameters

log10(P) = A − (B / (T + C))
    P = vapor pressure (atm)
    T = temperature (K)

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Temperature (K) A B C Reference Comment
313. - 363.-0.07493144.114-277.873Gopal and Rizvi, 1968Coefficents calculated by NIST from author's data.

Enthalpy of sublimation

DeltasubH (kcal/mol) Temperature (K) Reference Comment
12.9288. - 303.Aihara, 1952See also Jones, 1960.; AC

Enthalpy of fusion

DeltafusH (kcal/mol) Temperature (K) Reference Comment
2.416303.7Ahlers, Lohmann, et al., 1999AC
2.33303.8Kreis and Wood, 1969AC

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:


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 as indicated in comments:
B - John E. Bartmess
M - Michael M. Meot-Ner (Mautner) and Sharon G. Lias
RCD - Robert C. Dunbar

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

MeCO2 anion + Acetamide, N-methyl- = (MeCO2 anion bullet Acetamide, N-methyl-)

By formula: C2H3O2- + C3H7NO = (C2H3O2- bullet C3H7NO)

Bond type: Hydrogen bonds of deprotonated acids to amides

Quantity Value Units Method Reference Comment
Deltar25.4 ± 1.0kcal/molTDAsMeot-ner, 1988gas phase; B,M
Quantity Value Units Method Reference Comment
Deltar27.4cal/mol*KPHPMSMeot-Ner (Mautner), 1988gas phase; M
Quantity Value Units Method Reference Comment
Deltar17.2 ± 1.0kcal/molTDAsMeot-ner, 1988gas phase; B

pyrrolide anion + Acetamide, N-methyl- = (pyrrolide anion bullet Acetamide, N-methyl-)

By formula: C4H4N- + C3H7NO = (C4H4N- bullet C3H7NO)

Quantity Value Units Method Reference Comment
Deltar27.kcal/molPHPMSMeot-Ner (Mautner), 1988gas phase; M
Quantity Value Units Method Reference Comment
Deltar30.cal/mol*KPHPMSMeot-Ner (Mautner), 1988gas phase; M

Free energy of reaction

DeltarG° (kcal/mol) T (K) Method Reference Comment
11.9497.PHPMSMeot-Ner (Mautner), 1988gas phase; M

C3H6NO- + Acetamide, N-methyl- = (C3H6NO- bullet Acetamide, N-methyl-)

By formula: C3H6NO- + C3H7NO = (C3H6NO- bullet C3H7NO)

Quantity Value Units Method Reference Comment
Deltar27.kcal/molPHPMSMeot-Ner (Mautner), 1988gas phase; M
Quantity Value Units Method Reference Comment
Deltar30.cal/mol*KPHPMSMeot-Ner (Mautner), 1988gas phase; M

Free energy of reaction

DeltarG° (kcal/mol) T (K) Method Reference Comment
12.5497.PHPMSMeot-Ner (Mautner), 1988gas phase; M

(MeCO2 anion bullet Acetamide, N-methyl-) + Acetamide, N-methyl- = (MeCO2 anion bullet 2Acetamide, N-methyl-)

By formula: (C2H3O2- bullet C3H7NO) + C3H7NO = (C2H3O2- bullet 2C3H7NO)

Bond type: Hydrogen bonds of deprotonated acids to amides

Quantity Value Units Method Reference Comment
Deltar17.6kcal/molPHPMSMeot-Ner (Mautner), 1988gas phase; M
Quantity Value Units Method Reference Comment
Deltar21.8cal/mol*KPHPMSMeot-Ner (Mautner), 1988gas phase; M

C3H8NO+ + Acetamide, N-methyl- = (C3H8NO+ bullet Acetamide, N-methyl-)

By formula: C3H8NO+ + C3H7NO = (C3H8NO+ bullet C3H7NO)

Bond type: Hydrogen bonds of the type OH-O between organics

Quantity Value Units Method Reference Comment
Deltar29.8kcal/molPHPMSMeot-Ner, 1984gas phase; M
Quantity Value Units Method Reference Comment
Deltar23.6cal/mol*KPHPMSMeot-Ner, 1984gas phase; M

C3H6NO- + Hydrogen cation = Acetamide, N-methyl-

By formula: C3H6NO- + H+ = C3H7NO

Quantity Value Units Method Reference Comment
Deltar361.8 ± 2.2kcal/molG+TSDecouzon, Exner, et al., 1990gas phase; B
Quantity Value Units Method Reference Comment
Deltar354.5 ± 2.0kcal/molIMREDecouzon, Exner, et al., 1990gas phase; B

Lithium ion (1+) + Acetamide, N-methyl- = (Lithium ion (1+) bullet Acetamide, N-methyl-)

By formula: Li+ + C3H7NO = (Li+ bullet C3H7NO)

Free energy of reaction

DeltarG° (kcal/mol) T (K) Method Reference Comment
41.4373.CIDT,ICRHerreros, Gal, et al., 1999RCD

Sodium ion (1+) + Acetamide, N-methyl- = (Sodium ion (1+) bullet Acetamide, N-methyl-)

By formula: Na+ + C3H7NO = (Na+ bullet C3H7NO)

Quantity Value Units Method Reference Comment
Deltar35.7kcal/molCIDTKlassen, Anderson, et al., 1996RCD

Potassium ion (1+) + Acetamide, N-methyl- = (Potassium ion (1+) bullet Acetamide, N-methyl-)

By formula: K+ + C3H7NO = (K+ bullet C3H7NO)

Quantity Value Units Method Reference Comment
Deltar30.4kcal/molCIDTKlassen, Anderson, et al., 1996RCD

IR Spectrum

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, 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 by: NIST Mass Spectrometry Data Center, William E. Wallace, director

Gas Phase Spectrum

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IR spectrum
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Additional Data

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Owner NIST Standard Reference Data Program
Collection (C) 2018 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
State gas
Instrument HP-GC/MS/IRD

This IR spectrum is from the NIST/EPA Gas-Phase Infrared Database .


Mass spectrum (electron ionization)

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry 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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Mass spectrum
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Additional Data

View image of digitized spectrum (can be printed in landscape orientation).

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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 Japan AIST/NIMC Database- Spectrum MS-NW-4322
NIST MS number 230310

All mass spectra in this site (plus many more) are available from the NIST/EPA/NIH Mass Spectral Library. Please see the following for information about the library and its accompanying search program.


References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry 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.

Roux, Jimenez, et al., 1996
Roux, M.V.; Jimenez, P.; Davalos, J.Z.; Castano, O.; Molina, M.T.; Notario, R.; Herreros, M.; Abboud, J.-L.M., The first direct experimental determination of strain in neutral and protonated 2-azetidinone, J. Am. Chem. Soc., 1996, 118, 12735-12737. [all data]

Vasil'eva and Zhil'tsova, 1982
Vasil'eva, T.F.; Zhil'tsova, E.N., Heat of combustion of two monomethylamides, Termodin. Organ. Soedin., 1982, 108-110. [all data]

Weast and Grasselli, 1989
CRC Handbook of Data on Organic Compounds, 2nd Editon, Weast,R.C and Grasselli, J.G., ed(s)., CRC Press, Inc., Boca Raton, FL, 1989, 1. [all data]

Casteel and Amis, 1974
Casteel, J.F.; Amis, E.S., Conductance of Sodium Perchlorate in Water-N-Methylacetamide (NMA) Solvent System, J. Chem. Eng. Data, 1974, 19, 121. [all data]

Boje and Hvidt, 1971
Boje, L.; Hvidt, A., Densities of aqueous mixtures of non-electrolytes, J. Chem. Thermodyn., 1971, 3, 663. [all data]

Bonner and Kim, 1970
Bonner, O.D.; Kim, S.J., Intermolecular Association in Structured Liquids 1. Ethylene Carbonate and N-Methylacetamide, J. Chem. Thermodyn., 1970, 2, 63. [all data]

Starzewski, Wadso, et al., 1984
Starzewski, P.; Wadso, I.; Zielenkiewicz, W., Enthalpies of vaporization of some N-alkylamides at 298.15 K, J. Chem. Thermodyn., 1984, 16, 331-334. [all data]

Schmelzer and Pusch, 1995
Schmelzer, Jürgen; Pusch, Jens, Phase equilibria in binary systems containing N-monosubstituted amides and hydrocarbons, Fluid Phase Equilibria, 1995, 110, 1-2, 183-196, https://doi.org/10.1016/0378-3812(95)02753-2 . [all data]

Aucejo, Monton, et al., 1993
Aucejo, Antonio; Monton, Juan B.; Munoz, Rosa; Sanchotello, Margarita, Isobaric vapor-liquid equilibrium data for the cyclohexanone + N-methylacetamide system, J. Chem. Eng. Data, 1993, 38, 1, 160-162, https://doi.org/10.1021/je00009a039 . [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]

Gopal and Rizvi, 1968
Gopal, R.; Rizvi, S.A., Vapour Pressures of Some Mono- and Di-Alkyl Substituted Aliphatic Amides at Different Temperatures, J. Indian Chem. Soc., 1968, 45, 1, 13-16. [all data]

Aihara, 1952
Aihara, A., J. Chem. Soc. Jpn. Pure Chem. Sect., 1952, 73, 855. [all data]

Jones, 1960
Jones, A.H., Sublimation Pressure Data for Organic Compounds., J. Chem. Eng. Data, 1960, 5, 2, 196-200, https://doi.org/10.1021/je60006a019 . [all data]

Ahlers, Lohmann, et al., 1999
Ahlers, Jens; Lohmann, Jürgen; Gmehling, Jürgen, Binary Solid-Liquid Equilibria of Organic Systems Containing Different Amides and Sulfolane, J. Chem. Eng. Data, 1999, 44, 4, 727-730, https://doi.org/10.1021/je9802975 . [all data]

Kreis and Wood, 1969
Kreis, R.W.; Wood, R.H., Enthalpy of fusion and cryoscopic constant of N-methylacetamide, The Journal of Chemical Thermodynamics, 1969, 1, 6, 523-526, https://doi.org/10.1016/0021-9614(69)90012-3 . [all data]

Meot-ner, 1988
Meot-ner, M., Ionic Hydrogen Bond and Ion Solvation. 6. Interaction Energies of the Acetate Ion with Organic Molecules. Comparison of CH3COO- with Cl-, CN-, and SH-, J. Am. Chem. Soc., 1988, 110, 12, 3854, https://doi.org/10.1021/ja00220a022 . [all data]

Meot-Ner (Mautner), 1988
Meot-Ner (Mautner), M., Models for Strong Interactions in Proteins and Enzymes. 2. Interactions of Ions with the Peptide Link and Imidazole, J. Am. Chem. Soc., 1988, 110, 10, 3075, https://doi.org/10.1021/ja00218a014 . [all data]

Meot-Ner, 1984
Meot-Ner, (Mautner), The Ionic Hydrogen Bond. 4. Intramolecular and Multiple Bonds. Proton Affinities, Hydration and Complexes of Amides and Amino Acid Derivatives, J. Am. Chem. Soc., 1984, 106, 2, 278, https://doi.org/10.1021/ja00314a003 . [all data]

Decouzon, Exner, et al., 1990
Decouzon, M.; Exner, O.; Gal, J.-F.; Maria, P.-C., The Gas-Phase Acidity and the Acidic Site of Acetohydroxamic Acid: an FT-ICR Study, J. Org. Chem., 1990, 55, 13, 3980, https://doi.org/10.1021/jo00300a007 . [all data]

Herreros, Gal, et al., 1999
Herreros, M.; Gal, J.-F.; Maria, P.-C.; Decouzon, M., Gas-Phase Basicity of Simple Amides Toward Proton and Lithium Cation: An Experimental and Theoretical Study, Eur. J. Mass Spectrom., 1999, 5, 1, 259, https://doi.org/10.1255/ejms.282 . [all data]

Klassen, Anderson, et al., 1996
Klassen, J.S.; Anderson, S.G.; Blades, A.T.; Kebarle, P., Reaction Enthalpies for M+L = M+ + L, Where M+ = Na+ and K+ and L = Acetamide, N-Methylacetamide, N,N-Dimethylacetamide, Glycine, and Glycylglycine, from Determinations of the Collision-Induced Dissociation Thresholds, J. Phys. Chem., 1996, 100, 33, 14218, https://doi.org/10.1021/jp9608382 . [all data]


Notes

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