N,N-Dimethylacetamide

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Reaction thermochemistry data

Go To: Top, Gas phase ion energetics data, Ion clustering data, IR Spectrum, Mass spectrum (electron ionization), Gas Chromatography, 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:
M - Michael M. Meot-Ner (Mautner) and Sharon G. Lias
B - John E. Bartmess
RCD - Robert C. Dunbar
ALS - 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

C3H10N+ + N,N-Dimethylacetamide = (C3H10N+ • N,N-Dimethylacetamide)

By formula: C3H10N+ + C4H9NO = (C3H10N+ • C4H9NO)

Bond type: Hydrogen bonds of the type NH+-O between organics

Quantity Value Units Method Reference Comment
Δr114.kJ/molPHPMSMeot-Ner, 1984gas phase; M
Δr114.kJ/molPHPMSMeot-Ner, 1984, 2gas phase; M
Quantity Value Units Method Reference Comment
Δr101.J/mol*KPHPMSMeot-Ner, 1984gas phase; M
Δr101.J/mol*KPHPMSMeot-Ner, 1984, 2gas phase; M

C4H8NO- + Hydrogen cation = N,N-Dimethylacetamide

By formula: C4H8NO- + H+ = C4H9NO

Quantity Value Units Method Reference Comment
Δr1568. ± 8.8kJ/molG+TSBartmess, Scott, et al., 1979gas phase; value altered from reference due to change in acidity scale; B
Quantity Value Units Method Reference Comment
Δr1540. ± 8.4kJ/molIMREBartmess, Scott, et al., 1979gas phase; value altered from reference due to change in acidity scale; B

C4H10NO+ + N,N-Dimethylacetamide = (C4H10NO+ • N,N-Dimethylacetamide)

By formula: C4H10NO+ + C4H9NO = (C4H10NO+ • C4H9NO)

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

Quantity Value Units Method Reference Comment
Δr131.kJ/molPHPMSMeot-Ner, 1984, 2gas phase; M
Quantity Value Units Method Reference Comment
Δr115.J/mol*KPHPMSMeot-Ner, 1984, 2gas phase; M

Potassium ion (1+) + N,N-Dimethylacetamide = (Potassium ion (1+) • N,N-Dimethylacetamide)

By formula: K+ + C4H9NO = (K+ • C4H9NO)

Quantity Value Units Method Reference Comment
Δr121.kJ/molCIDTKlassen, Anderson, et al., 1996RCD
Δr130.kJ/molHPMSSunner, 1984gas phase; M
Quantity Value Units Method Reference Comment
Δr96.J/mol*KHPMSSunner, 1984gas phase; M

(Potassium ion (1+) • 2N,N-Dimethylacetamide) + N,N-Dimethylacetamide = (Potassium ion (1+) • 3N,N-Dimethylacetamide)

By formula: (K+ • 2C4H9NO) + C4H9NO = (K+ • 3C4H9NO)

Quantity Value Units Method Reference Comment
Δr75.kJ/molHPMSSunner, 1984gas phase; M
Quantity Value Units Method Reference Comment
Δr100.J/mol*KHPMSSunner, 1984gas phase; M

(Potassium ion (1+) • N,N-Dimethylacetamide) + N,N-Dimethylacetamide = (Potassium ion (1+) • 2N,N-Dimethylacetamide)

By formula: (K+ • C4H9NO) + C4H9NO = (K+ • 2C4H9NO)

Quantity Value Units Method Reference Comment
Δr100.kJ/molHPMSSunner, 1984gas phase; M
Quantity Value Units Method Reference Comment
Δr100.J/mol*KHPMSSunner, 1984gas phase; M

N,N-Dimethylacetamide = Ethanimidic acid, N-methyl-, methyl ester

By formula: C4H9NO = C4H9NO

Quantity Value Units Method Reference Comment
Δr67. ± 3.kJ/molEqkBeak, Lee, et al., 1978liquid phase; ALS

Sodium ion (1+) + N,N-Dimethylacetamide = (Sodium ion (1+) • N,N-Dimethylacetamide)

By formula: Na+ + C4H9NO = (Na+ • C4H9NO)

Quantity Value Units Method Reference Comment
Δr157.kJ/molCIDTKlassen, Anderson, et al., 1996RCD

Gas phase ion energetics data

Go To: Top, Reaction thermochemistry data, Ion clustering data, IR Spectrum, Mass spectrum (electron ionization), Gas Chromatography, References, Notes

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)908.0kJ/molN/AHunter and Lias, 1998HL
Quantity Value Units Method Reference Comment
Gas basicity877.0kJ/molN/AHunter and Lias, 1998HL

Ionization energy determinations

IE (eV) Method Reference Comment
9.20 ± 0.05EIBaldwin, Loudon, et al., 1977LLK
8.81CTSSlifkin and Allison, 1967RDSH
8.81 ± 0.03PIWatanabe, Nakayama, et al., 1962RDSH
9.43PESweigart and Turner, 1972Vertical value; LLK

Appearance energy determinations

Ion AE (eV) Other Products MethodReferenceComment
C2H3O+12.55?EILoudon and Webb, 1977LLK
C2H3O+11.4 ± 0.1?EIGowenlock, Jones, et al., 1961RDSH
C2H6N+12.15?EILoudon and Webb, 1977LLK
C2H6N+12.4 ± 0.1?EIGowenlock, Jones, et al., 1961RDSH
C3H6NO+11.60?EILoudon and Webb, 1977LLK

De-protonation reactions

C4H8NO- + Hydrogen cation = N,N-Dimethylacetamide

By formula: C4H8NO- + H+ = C4H9NO

Quantity Value Units Method Reference Comment
Δr1568. ± 8.8kJ/molG+TSBartmess, Scott, et al., 1979gas phase; value altered from reference due to change in acidity scale; B
Quantity Value Units Method Reference Comment
Δr1540. ± 8.4kJ/molIMREBartmess, Scott, et al., 1979gas phase; value altered from reference due to change in acidity scale; B

Ion clustering data

Go To: Top, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), Gas Chromatography, 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:
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. Searches may be limited to ion clustering reactions. A general reaction search form is also available.

Clustering reactions

C3H10N+ + N,N-Dimethylacetamide = (C3H10N+ • N,N-Dimethylacetamide)

By formula: C3H10N+ + C4H9NO = (C3H10N+ • C4H9NO)

Bond type: Hydrogen bonds of the type NH+-O between organics

Quantity Value Units Method Reference Comment
Δr114.kJ/molPHPMSMeot-Ner, 1984gas phase; M
Δr114.kJ/molPHPMSMeot-Ner, 1984, 2gas phase; M
Quantity Value Units Method Reference Comment
Δr101.J/mol*KPHPMSMeot-Ner, 1984gas phase; M
Δr101.J/mol*KPHPMSMeot-Ner, 1984, 2gas phase; M

C4H10NO+ + N,N-Dimethylacetamide = (C4H10NO+ • N,N-Dimethylacetamide)

By formula: C4H10NO+ + C4H9NO = (C4H10NO+ • C4H9NO)

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

Quantity Value Units Method Reference Comment
Δr131.kJ/molPHPMSMeot-Ner, 1984, 2gas phase; M
Quantity Value Units Method Reference Comment
Δr115.J/mol*KPHPMSMeot-Ner, 1984, 2gas phase; M

Potassium ion (1+) + N,N-Dimethylacetamide = (Potassium ion (1+) • N,N-Dimethylacetamide)

By formula: K+ + C4H9NO = (K+ • C4H9NO)

Quantity Value Units Method Reference Comment
Δr121.kJ/molCIDTKlassen, Anderson, et al., 1996RCD
Δr130.kJ/molHPMSSunner, 1984gas phase; M
Quantity Value Units Method Reference Comment
Δr96.J/mol*KHPMSSunner, 1984gas phase; M

(Potassium ion (1+) • N,N-Dimethylacetamide) + N,N-Dimethylacetamide = (Potassium ion (1+) • 2N,N-Dimethylacetamide)

By formula: (K+ • C4H9NO) + C4H9NO = (K+ • 2C4H9NO)

Quantity Value Units Method Reference Comment
Δr100.kJ/molHPMSSunner, 1984gas phase; M
Quantity Value Units Method Reference Comment
Δr100.J/mol*KHPMSSunner, 1984gas phase; M

(Potassium ion (1+) • 2N,N-Dimethylacetamide) + N,N-Dimethylacetamide = (Potassium ion (1+) • 3N,N-Dimethylacetamide)

By formula: (K+ • 2C4H9NO) + C4H9NO = (K+ • 3C4H9NO)

Quantity Value Units Method Reference Comment
Δr75.kJ/molHPMSSunner, 1984gas phase; M
Quantity Value Units Method Reference Comment
Δr100.J/mol*KHPMSSunner, 1984gas phase; M

Sodium ion (1+) + N,N-Dimethylacetamide = (Sodium ion (1+) • N,N-Dimethylacetamide)

By formula: Na+ + C4H9NO = (Na+ • C4H9NO)

Quantity Value Units Method Reference Comment
Δr157.kJ/molCIDTKlassen, Anderson, et al., 1996RCD

IR Spectrum

Go To: Top, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering data, Mass spectrum (electron ionization), Gas Chromatography, References, Notes

Data compiled by: Coblentz Society, Inc.

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


Mass spectrum (electron ionization)

Go To: Top, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering data, IR Spectrum, Gas Chromatography, 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

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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 NIST Mass Spectrometry Data Center, 1998.
NIST MS number 291288

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.


Gas Chromatography

Go To: Top, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering 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: NIST Mass Spectrometry Data Center, William E. Wallace, director

Kovats' RI, non-polar column, temperature ramp

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Column type Active phase I Reference Comment
CapillaryOV-101820.Ohnishi and Shibamoto, 19842. K/min; Column length: 50. m; Column diameter: 0.23 mm; Tstart: 80. C; Tend: 200. C

Van Den Dool and Kratz RI, non-polar column, temperature ramp

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Column type Active phase I Reference Comment
CapillarySPB-Sulfur833.3de Lacy Costello, Evans, et al., 200130. m/0.32 mm/4. μm, 40. C @ 12.5 min, 4. K/min; Tend: 200. C

Van Den Dool and Kratz RI, polar column, temperature ramp

View large format table.

Column type Active phase I Reference Comment
CapillaryDB-Wax1414.Shimoda, Shigematsu, et al., 199560. m/0.25 mm/0.25 μm, 2. K/min; Tstart: 50. C; Tend: 230. C

Normal alkane RI, non-polar column, temperature ramp

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Column type Active phase I Reference Comment
CapillaryOV-101833.Zenkevich, 200525. m/0.20 mm/0.10 μm, N2/He, 6. K/min; Tstart: 50. C; Tend: 250. C

Normal alkane RI, non-polar column, custom temperature program

View large format table.

Column type Active phase I Reference Comment
CapillaryDB-5 MS883.Luo and Agnew, 200130. m/0.25 mm/1.0 μm, Helium; Program: not specified
CapillarySPB-1835.Flanagan, Streete, et al., 199760. m/0.53 mm/5. μm, He; Program: 40C(6min) => 5C/min => 80C => 10C/min => 200C
CapillarySPB-1835.Strete, Ruprah, et al., 199260. m/0.53 mm/5.0 μm, Helium; Program: 40 0C (6 min) 5 0C/min -> 80 0C 10 0C/min -> 200 0C
CapillaryMethyl Silicone840.Zenkevich and Kuznetsova, 1990Program: not specified

Normal alkane RI, polar column, temperature ramp

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Column type Active phase I Reference Comment
CapillaryDB-Wax1437.Shimadzu, 201230. m/0.32 mm/0.50 μm, Helium, 4. K/min; Tstart: 40. C; Tend: 260. C
CapillaryDB-Wax1437.Shimadzu Corporation, 200330. m/0.32 mm/0.5 μm, He, 4. K/min; Tstart: 40. C; Tend: 260. C

Normal alkane RI, polar column, custom temperature program

View large format table.

Column type Active phase I Reference Comment
CapillaryDB-Wax1384.Peng, Yang, et al., 1991Program: not specified
CapillaryDB-Wax1409.Peng, Yang, et al., 1991Program: not specified

References

Go To: Top, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering 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.

Meot-Ner, 1984
Meot-Ner, (Mautner)M., The Ionic Hydrogen Bond and Ion Solvation. 1. -NH+ O-, -NH+ N- and -OH+ O- Bonds. Correlations with Proton Affinity. Deviations Due to Structural Effects, J. Am. Chem. Soc., 1984, 106, 5, 1257, https://doi.org/10.1021/ja00317a015 . [all data]

Meot-Ner, 1984, 2
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]

Bartmess, Scott, et al., 1979
Bartmess, J.E.; Scott, J.A.; McIver, R.T., Jr., The gas phase acidity scale from methanol to phenol, J. Am. Chem. Soc., 1979, 101, 6047. [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]

Sunner, 1984
Sunner, J. Kebarle, Ion - Solvent Molecule Interactions in the Gas Phase. The Potassium Ion and Me2SO, DMA, DMF, and Acetone, J. Am. Chem. Soc., 1984, 106, 21, 6135, https://doi.org/10.1021/ja00333a002 . [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]

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]

Baldwin, Loudon, et al., 1977
Baldwin, M.A.; Loudon, A.G.; Webb, K.S.; Cardnell, P.C., Charge location and fragmentation under electron impact. V-The ionization potentials of (methylated) phosphoramides, guanidines, formamides, acetamides, ureas and thioureas, Org. Mass Spectrom., 1977, 12, 279. [all data]

Slifkin and Allison, 1967
Slifkin, M.A.; Allison, A.C., Measurement of ionization potentials from contact charge transfer spectra, Nature, 1967, 215, 949. [all data]

Watanabe, Nakayama, et al., 1962
Watanabe, K.; Nakayama, T.; Mottl, J., Ionization potentials of some molecules, J. Quant. Spectry. Radiative Transfer, 1962, 2, 369. [all data]

Sweigart and Turner, 1972
Sweigart, D.A.; Turner, D.W., Lone pair orbitals and their interactions studied by photoelectron spectroscopy. I. Carboxylic acids and their derivatives, J. Am. Chem. Soc., 1972, 94, 5592. [all data]

Loudon and Webb, 1977
Loudon, A.G.; Webb, K.S., The nature of the [C2H6N]+ and [CH4N]+ ions formed by electron impact on methylated formamides, acetamides, ureas, thioureas and hexamethylphosphoramide, Org. Mass Spectrom., 1977, 12, 283. [all data]

Gowenlock, Jones, et al., 1961
Gowenlock, B.G.; Jones, P.P.; Majer, J.R., Bond dissociation energies in some molecules containing alkyl substituted CH3, NH2, and OH, J. Chem. Soc. Faraday Trans., 1961, 57, 23. [all data]

Ohnishi and Shibamoto, 1984
Ohnishi, S.; Shibamoto, T., Volatile compounds from heated beef fat and beef fat with glycine, J. Agric. Food Chem., 1984, 32, 5, 987-992, https://doi.org/10.1021/jf00125a008 . [all data]

de Lacy Costello, Evans, et al., 2001
de Lacy Costello, B.P.J.; Evans, P.; Ewen, R.J.; Gunson, H.E.; Jones, P.R.H.; Ratcliffe, N.M.; Spencer-Phillips, P.T.N., Gas chromatography-mass spectrometry analyses of volatile organic compounds from potato tubers inoculated with Phytophthora infestans or Fusarium coeruleum, Plant Pathol., 2001, 50, 4, 489-496, https://doi.org/10.1046/j.1365-3059.2001.00594.x . [all data]

Shimoda, Shigematsu, et al., 1995
Shimoda, M.; Shigematsu, H.; Shiratsuchi, H.; Osajima, Y., Comparison of the odor concentrates by SDE and adsorptive column method from green tea infusion, J. Agric. Food Chem., 1995, 43, 6, 1616-1620, https://doi.org/10.1021/jf00054a037 . [all data]

Zenkevich, 2005
Zenkevich, I.G., Experimentally measured retention indices., 2005. [all data]

Luo and Agnew, 2001
Luo, J.; Agnew, M.P., Gas characteristics before and after biofiltration treating odorous emissions from animal rendering processes, Environ. Technol., 2001, 22, 9, 1091-1103, https://doi.org/10.1080/09593332208618220 . [all data]

Flanagan, Streete, et al., 1997
Flanagan, R.J.; Streete, P.J.; Ramsey, J.D., Volatile Substance Abuse, UNODC Technical Series, No 5, United Nations, Office on Drugs and Crime, Vienna International Centre, PO Box 500, A-1400 Vienna, Austria, 1997, 56, retrieved from http://www.odccp.org/pdf/technicalseries1997-01-011.pdf. [all data]

Strete, Ruprah, et al., 1992
Strete, P.J.; Ruprah, M.; Ramsey, J.D.; Flanagan, R.J., Detection and identification of volatile substances by headspace capillary gas chromatography to aid the diagnosis of acute poisoning, Analyst, 1992, 117, 7, 1111-1127, https://doi.org/10.1039/an9921701111 . [all data]

Zenkevich and Kuznetsova, 1990
Zenkevich, I.G.; Kuznetsova, L.M., Logic Criteria on Prediction of Gas Chromatographic Retention Indices from Physico-Chemical Properties of Organic Compounds, Dokl. Akad. Nauk SSSR, 1990, 315, 4, 881-885. [all data]

Shimadzu, 2012
Shimadzu, Pharmaceutical Related, Analysis of pharmaceutical residual solvent (observation of separation) (1) - GC, 2012, retrieved from www.shimadzu.ru/applications/Applicationspdf/GC/Pharma/Pharmaceutical residual solvents GC.pdf. [all data]

Shimadzu Corporation, 2003
Shimadzu Corporation, Analysis of pharmaceutical residual solvent (observation of separation), 2003, retrieved from http://www.shimadzu.com.br/analitica/aplicacoes/book/pharm69.pdf. [all data]

Peng, Yang, et al., 1991
Peng, C.T.; Yang, Z.C.; Ding, S.F., Prediction of rentention idexes. II. Structure-retention index relationship on polar columns, J. Chromatogr., 1991, 586, 1, 85-112, https://doi.org/10.1016/0021-9673(91)80028-F . [all data]


Notes

Go To: Top, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering data, IR Spectrum, Mass spectrum (electron ionization), Gas Chromatography, References