Acetamide, N-methyl-
- Formula: C3H7NO
- Molecular weight: 73.0938
- IUPAC Standard InChIKey: OHLUUHNLEMFGTQ-UHFFFAOYSA-N
- CAS Registry Number: 79-16-3
- 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. - Other names: Methylacetamide; Monomethylacetamide; N-Methylacetamide; CH3CONHCH3; Acetylmethylamine; N-Acetyl-N-methylamine; X 44
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Gas phase ion energetics data
Go To: Top, 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
View reactions leading to C3H7NO+ (ion structure unspecified)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Proton affinity (review) | 212.4 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
Quantity | Value | Units | Method | Reference | Comment |
Gas basicity | 205.0 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
9.70 ± 0.05 | EI | Baldwin, Loudon, et al., 1977 | LLK |
8.90 ± 0.02 | PI | Watanabe, Nakayama, et al., 1962 | RDSH |
~9.85 | PE | Sweigart and Turner, 1972 | Vertical value; LLK |
Appearance energy determinations
Ion | AE (eV) | Other Products | Method | Reference | Comment |
---|---|---|---|---|---|
CH4N+ | 11.50 | ? | EI | Loudon and Webb, 1977 | LLK |
C2H3O+ | 12.40 | ? | EI | Loudon and Webb, 1977 | LLK |
C2H4NO+ | 11.80 | ? | EI | Loudon and Webb, 1977 | LLK |
De-protonation reactions
C3H6NO- + =
By formula: C3H6NO- + H+ = C3H7NO
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 361.8 ± 2.2 | kcal/mol | G+TS | Decouzon, Exner, et al., 1990 | gas phase; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 354.5 ± 2.0 | kcal/mol | IMRE | Decouzon, Exner, et al., 1990 | gas phase; B |
Ion clustering data
Go To: Top, 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:
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. Searches may be limited to ion clustering reactions. A general reaction search form is also available.
Clustering reactions
By formula: C2H3O2- + C3H7NO = (C2H3O2- • C3H7NO)
Bond type: Hydrogen bonds of deprotonated acids to amides
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 25.4 ± 1.0 | kcal/mol | TDAs | Meot-ner, 1988 | gas phase; B,M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 27.4 | cal/mol*K | PHPMS | Meot-Ner (Mautner), 1988 | gas phase; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 17.2 ± 1.0 | kcal/mol | TDAs | Meot-ner, 1988 | gas phase; B |
By formula: (C2H3O2- • C3H7NO) + C3H7NO = (C2H3O2- • 2C3H7NO)
Bond type: Hydrogen bonds of deprotonated acids to amides
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 17.6 | kcal/mol | PHPMS | Meot-Ner (Mautner), 1988 | gas phase; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 21.8 | cal/mol*K | PHPMS | Meot-Ner (Mautner), 1988 | gas phase; M |
By formula: C3H6NO- + C3H7NO = (C3H6NO- • C3H7NO)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 27. | kcal/mol | PHPMS | Meot-Ner (Mautner), 1988 | gas phase; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 30. | cal/mol*K | PHPMS | Meot-Ner (Mautner), 1988 | gas phase; M |
Free energy of reaction
ΔrG° (kcal/mol) | T (K) | Method | Reference | Comment |
---|---|---|---|---|
12.5 | 497. | PHPMS | Meot-Ner (Mautner), 1988 | gas phase; M |
By formula: C3H8NO+ + C3H7NO = (C3H8NO+ • C3H7NO)
Bond type: Hydrogen bonds of the type OH-O between organics
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 29.8 | kcal/mol | PHPMS | Meot-Ner, 1984 | gas phase; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 23.6 | cal/mol*K | PHPMS | Meot-Ner, 1984 | gas phase; M |
By formula: C4H4N- + C3H7NO = (C4H4N- • C3H7NO)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 27. | kcal/mol | PHPMS | Meot-Ner (Mautner), 1988 | gas phase; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 30. | cal/mol*K | PHPMS | Meot-Ner (Mautner), 1988 | gas phase; M |
Free energy of reaction
ΔrG° (kcal/mol) | T (K) | Method | Reference | Comment |
---|---|---|---|---|
11.9 | 497. | PHPMS | Meot-Ner (Mautner), 1988 | gas phase; M |
By formula: K+ + C3H7NO = (K+ • C3H7NO)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 30.4 | kcal/mol | CIDT | Klassen, Anderson, et al., 1996 | RCD |
By formula: Li+ + C3H7NO = (Li+ • C3H7NO)
Free energy of reaction
ΔrG° (kcal/mol) | T (K) | Method | Reference | Comment |
---|---|---|---|---|
41.4 | 373. | CIDT,ICR | Herreros, Gal, et al., 1999 | RCD |
By formula: Na+ + C3H7NO = (Na+ • C3H7NO)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 35.7 | kcal/mol | CIDT | Klassen, Anderson, et al., 1996 | RCD |
IR Spectrum
Go To: Top, Gas phase ion energetics data, Ion clustering data, 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 by: NIST Mass Spectrometry Data Center, William E. Wallace, director
Gas Phase Spectrum
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Notice: Concentration information is not available for this spectrum and, therefore, molar absorptivity values cannot be derived.
Additional Data
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Download spectrum in JCAMP-DX format.
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 |
Mass spectrum (electron ionization)
Go To: Top, 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
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 | Japan AIST/NIMC Database- Spectrum MS-NW-4322 |
NIST MS number | 230310 |
Gas Chromatography
Go To: Top, 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, isothermal
Column type | Active phase | Temperature (C) | I | Reference | Comment |
---|---|---|---|---|---|
Packed | SE-30 | 180. | 857. | Krawczyk and Piotrowski, 1989 | N2, Chromosorb W AW; Column length: 1. m |
Van Den Dool and Kratz RI, polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | DB-Wax | 1623. | Shiratsuchi, Shimoda, et al., 1994 | 60. m/0.25 mm/0.25 μm, 2. K/min, 230. C @ 60. min; Tstart: 50. C |
Capillary | DB-Wax | 1623. | Shiratsuchi, Shimoda, et al., 1994, 2 | 60. m/0.25 mm/0.25 μm, He, 2. K/min, 230. C @ 60. min; Tstart: 50. C |
Normal alkane RI, non-polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | Polydimethyl siloxanes | 825. | Zenkevich and Chupalov, 1996 | Program: not specified |
Normal alkane RI, polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | DB-Wax | 1609. | Peng, Yang, et al., 1991 | Program: not specified |
Capillary | DB-Wax | 1648. | Peng, Yang, et al., 1991 | Program: not specified |
References
Go To: Top, 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.
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]
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]
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]
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]
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]
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]
Krawczyk and Piotrowski, 1989
Krawczyk, W.; Piotrowski, G.T.,
Relationships Between Structure and Retention Index for N-Substituted Amides of Aliphatic Acids on a Non-Polar Column,
J. Chromatogr., 1989, 463, 297-304, https://doi.org/10.1016/S0021-9673(01)84484-8
. [all data]
Shiratsuchi, Shimoda, et al., 1994
Shiratsuchi, H.; Shimoda, M.; Imayoshi, K.; Noda, K.; Osajima, Y.,
Off-flavor compounds in spray-dried skim milk powder,
J. Agric. Food Chem., 1994, 42, 6, 1323-1327, https://doi.org/10.1021/jf00042a014
. [all data]
Shiratsuchi, Shimoda, et al., 1994, 2
Shiratsuchi, H.; Shimoda, M.; Imayoshi, K.; Noda, K.; Osajima, Y.,
Volatile flavor compounds in spray-dried skim milk powder,
J. Agric. Food Chem., 1994, 42, 4, 984-988, https://doi.org/10.1021/jf00040a028
. [all data]
Zenkevich and Chupalov, 1996
Zenkevich, I.G.; Chupalov, A.A.,
New Possibilities of Chromato Mass Pectrometric Identification of Organic Compounds Using Increments of Gas Chromatographic Retention Indices of Molecular Structural Fragments,
Zh. Org. Khim. (Rus.), 1996, 32, 5, 656-666. [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, Gas phase ion energetics data, Ion clustering data, IR Spectrum, Mass spectrum (electron ionization), Gas Chromatography, References
- Symbols used in this document:
AE Appearance energy T Temperature ΔrG° Free energy of reaction at standard conditions ΔrH° Enthalpy of reaction at standard conditions ΔrS° Entropy of reaction at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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