Formamide, N,N-dimethyl-
- Formula: C3H7NO
- Molecular weight: 73.0938
- IUPAC Standard InChIKey: ZMXDDKWLCZADIW-UHFFFAOYSA-N
- CAS Registry Number: 68-12-2
- 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: Dimethylformamide; DMF; DMF (amide); DMFA; N-Formyldimethylamine; N,N-Dimethylformamide; HCON(CH3)2; Formyldimethylamine; Dimethylforamide; Dimethylformamid; Dimetilformamide; Dwumetyloformamid; N,N-Dimethylmethanamide; NSC-5356; U-4224; Dimethylamid kyseliny mravenci; Dimetylformamidu; NCI-C60913; UN 2265; DMF (dimethylformamide); N,N-Dimethylformaldehyde
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Gas phase ion energetics data
Go To: Top, 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
L - Sharon G. Lias
Data compiled as indicated in comments:
B - John E. Bartmess
LBLHLM - Sharon G. Lias, John E. Bartmess, Joel F. Liebman, John L. Holmes, Rhoda D. Levin, and W. Gary Mallard
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 |
---|---|---|---|---|---|
IE (evaluated) | 9.13 | eV | N/A | N/A | L |
Quantity | Value | Units | Method | Reference | Comment |
Proton affinity (review) | 887.5 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
Quantity | Value | Units | Method | Reference | Comment |
Gas basicity | 856.6 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
Electron affinity determinations
EA (eV) | Reference | Comment |
---|---|---|
0.01362 | Desfrancois, Periquet, et al., 1999 | B |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
9.45 ± 0.05 | EI | Baldwin, Loudon, et al., 1977 | LLK |
9.14 | PE | Brundle, Turner, et al., 1969 | RDSH |
9.12 ± 0.02 | PI | Watanabe, Nakayama, et al., 1962 | RDSH |
9.14 | PE | Bieri, Asbrink, et al., 1982 | Vertical value; LBLHLM |
9.25 | PE | Henriksen, Isaksson, et al., 1981 | Vertical value; LLK |
Appearance energy determinations
Ion | AE (eV) | Other Products | Method | Reference | Comment |
---|---|---|---|---|---|
CHO+ | 14.50 | ? | EI | Loudon and Webb, 1977 | LLK |
CHO+ | 14.3 ± 0.1 | ? | EI | Gowenlock, Jones, et al., 1961 | RDSH |
C2H6N+ | 11.60 | ? | EI | Loudon and Webb, 1977 | LLK |
C2H6N+ | 11.6 ± 0.1 | ? | EI | Gowenlock, Jones, et al., 1961 | RDSH |
C3H6NO+ | 11.35 | ? | EI | Loudon and Webb, 1977 | LLK |
De-protonation reactions
C3H6NO- + =
By formula: C3H6NO- + H+ = C3H7NO
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 1670. ± 17. | kJ/mol | G+TS | DePuy, Grabowski, et al., 1985 | gas phase; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 1640. ± 17. | kJ/mol | IMRB | DePuy, Grabowski, et al., 1985 | gas phase; B |
Mass spectrum (electron ionization)
Go To: Top, Gas phase ion energetics data, 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, 1990. |
NIST MS number | 118531 |
Gas Chromatography
Go To: Top, Gas phase ion energetics 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
Kovats' RI, non-polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | CBP-1 | 752. | Shimadzu, 2003 | 25. m/0.2 mm/0.25 μm, He, 50. C @ 5. min, 4. K/min; Tend: 200. C |
Kovats' RI, polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | CBP-20 | 1333. | Shimadzu, 2003 | 25. m/0.2 mm/0.25 μm, He, 50. C @ 5. min, 4. K/min; Tend: 200. C |
Capillary | Carbowax 20M | 1304. | Nishimura, Yamaguchi, et al., 1989 | 2. K/min; Column length: 50. m; Column diameter: 0.22 mm; Tstart: 80. C; Tend: 200. C |
Van Den Dool and Kratz RI, non-polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | SPB-Sulfur | 756.3 | de Lacy Costello, Evans, et al., 2001 | 30. 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
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | Supelcowax-10 | 1326. | Chung, Yung, et al., 2002 | 60. m/0.25 mm/0.25 μm, He, 35. C @ 5. min, 2. K/min, 195. C @ 90. min |
Capillary | Supelcowax-10 | 1326. | Chung, Yung, et al., 2001 | 60. m/0.25 mm/0.25 μm, He, 35. C @ 5. min, 2. K/min, 195. C @ 90. min |
Capillary | Supelcowax-10 | 1328. | Chung and Cadwallader, 1993 | 60. m/0.25 mm/0.25 μm, He, 40. C @ 5. min, 2. K/min, 195. C @ 40. min |
Capillary | DB-Wax | 1319. | Umano, Hagi, et al., 1992 | He, 40. C @ 10. min, 2. K/min; Column length: 30. m; Column diameter: 0.25 mm; Tend: 200. C |
Capillary | DB-Wax | 1282. | Frohlich and Schreier, 1990 | 30. m/0.32 mm/0.25 μm, He, 40. C @ 3. min, 5. K/min; Tend: 220. C |
Normal alkane RI, non-polar column, isothermal
Column type | Active phase | Temperature (C) | I | Reference | Comment |
---|---|---|---|---|---|
Capillary | Methyl Silicone | 100. | 747. | Lebrón-Aguilar, Quintanilla-López, et al., 2007 | |
Capillary | Methyl Silicone | 120. | 750. | Lebrón-Aguilar, Quintanilla-López, et al., 2007 | |
Capillary | Methyl Silicone | 140. | 753. | Lebrón-Aguilar, Quintanilla-López, et al., 2007 | |
Capillary | Methyl Silicone | 80. | 745. | Lebrón-Aguilar, Quintanilla-López, et al., 2007 | |
Capillary | DB-1 | 60. | 742. | Shimadzu, 2003, 2 | 60. m/0.32 mm/1. μm, He |
Packed | DC-400 | 150. | 790. | Anderson, 1968 | Helium, Gas-Pak (60-80 mesh); Column length: 3.0 m |
Normal alkane RI, non-polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | HP-5 MS | 772. | Radulovic, Blagojevic, et al., 2010 | 30. m/0.25 mm/0.25 μm, Helium, 5. K/min, 290. C @ 10. min; Tstart: 70. C |
Capillary | VF-5 | 783. | Li and Zhao, 2009 | 30. m/0.25 mm/0.25 μm, Helium, 60. C @ 2. min, 10. K/min, 300. C @ 10. min |
Normal alkane RI, non-polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | SPB-1 | 746. | Flanagan, Streete, et al., 1997 | 60. m/0.53 mm/5. μm, He; Program: 40C(6min) => 5C/min => 80C => 10C/min => 200C |
Capillary | Methyl Silicone | 751. | Zenkevich, Korolenko, et al., 1995 | Program: not specified |
Capillary | SPB-1 | 746. | Strete, Ruprah, et al., 1992 | 60. m/0.53 mm/5.0 μm, Helium; Program: 40 0C (6 min) 5 0C/min -> 80 0C 10 0C/min -> 200 0C |
Capillary | DB-1 | 735. | Kawai, Ishida, et al., 1991 | 60. m/0.25 mm/0.25 μm; Program: not specified |
Capillary | DB-1 | 738. | Kawai, Ishida, et al., 1991 | 60. m/0.25 mm/0.25 μm; Program: not specified |
Capillary | CP Sil 8 CB | 782. | Weller and Wolf, 1989 | 40. m/0.25 mm/0.25 μm, He; Program: 30 0C (1 min) 15 0C/min -> 45 0C 3 0C/min -> 120 0C |
Normal alkane RI, polar column, isothermal
Column type | Active phase | Temperature (C) | I | Reference | Comment |
---|---|---|---|---|---|
Capillary | DB-Wax | 60. | 1344. | Shimadzu, 2003, 2 | 50. m/0.32 mm/1. μm, He |
Normal alkane RI, polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | DB-Wax | 1361. | Shimadzu, 2012 | 30. m/0.32 mm/0.50 μm, Helium, 4. K/min; Tstart: 40. C; Tend: 260. C |
Capillary | DB-Wax | 1361. | Shimadzu Corporation, 2003 | 30. m/0.32 mm/0.5 μm, He, 4. K/min; Tstart: 40. C; Tend: 260. C |
Capillary | PEG-20M | 1295. | Kubota, Matsujage, et al., 1996 | 50. m/0.25 mm/0.25 μm, Nitrogen, 2. K/min; Tstart: 60. C; Tend: 180. C |
Normal alkane RI, polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | Polyethylene Glycol | 1325. | Zenkevich, Korolenko, et al., 1995 | Program: not specified |
Capillary | DB-Wax | 1312. | Peng, Yang, et al., 1991 | Program: not specified |
Capillary | DB-Wax | 1327. | Peng, Yang, et al., 1991 | Program: not specified |
Capillary | CP-Wax 52CB | 1290. | Vernin, 1991 | Column length: 50. m; Column diameter: 0.32 mm; Program: not specified |
Capillary | Superox 0.6; Carbowax 20M | 1276. | Waggott and Davies, 1984 | Hydrogen; Column length: 50. m; Column diameter: 0.32 mm; Program: not specified |
Capillary | Carbowax 400, Carbowax 20M, Carbowax 1540, Carbowax 4000, Superox 06, PEG 20M, etc. | 1276. | Waggott and Davies, 1984 | Hydrogen; Column length: 50. m; Column diameter: 0.32 mm; Program: not specified |
References
Go To: Top, Gas phase ion energetics data, 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,
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Desfrancois, Periquet, et al., 1999
Desfrancois, C.; Periquet, V.; Carles, S.; Schermann, J.P.; Smith, D.M.A.; Adamowicz, L.,
Experimental and ab initio theoretical studies of electron binding to formamide, N-methylformamide, and N,N-dimethylformamide.,
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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,
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Brundle, Turner, et al., 1969
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Photoelectron spectroscopy of simple amides and carboxylic acids,
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Watanabe, K.; Nakayama, T.; Mottl, J.,
Ionization potentials of some molecules,
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Bieri, Asbrink, et al., 1982
Bieri, G.; Asbrink, L.; Von Niessen, W.,
30.4-nm He(II) photoelectron spectra of organic molecules,
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Henriksen, Isaksson, et al., 1981
Henriksen, L.; Isaksson, R.; Liljefors, T.; Sandstrom, J.,
Ultraviolet absorption and photoelectron spectra of some cyclic and open-chain mono- and dithiooxamides,
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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,
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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,
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DePuy, Grabowski, et al., 1985
DePuy, C.H.; Grabowski, J.J.; Bierbaum, V.M.; Ingemann, S.; Nibbering, N.M.M.,
Gas-phase reactions of anions with methyl formate and N,N-dimethylformamide,
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Shimadzu, 2003
Shimadzu,
Gas chromatography analysis of organic solvents using capillary columns (No. 2), 2003, retrieved from http://www.shimadzu.com/apps/form.cfm. [all data]
Nishimura, Yamaguchi, et al., 1989
Nishimura, O.; Yamaguchi, K.; Mihara, S.; Shibamoto, T.,
Volatile Constituents of Guava Fruits (Psidium guajava L.) and Canned Puree,
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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,
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Comparison of volatile components in dried scallops (Chlamys farreri and Patinopecten yessoensis) prepared by boiling and steaming methods,
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Volatile components in blue crab (Callinectes sapidus) meat and processing by-product,
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Umano, Hagi, et al., 1992
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Volatile constituents of green and ripened pineapple (Aanas comosus [L.] Merr.),
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Frohlich and Schreier, 1990
Frohlich, O.; Schreier, P.,
Volatile Constituents of Loquat (Eriobotrya japonica Lindl.) Fruit,
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Lebrón-Aguilar, Quintanilla-López, et al., 2007
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Isothermal retention indices on poly (3,3,3-trifluoropropylmethylsiloxane) stationary phases,
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Shimadzu, 2003, 2
Shimadzu,
Gas chromatography analysis of organic solvents using capillary columns (No. 3), 2003, retrieved from http://www.shimadzu.com/apps/form.cfm. [all data]
Anderson, 1968
Anderson, D.G.,
USe of Kovats retention indices and response factors for the qualitative and quantitative analysis of coating solvents,
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Radulovic, Blagojevic, et al., 2010
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Comparative study of the leaf volatiles of Arctostaphylos uva-ursi (L.) Spreng. and Vaccinium vitis-idaea L. (Ericaceae),
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Vernin, G.,
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Notes
Go To: Top, Gas phase ion energetics data, Mass spectrum (electron ionization), Gas Chromatography, References
- Symbols used in this document:
AE Appearance energy EA Electron affinity IE (evaluated) Recommended ionization energy ΔrG° Free energy of reaction at standard conditions ΔrH° Enthalpy of reaction at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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