N-Allyl-N,N-dimethylamine
- Formula: C5H11N
- Molecular weight: 85.1475
- IUPAC Standard InChI: InChI=1S/C5H11N/c1-4-5-6(2)3/h4H,1,5H2,2-3H3
- IUPAC Standard InChIKey: GBCKRQRXNXQQPW-UHFFFAOYSA-N
- CAS Registry Number: 2155-94-4
- 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: CH2=CHCH2N(CH3)2; N,N-Dimethylallylamine; Allyldimethylamine; N-Allyldimethylamine; 2-Propen-1-amine, N,N-dimethyl-; Allylamine, N,N-dimethyl-; Dimethylallylamine; N,N-Dimethyl-2-propene-1-amine
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Gas phase ion energetics data
Go To: Top, 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
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| Proton affinity (review) | 228.9 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
| Quantity | Value | Units | Method | Reference | Comment |
| Gas basicity | 221.5 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
Ionization energy determinations
| IE (eV) | Method | Reference | Comment |
|---|---|---|---|
| 7.84 ± 0.03 | PI | Loguinov, Takhistov, et al., 1981 | LLK |
| 7.84 | PI | Akopyan, Vilesov, et al., 1975 | LLK |
| 7.84 ± 0.05 | PE | Akopyan and Loginov, 1974 | LLK |
Appearance energy determinations
| Ion | AE (eV) | Other Products | Method | Reference | Comment |
|---|---|---|---|---|---|
| C2H6N+ | 8.58 | C3H5 | PI | Akopyan, Vilesov, et al., 1975 | LLK |
| C3H5+ | 9.55 | C2H6N | PI | Akopyan, Vilesov, et al., 1975 | LLK |
| C3H6+ | 9.58 | C2H5N | PI | Akopyan, Vilesov, et al., 1975 | LLK |
| C3H8N+ | 9.55 ± 0.05 | C2H3 | PI | Loguinov, Takhistov, et al., 1981 | LLK |
| C3H8N+ | 9.55 | C2H3 | PI | Akopyan, Vilesov, et al., 1975 | LLK |
| C4H8N+ | 9.62 | CH3 | PI | Akopyan, Vilesov, et al., 1975 | LLK |
| C5H10N+ | 9.56 | H | PI | Akopyan, Vilesov, et al., 1975 | LLK |
De-protonation reactions
C5H10N- + =
By formula: C5H10N- + H+ = C5H11N
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 388.6 ± 4.1 | kcal/mol | G+TS | Dahlke and Kass, 1991 | gas phase; Between H2O, furan. Reprotonation site uncertain; B |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrG° | 382.0 ± 4.0 | kcal/mol | IMRB | Dahlke and Kass, 1991 | gas phase; Between H2O, furan. Reprotonation site uncertain; B |
Gas Chromatography
Go To: Top, Gas phase ion energetics data, 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
Normal alkane RI, non-polar column, temperature ramp
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | OV-101 | 604. | Zenkevich, 2005 | 25. m/0.20 mm/0.10 μm, N2/He, 6. K/min; Tstart: 50. C; Tend: 250. C |
References
Go To: Top, Gas phase ion energetics data, 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]
Loguinov, Takhistov, et al., 1981
Loguinov, Y.; Takhistov, V.V.; Vatlina, L.P.,
Photoionization studies of substituted trimethylamines,
Org. Mass Spectrom., 1981, 16, 239. [all data]
Akopyan, Vilesov, et al., 1975
Akopyan, M.E.; Vilesov, F.I.; Loginov, Y.V.,
Photoionization of amines and the monomolecular decomposition of excited molecular ions,
Khim. Vys. Energ., 1975, 9, 327. [all data]
Akopyan and Loginov, 1974
Akopyan, M.E.; Loginov, Yu.V.,
Photoelectron spectra of trimethylamine derivatives,
Opt. Spectrosc., 1974, 37, 250, In original 442. [all data]
Dahlke and Kass, 1991
Dahlke, G.D.; Kass, S.R.,
Substituent Effects in the Gas Phase - 1-Substituted Allyl Anions,
J. Am. Chem. Soc., 1991, 113, 15, 5566, https://doi.org/10.1021/ja00015a008
. [all data]
Zenkevich, 2005
Zenkevich, I.G.,
Experimentally measured retention indices., 2005. [all data]
Notes
Go To: Top, Gas phase ion energetics data, Gas Chromatography, References
- Symbols used in this document:
AE Appearance 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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