Propanamide, 2,2-dimethyl-
- Formula: C5H11NO
- Molecular weight: 101.1469
- IUPAC Standard InChIKey: XIPFMBOWZXULIA-UHFFFAOYSA-N
- CAS Registry Number: 754-10-9
- 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: Pivalamide; Trimethylacetamide
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Gas phase thermochemistry data
Go To: Top, Condensed phase thermochemistry data, 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: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°gas | -74.83 ± 0.33 | kcal/mol | Ccr | Abboud, Jimenez, et al., 1989 |
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 as indicated in comments:
DH - Eugene S. Domalski and Elizabeth D. Hearing
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°solid | -95.53 ± 0.31 | kcal/mol | Ccr | Abboud, Jimenez, et al., 1989 | ALS |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°solid | -750.45 ± 0.29 | kcal/mol | Ccr | Abboud, Jimenez, et al., 1989 | ALS |
Constant pressure heat capacity of liquid
Cp,liquid (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
38.19 | 298.150 | Abboud, Jimenez, et al., 1989 | One temperature; Cp given as 1.58 J/g*K.; DH |
Gas phase ion energetics data
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, 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
MM - Michael M. Meot-Ner (Mautner)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Proton affinity (review) | 212.5 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
Quantity | Value | Units | Method | Reference | Comment |
Gas basicity | 204.9 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
Gas basicity at 298K
Gas basicity (review) (kcal/mol) | Reference | Comment |
---|---|---|
204. ± 1. | Witt and Grutzmacher, 1997 | aniline; ortho-toluidine. Data readjusted to Hunter and Lias, 1998; MM |
205. ± 2. | Witt and Grutzmacher, 1997 | MM |
De-protonation reactions
C5H10NO- + =
By formula: C5H10NO- + H+ = C5H11NO
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 358.1 ± 2.1 | kcal/mol | G+TS | Taft, 1987 | gas phase; value altered from reference due to change in acidity scale; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 351.1 ± 2.0 | kcal/mol | IMRE | Taft, 1987 | gas phase; value altered from reference due to change in acidity scale; B |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Gas phase ion energetics data, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Abboud, Jimenez, et al., 1989
Abboud, J.-L.M.; Jimenez, P.; Roux, M.V.; Turrion, C.; Lopez-Mardomingo, C.,
Structural effects on the thermochemical properties of carbonyl compounds. I. Enthalpies of combustion, vapour pressures and enthalpies of sublimation, and enthalpies of formation of 2-methylpropanamide, 2,2-dimethylpropanamide, and 1-adamantyl carboxamide,
J. Chem. Thermodyn., 1989, 21, 859-865. [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]
Witt and Grutzmacher, 1997
Witt, M.; Grutzmacher, H.F.,
Proton-bound dimers of aliphatic carboxamides: gas-phase basicity and dissociation energy,
Int. J. Mass Spectrom. Ion Processes, 1997, 165, 49. [all data]
Taft, 1987
Taft, R.W.,
The Nature and Analysis of Substitutent Electronic Effects,
Personal communication. See also Prog. Phys. Org. Chem., 1987, 16, 1. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Gas phase ion energetics data, References
- Symbols used in this document:
Cp,liquid Constant pressure heat capacity of liquid ΔcH°solid Enthalpy of combustion of solid at standard conditions ΔfH°gas Enthalpy of formation of gas at standard conditions ΔfH°solid Enthalpy of formation of solid at standard conditions 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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