2,4(1H,3H)-Pyrimidinedione, 1,3-dimethyl-
- Formula: C6H8N2O2
- Molecular weight: 140.1399
- IUPAC Standard InChI: InChI=1S/C6H8N2O2/c1-7-4-3-5(9)8(2)6(7)10/h3-4H,1-2H3
- IUPAC Standard InChIKey: JSDBKAHWADVXFU-UHFFFAOYSA-N
- CAS Registry Number: 874-14-6
- Chemical structure:
This structure is also available as a 2d Mol file - Other names: Uracil, 1,3-dimethyl-; N,N'-Dimethyluracil; N1,N3-Dimethyluracil; 1,3-Dimethyluracil; 2,4-Dihydroxy-1,3-dimethylpyrimidine
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Gas phase thermochemistry data
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: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔfH°gas | -74.95 ± 0.36 | kcal/mol | Ccr | Imamura, Takahashi, et al., 1989 |
Gas phase ion energetics data
Go To: Top, Gas 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 compiled as indicated in comments:
B - John E. Bartmess
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
Electron affinity determinations
| EA (eV) | Reference | Comment |
|---|---|---|
| 0.04 ± 0.10 | Desfrancois, Abdoul-Carime, et al., 1999 | B |
Ionization energy determinations
| IE (eV) | Method | Reference | Comment |
|---|---|---|---|
| 8.8 ± 0.1 | EI | Verkin, Sukodub, et al., 1976 | LLK |
| 9.00 | PE | Dougherty, Wittel, et al., 1976 | Vertical value; LLK |
De-protonation reactions
C6H7N2O2- + =
By formula: C6H7N2O2- + H+ = C6H8N2O2
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 369.0 ± 2.0 | kcal/mol | IMRB | Lee, 2005 | gas phase; B |
| ΔrH° | 370.7 ± 3.2 | kcal/mol | G+TS | Gronert, Feng, et al., 2000 | gas phase; B |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrG° | 363.0 ± 3.1 | kcal/mol | IMRB | Gronert, Feng, et al., 2000 | gas phase; B |
C6H7N2O2- + =
By formula: C6H7N2O2- + H+ = C6H8N2O2
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 384.0 ± 3.0 | kcal/mol | IMRB | Lee, 2005 | gas phase; B |
References
Go To: Top, Gas 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.
Imamura, Takahashi, et al., 1989
Imamura, A.; Takahashi, K.; Murata, S.; Sakiyama, M.,
Standard enthalpies of formation of trimethyl cyanurate, malonamide, and 1,3-dimethyluracil,
J. Chem. Thermodyn., 1989, 21, 237-246. [all data]
Desfrancois, Abdoul-Carime, et al., 1999
Desfrancois, C.; Abdoul-Carime, H.; Carles, S.; Periquet, V.; Schermann, J.P.; Smith, D.M.A.; Adamowicz, L.,
Experimental and theoretical ab initio study of the influence of N-methylation on the dipole-bound electron affinities of thymine and uracil,
J. Chem. Phys., 1999, 110, 24, 11876-11883, https://doi.org/10.1063/1.479175
. [all data]
Verkin, Sukodub, et al., 1976
Verkin, B.I.; Sukodub, L.F.; Yanson, I.K.,
Ionization potentials of nitrogenous bases of of nucleic acids,
Dokl. Akad. Nauk SSSR, 1976, 228, 1452. [all data]
Dougherty, Wittel, et al., 1976
Dougherty, D.; Wittel, K.; Meeks, J.; McGlynn, S.P.,
Photoelectron spectroscopy of carbonyls. Ureas, uracils, and thymine,
J. Am. Chem. Soc., 1976, 98, 3815. [all data]
Lee, 2005
Lee, J.K.,
Insights into nucleic acid reactivity through gas-phase experimental and computational studies,
Int. J. Mass Spectrom., 2005, 240, 3, 261-272, https://doi.org/10.1016/j.ijms.2004.09.020
. [all data]
Gronert, Feng, et al., 2000
Gronert, S.; Feng, W.Y.; Chew, F.; Wu, W.M.,
The gas phase acid/base properties of 1,3,-dimethyluracil, 1-methyl-2-pyridone, and 1-methyl-4-pyridone: relevance to the mechanism of orotidine-5 '-monophosphate decarboxylase,
Int. J. Mass Spectrom., 2000, 196, 251-258, https://doi.org/10.1016/S1387-3806(99)00191-8
. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Gas phase ion energetics data, References
- Symbols used in this document:
EA Electron affinity ΔfH°gas Enthalpy of formation of gas 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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