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2,4(1H,3H)-Pyrimidinedione, 1,3-dimethyl-

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Gas phase thermochemistry data

Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, 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: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Quantity Value Units Method Reference Comment
Deltafgas-313.6 ± 1.5kJ/molCcrImamura, Takahashi, 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:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DH - Eugene S. Domalski and Elizabeth D. Hearing

Quantity Value Units Method Reference Comment
Deltafsolid-410.5 ± 0.9kJ/molCcrImamura, Takahashi, et al., 1989ALS
Quantity Value Units Method Reference Comment
Deltacsolid-3093.87 ± 0.29kJ/molCcrImamura, Takahashi, et al., 1989ALS

Constant pressure heat capacity of solid

Cp,solid (J/mol*K) Temperature (K) Reference Comment
170.298.15Imamura, Takahashi, et al., 1989One temperature, estimated.; DH

Phase change data

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Reaction thermochemistry data, 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 as indicated in comments:
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Kenneth Kroenlein director
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
AC - William E. Acree, Jr., James S. Chickos
DH - Eugene S. Domalski and Elizabeth D. Hearing

Quantity Value Units Method Reference Comment
Tfus392.5KN/AZielenkiewicz, Zielenkiewicz, et al., 1984Uncertainty assigned by TRC = 0.5 K; TRC
Quantity Value Units Method Reference Comment
Deltavap71. ± 3.kJ/molVBeak and White, 1982ALS
Quantity Value Units Method Reference Comment
Deltasub96.9 ± 1.2kJ/molCImamura, Takahashi, et al., 1989ALS
Deltasub96.4 ± 1.4kJ/molCMurata, Sakiyama, et al., 1985AC
Deltasub92.kJ/molVClark, Peschel, et al., 1965ALS

Enthalpy of sublimation

DeltasubH (kJ/mol) Temperature (K) Method Reference Comment
96.900298.15N/AImamura, Takahashi, et al., 1989DH
115.8 ± 3.0338.TEBrunetti, Piacente, et al., 2000Based on data from 311. - 367. K.; AC
101.7 ± 2.1338.QRTeplitsky, Yanson, et al., 1980Based on data from 313. - 363. K.; AC
46. ± 4.2426.HASNowak, Szczepaniak, et al., 1978Based on data from 400. - 454. K.; AC
92.344. - 370.HASClark, Peschel, et al., 1965, 2AC

Entropy of sublimation

DeltasubS (J/mol*K) Temperature (K) Reference Comment
325.0298.15Imamura, Takahashi, et al., 1989DH

Enthalpy of fusion

DeltafusH (kJ/mol) Temperature (K) Reference Comment
23.100392.5Zielenkiewicz, Zielenkiewicz, et al., 1984, 2DH
14.6398.Domalski and Hearing, 1996AC

Entropy of fusion

DeltafusS (J/mol*K) Temperature (K) Reference Comment
58.9392.5Zielenkiewicz, Zielenkiewicz, et al., 1984, 2DH

Enthalpy of phase transition

DeltaHtrs (kJ/mol) Temperature (K) Initial Phase Final Phase Reference Comment
18.400394.crystaline, IIliquidSakiyama and Imamura, 1989Melting of the metastable phase.; DH
14.600398.crystaline, IliquidSakiyama and Imamura, 1989Melting of the stable phase.; DH

In addition to the Thermodynamics Research Center (TRC) data available from this site, much more physical and chemical property data is available from the following TRC products:


Reaction thermochemistry data

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, 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 as indicated in comments:
B - John E. Bartmess
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Note: Please consider using the reaction search for this species. This page allows searching of all reactions involving this species. A general reaction search form is also available. Future versions of this site may rely on reaction search pages in place of the enumerated reaction displays seen below.

Individual Reactions

C6H7N2O2- + Hydrogen cation = 2,4(1H,3H)-Pyrimidinedione, 1,3-dimethyl-

By formula: C6H7N2O2- + H+ = C6H8N2O2

Quantity Value Units Method Reference Comment
Deltar1544. ± 8.4kJ/molIMRBLee, 2005gas phase; B
Deltar1551. ± 13.kJ/molG+TSGronert, Feng, et al., 2000gas phase; B
Quantity Value Units Method Reference Comment
Deltar1519. ± 13.kJ/molIMRBGronert, Feng, et al., 2000gas phase; B

2,4-Dimethoxypyrimidine = 2,4(1H,3H)-Pyrimidinedione, 1,3-dimethyl-

By formula: C6H8N2O2 = C6H8N2O2

Quantity Value Units Method Reference Comment
Deltar-180. ± 13.kJ/molCisoBeak and White, 1982liquid phase; ALS
Deltar-160. ± 20.kJ/molCisoBeak and White, 1982gas phase; ALS

4-Methoxy-1-methyl-2-pyrimidinone = 2,4(1H,3H)-Pyrimidinedione, 1,3-dimethyl-

By formula: C6H8N2O2 = C6H8N2O2

Quantity Value Units Method Reference Comment
Deltar-104. ± 5.4kJ/molCisoBeak and White, 1982liquid phase; ALS
Deltar-110. ± 17.kJ/molCisoBeak and White, 1982gas phase; ALS

C6H7N2O2- + Hydrogen cation = 2,4(1H,3H)-Pyrimidinedione, 1,3-dimethyl-

By formula: C6H7N2O2- + H+ = C6H8N2O2

Quantity Value Units Method Reference Comment
Deltar1607. ± 13.kJ/molIMRBLee, 2005gas phase; B

Gas phase ion energetics data

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry 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 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 ± 0.10Desfrancois, Abdoul-Carime, et al., 1999B

Ionization energy determinations

IE (eV) Method Reference Comment
8.8 ± 0.1EIVerkin, Sukodub, et al., 1976LLK
9.00PEDougherty, Wittel, et al., 1976Vertical value; LLK

De-protonation reactions

C6H7N2O2- + Hydrogen cation = 2,4(1H,3H)-Pyrimidinedione, 1,3-dimethyl-

By formula: C6H7N2O2- + H+ = C6H8N2O2

Quantity Value Units Method Reference Comment
Deltar1544. ± 8.4kJ/molIMRBLee, 2005gas phase; B
Deltar1551. ± 13.kJ/molG+TSGronert, Feng, et al., 2000gas phase; B
Quantity Value Units Method Reference Comment
Deltar1519. ± 13.kJ/molIMRBGronert, Feng, et al., 2000gas phase; B

C6H7N2O2- + Hydrogen cation = 2,4(1H,3H)-Pyrimidinedione, 1,3-dimethyl-

By formula: C6H7N2O2- + H+ = C6H8N2O2

Quantity Value Units Method Reference Comment
Deltar1607. ± 13.kJ/molIMRBLee, 2005gas phase; B

Mass spectrum (electron ionization)

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction 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: 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 Japan AIST/NIMC Database- Spectrum MS-NW-2278
NIST MS number 227779

All mass spectra in this site (plus many more) are available from the NIST/EPA/NIH Mass Spectral Library. Please see the following for information about the library and its accompanying search program.


References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Mass spectrum (electron ionization), 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]

Zielenkiewicz, Zielenkiewicz, et al., 1984
Zielenkiewicz, A.; Zielenkiewicz, W.; Malanowski, S., Thermodynamic Excess Functions of Dilute Aqueous Solutions of Alkylated Pyrimidines and Aminopurines and Caffeine, Thermochim. Acta, 1984, 74, 95. [all data]

Beak and White, 1982
Beak, P.; White, J.M., Relative enthalpies of 1,3-dimethyl-2,4-pyrimidinedione, 2,4-dimethoxypyrimidine, and 4-methoxy-1-methyl-2-pyrimidinone: estimation of the relative stabilities of two protomers of uracil, J. Am. Chem. Soc., 1982, 104, 7073-7077. [all data]

Murata, Sakiyama, et al., 1985
Murata, S.; Sakiyama, M.; Seki, S., Sublimation calorimetric studies using a calvet microcalorimeter, Thermochimica Acta, 1985, 88, 1, 121-126, https://doi.org/10.1016/0040-6031(85)85419-8 . [all data]

Clark, Peschel, et al., 1965
Clark, L.B.; Peschel, G.G.; Tinoco, I., Jr., Vapor spectra and heats of vaporization of some purine and pyrmidine bases, J. Phys. Chem., 1965, 69, 3615. [all data]

Brunetti, Piacente, et al., 2000
Brunetti, Bruno; Piacente, Vincenzo; Portalone, Gustavo, Sublimation Enthalpies of Some Methyl Derivatives of Uracil from Vapor Pressure Measurements, J. Chem. Eng. Data, 2000, 45, 2, 242-246, https://doi.org/10.1021/je9902802 . [all data]

Teplitsky, Yanson, et al., 1980
Teplitsky, A.B.; Yanson, I.K.; Glukhova, O.T.; Zielenkiwicz, A.; Zielenkiewicz, W.; Wierzchowski, K.L., Thermochemistry of aqueous solutions of alkylated nucleic acid bases, Biophysical Chemistry, 1980, 11, 1, 17-21, https://doi.org/10.1016/0301-4622(80)85003-4 . [all data]

Nowak, Szczepaniak, et al., 1978
Nowak, M.J.; Szczepaniak, K.; Barski, A.; Shugar, D.Z., Z. Naturforsch. C, 1978, 33C, 876. [all data]

Clark, Peschel, et al., 1965, 2
Clark, L.B.; Peschel, G.G.; Tinoco, I., Jr., Vapor spectra and heats of vaporization of some purine and pyrimidine bases, Not In System, 1965, 3615-3618. [all data]

Zielenkiewicz, Zielenkiewicz, et al., 1984, 2
Zielenkiewicz, A.; Zielenkiewicz, W.; Malanowski, S., Thermodynamic excess functions of diluted aqueous solutions of alkylated pyrimidines and amino purines, and caffeine, Thermochim. Acta, 1984, 74, 95-111. [all data]

Domalski and Hearing, 1996
Domalski, Eugene S.; Hearing, Elizabeth D., Heat Capacities and Entropies of Organic Compounds in the Condensed Phase. Volume III, J. Phys. Chem. Ref. Data, 1996, 25, 1, 1, https://doi.org/10.1063/1.555985 . [all data]

Sakiyama and Imamura, 1989
Sakiyama, M.; Imamura, A., Thermoanalytical characterization of 1,3-dimethyluracil and malonamide crystals, Thermochim. Acta, 1989, 142(2), 365-370. [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]

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]


Notes

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Mass spectrum (electron ionization), References