Uracil
- Formula: C4H4N2O2
- Molecular weight: 112.0868
- IUPAC Standard InChIKey: ISAKRJDGNUQOIC-UHFFFAOYSA-N
- CAS Registry Number: 66-22-8
- Chemical structure:
This structure is also available as a 2d Mol file - Other names: 2,4(1H,3H)-Pyrimidinedione; Pirod; Pyrod; RU 12709; Ura; 2,4-Dihydroxypyrimidine; 2,4-Dioxopyrimidine; 2,4-Pyrimidinediol; 2,4-Pyrimidinedione; 2,6-Dihydroxypyrimidine; Hybar X; 1H-Pyrimidine-2,4-dione; 2-Hydroxy-4(1H)-pyrimidinone; 2-Hydroxy-4(3H)-pyrimidinone; 2,4-Dioxypyrimidine; 4-Hydroxy-2(1H)-pyrimidinone; NSC 3970
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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, Ion clustering data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, 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 | -72.43 ± 0.54 | kcal/mol | Ccr | Nabavian, Sabbah, et al., 1977 |
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 |
---|---|---|---|---|---|
ΔfH°solid | -101.4 ± 0.60 | kcal/mol | Ccb | Wilson, Watson, et al., 1979 | ALS |
ΔfH°solid | -102.67 ± 0.14 | kcal/mol | Ccr | Nabavian, Sabbah, et al., 1977 | ALS |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°solid | -411.40 ± 0.53 | kcal/mol | Ccb | Wilson, Watson, et al., 1979 | ALS |
ΔcH°solid | -410.167 ± 0.067 | kcal/mol | Ccr | Nabavian, Sabbah, et al., 1977 | ALS |
Constant pressure heat capacity of solid
Cp,solid (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
28.80 | 298. | Kilday, 1978 | DH |
Phase change 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:
AC - William E. Acree, Jr., James S. Chickos
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔsubH° | 31. ± 1. | kcal/mol | TE,GS | Bardi, Bencivenni, et al., 1980 | Based on data from 452. to 587. K.; AC |
ΔsubH° | 30.23 ± 0.53 | kcal/mol | V | Nabavian, Sabbah, et al., 1977 | ALS |
ΔsubH° | 20. | kcal/mol | V | Clark, Peschel, et al., 1965 | ALS |
Enthalpy of sublimation
ΔsubH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
29.95 ± 0.05 | 425. | QR,ME | de Barros, Medina, et al., 2006 | Based on data from 315. to 435. K.; AC |
24.21 | 399. to 411. | ME | Szterner, Kaminski, et al., 2002 | AC |
30.35 ± 0.48 | 439. | TE | Brunetti, Piacente, et al., 2000 | Based on data from 394. to 494. K.; AC |
31.21 ± 0.96 | 519. | ME,TE | Bardi, Bencivenni, et al., 1980 | Based on data from 452. to 587. K.; AC |
28.80 ± 0.31 | 403. | QR | Teplitsky, Yanson, et al., 1980 | Based on data from 378. to 428. K.; AC |
29.09 | 425. | MS | Yanson, Teplitsky, et al., 1979 | AC |
32. ± 2. | 523. | HSA | Nowak, Szczepaniak, et al., 1978 | Based on data from 500. to 545. K.; AC |
30.23 ± 0.53 | 440. | C | Nabavian, Sabbah, et al., 1977, 2 | AC |
28.8 ± 1.2 | 426. | LE | Yanson and Teplitskii, 1975 | Based on data from 393. to 458. K. See also Yanson, Verkin, et al., 1974.; AC |
Reaction 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 by: Robert C. Dunbar
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
By formula: Na+ + C4H4N2O2 = (Na+ • C4H4N2O2)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 32.2 ± 0.8 | kcal/mol | CIDT | Rodgers and Armentrout, 2000 | |
ΔrH° | 33.7 | kcal/mol | CIDC | Cerda and Wesdemiotis, 1996 |
By formula: K+ + C4H4N2O2 = (K+ • C4H4N2O2)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 24.1 | kcal/mol | CIDC | Cerda and Wesdemiotis, 1996 |
Gas phase ion energetics 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 evaluated as indicated in comments:
HL - Edward P. Hunter and Sharon G. Lias
Data compiled as indicated in comments:
MM - Michael M. Meot-Ner (Mautner)
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron
B - John E. Bartmess
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Proton affinity (review) | 208.6 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
Quantity | Value | Units | Method | Reference | Comment |
Gas basicity | 201.2 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
Electron affinity determinations
EA (eV) | Method | Reference | Comment |
---|---|---|---|
0.07502 | N/A | Desfrancois, Abdoul-Carime, et al., 1999 | B |
0.0860 ± 0.0080 | LPES | Schiedt, Weinkauf, et al., 1998 | B |
0.054 ± 0.035 | N/A | Desfrancois, Abdoul-Carime, et al., 1996 | B |
0.0930 ± 0.0070 | LPES | Hendricks, Lyapustina, et al., 1996 | Aflatooni, Gallup, et al., 1998: vertical attachment EA = -0.22 eV; B |
2.49 ± 0.10 | LPES | Li, Bowen, et al., 2007 | valence state of rare tautomer(N3-H to C5) inferred from calculations; B |
Proton affinity at 298K
Proton affinity (kcal/mol) | Reference | Comment |
---|---|---|
205. | Wolken and Turecek, 2000 | PA calculated by B3YLP, MP2, QCSID, QCISD(T)6-31G(d,p) to 6-311+G(3df,2p) methods. The results, and comparison with experimental PA of thymine suggest the cited value, probbaly more accurate than 1975 Wilson and McCoskey bracketing value.; MM |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
9.2 | PE | Yu, O'Donnell, et al., 1981 | LLK |
9.4 ± 0.1 | EI | Verkin, Sukodub, et al., 1976 | LLK |
9.53 ± 0.02 | EI | Zaretskii, Sadovskaya, et al., 1971 | LLK |
9.8 ± 0.1 | EI | Lifschitz, Bergmann, et al., 1967 | RDSH |
9.68 | PE | Palmer, Simpson, et al., 1980 | Vertical value; LLK |
9.60 | PE | Dougherty, Wittel, et al., 1976 | Vertical value; LLK |
9.45 | PE | Lauer, Schafer, et al., 1975 | Vertical value; LLK |
9.50 ± 0.03 | PE | Hush and Cheung, 1975 | Vertical value; LLK |
9.59 | PE | Padva, LeBreton, et al., 1974 | Vertical value; LLK |
Ion clustering 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 by: Robert C. Dunbar
Note: Please consider using the reaction search for this species. This page allows searching of all reactions involving this species. Searches may be limited to ion clustering reactions. A general reaction search form is also available.
Clustering reactions
By formula: K+ + C4H4N2O2 = (K+ • C4H4N2O2)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 24.1 | kcal/mol | CIDC | Cerda and Wesdemiotis, 1996 |
By formula: Na+ + C4H4N2O2 = (Na+ • C4H4N2O2)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 32.2 ± 0.8 | kcal/mol | CIDT | Rodgers and Armentrout, 2000 | |
ΔrH° | 33.7 | kcal/mol | CIDC | Cerda and Wesdemiotis, 1996 |
IR Spectrum
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Data compiled by: Coblentz Society, Inc.
- SOLID (0.7 mg / 650 mg KBr DISC); PERKIN-ELMER 21 (GRATING); (ADJUSTED addcm-115-12-3); 2 cm-1 resolution
- SOLID (1.2 mg / 400 mg KBr DISC) $$ PURITY - ANALYTICAL; PERKIN-ELMER 180 (GRATING); DIGITIZED BY COBLENTZ SOCIETY (BATCH II) FROM HARD COPY; 2 cm-1 resolution
- SOLID (SPLIT MULL); DOW KBr FOREPRISM-GRATING; DIGITIZED BY COBLENTZ SOCIETY (BATCH I) FROM HARD COPY; 2 cm-1 resolution
Mass spectrum (electron ionization)
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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 by: NIST Mass Spectrometry Data Center, William E. Wallace, director
Spectrum
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, 1998. |
NIST MS number | 292112 |
UV/Visible spectrum
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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Spectrum
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Additional Data
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Download spectrum in JCAMP-DX format.
Source | Stimson, 1949 |
---|---|
Owner | INEP CP RAS, NIST OSRD Collection (C) 2007 copyright by the U.S. Secretary of Commerce on behalf of the United States of America. All rights reserved. |
Origin | INSTITUTE OF ENERGY PROBLEMS OF CHEMICAL PHYSICS, RAS |
Source reference | RAS UV No. 10472 |
Instrument | n.i.g. |
Melting point | 338 |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Nabavian, Sabbah, et al., 1977
Nabavian, P.M.; Sabbah, R.; Chastel, R.; Laffitte, M.,
Thermodynamique de composes azotes. II. Etude thermochimique des acides aminobenzoiques, de la pyrimidine, de l'uracile et de la thymine.,
J. Chim. Phys., 1977, 74, 115-126. [all data]
Wilson, Watson, et al., 1979
Wilson, S.R.; Watson, I.D.; Malcolm, G.N.,
Enthalpies of formation of solid cytosine, L-histidine, and uracil,
J. Chem. Thermodyn., 1979, 11, 911-912. [all data]
Kilday, 1978
Kilday, M.V.,
Enthalpies of solution of the nucleic acid bases. 4. Uracil in water,
J. Res., 1978, NBS 83, 547-554. [all data]
Bardi, Bencivenni, et al., 1980
Bardi, G.; Bencivenni, L.; Ferro, D.; Martini, B.; Nunziante Cesaro, S.; Teghil, R.,
Thermodynamic study of the vaporization of uracil,
Thermochimica Acta, 1980, 40, 2, 275-282, https://doi.org/10.1016/0040-6031(80)87229-7
. [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]
de Barros, Medina, et al., 2006
de Barros, A.L.F.; Medina, A.; Zappa, F.; Pereira, J.M.; Bessa, E.; Martins, M.H.P.; Coelho, L.F.S.; Wolff, W.; de Castro Faria, N.V.,
A simple experimental arrangement for measuring the vapour pressures and sublimation enthalpies by the Knudsen effusion method: Application to DNA and RNA bases,
Nuclear Instruments and Methods in Physics Research Section A: Accelerators, Spectrometers, Detectors and Associated Equipment, 2006, 560, 2, 219-223, https://doi.org/10.1016/j.nima.2006.01.026
. [all data]
Szterner, Kaminski, et al., 2002
Szterner, Piotr; Kaminski, Miron; Zielenkiewicz, Anna,
Vapour pressures, molar enthalpies of sublimation and molar enthalpies of solution in water of five halogenated derivatives of uracil,
The Journal of Chemical Thermodynamics, 2002, 34, 7, 1005-1012, https://doi.org/10.1006/jcht.2000.0987
. [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]
Yanson, Teplitsky, et al., 1979
Yanson, I.K.; Teplitsky, A.B.; Sukhodub, L.F.,
Experimental studies of molecular interactions between nitrogen bases of nucleic acids,
Biopolymers, 1979, 18, 5, 1149-1170, https://doi.org/10.1002/bip.1979.360180510
. [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]
Nabavian, Sabbah, et al., 1977, 2
Nabavian, M.; Sabbah, R.; Chastel, R.; Laffitte, M.,
J. Chim. Phys.Phys.-Chim. Biol., 1977, 74, 115. [all data]
Yanson and Teplitskii, 1975
Yanson, I.K.; Teplitskii, A.B.,
Zh. Fiz. Khim., 1975, 49, 736. [all data]
Yanson, Verkin, et al., 1974
Yanson, I.K.; Verkin, B.I.; Shklyarevskii, O.I.; Teplitskii, A.B.,
Stud. Biophys., 1974, 46, 1, 29. [all data]
Rodgers and Armentrout, 2000
Rodgers, M.T.; Armentrout, P.B.,
Noncovalent Interactions of Nucleic Acid Bases (Uracil, Thymine, and Adenine) with Alkali Metal Ions. Threshold Collision-Induced Dissociation and Theoretical Studies,
J. Am. Chem. Soc., 2000, 121, 35, 8548, https://doi.org/10.1021/ja001638d
. [all data]
Cerda and Wesdemiotis, 1996
Cerda, B.A.; Wesdemiotis, C.,
PAs of Peptides,
J. Am. Chem. Soc., 1996, 118, 11884. [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]
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]
Schiedt, Weinkauf, et al., 1998
Schiedt, J.; Weinkauf, R.; Neumark, D.M.; Schlag, E.W.,
Anion spectroscopy of uracil, thymine and the amino-oxo and amino-hydroxy tautomers of cytosine and their water clusters,
Chem. Phys., 1998, 239, 1-3, 511-524, https://doi.org/10.1016/S0301-0104(98)00361-9
. [all data]
Desfrancois, Abdoul-Carime, et al., 1996
Desfrancois, C.; Abdoul-Carime, H.; Schermann, J.P.,
Electron Attachment to Isolated Nucleic Acid Bases,
J. Chem. Phys., 1996, 104, 19, 7792, https://doi.org/10.1063/1.471484
. [all data]
Hendricks, Lyapustina, et al., 1996
Hendricks, J.H.; Lyapustina, S.A.; de Clercq, H.L.; Snodgrass, J.T.; Bowen, K.H.,
Dipole bound, nucleic Acid Base Anions Studied via Negative Ion Photoelectron Spectroscopy,
J. Chem. Phys., 1996, 104, 19, 7788, https://doi.org/10.1063/1.471482
. [all data]
Aflatooni, Gallup, et al., 1998
Aflatooni, K.; Gallup, G.A.; Burrows, P.D.,
Electron Attachment Energies of the DNA Bases,
J. Phys. Chem., 1998, 102, 31, 6205, https://doi.org/10.1021/jp980865n
. [all data]
Li, Bowen, et al., 2007
Li, X.; Bowen, K.H.; Haranczyk, M.; Bachorz, R.A.; Mazurkiewicz, K.; Rak, J.; Gutowski, M.,
Photoelectron spectroscopy of adiabatically bound valence anions of rare tautomers of the nucleic acid bases,
J. Chem. Phys., 2007, 127, 17, 174309, https://doi.org/10.1063/1.2795719
. [all data]
Wolken and Turecek, 2000
Wolken, J.K.; Turecek, F.,
Proton affinity of uracil. A computational study of protonation sites,
J. Am. Soc. Mass Spectrom., 2000, 11, 1065. [all data]
Yu, O'Donnell, et al., 1981
Yu, C.; O'Donnell, T.J.; LeBreton, P.R.,
Ultraviolet photoelectron studies of volatile nucleoside models. Vertical ionization potential measurements of methylated uridine, thymidine, cytidine, and adenosine,
J. Phys. Chem., 1981, 85, 3851. [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]
Zaretskii, Sadovskaya, et al., 1971
Zaretskii, V.I.; Sadovskaya, V.L.; Wulfson, N.S.; Sizoy, V.F.; Merimson, V.G.,
Mass spectrometry of steroid systems-XXI. Appearance and ionization potentials for the stereoisomers of the D-homoestrane series,
Org. Mass Spectrom., 1971, 5, 1179. [all data]
Lifschitz, Bergmann, et al., 1967
Lifschitz, C.; Bergmann, E.D.; Pullman, B.,
The ionization potentials of biological purines and pyrimidines,
Tetrahedron Lett., 1967, 4583. [all data]
Palmer, Simpson, et al., 1980
Palmer, M.H.; Simpson, I.; Platenkamp, R.J.,
The electronic structure of flavin derivatives,
J. Mol. Struct., 1980, 66, 243. [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]
Lauer, Schafer, et al., 1975
Lauer, G.; Schafer, W.; Schweig, A.,
Functional subunits in the nucleic acid bases uracil and thymine,
Tetrahedron Lett., 1975, 45, 3939. [all data]
Hush and Cheung, 1975
Hush, N.S.; Cheung, A.S.,
Ionization potentials and donor properties of nucleic acid bases and related compounds,
Chem. Phys. Lett., 1975, 34, 11. [all data]
Padva, LeBreton, et al., 1974
Padva, A.; LeBreton, P.R.; Dinerstein, R.J.; Ridyard, J.N.A.,
UV photoelectron studies of biological pyrimidines: The electronic structure of uracil,
Biochem. Biophys. Res. Commun., 1974, 60, 1262. [all data]
Stimson, 1949
Stimson, M.M.,
J. Am. Chem. Soc., 1949, 71, 1470. [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, Ion clustering data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, References
- Symbols used in this document:
Cp,solid Constant pressure heat capacity of solid EA Electron affinity 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 ΔrH° Enthalpy of reaction at standard conditions ΔsubH Enthalpy of sublimation ΔsubH° Enthalpy of sublimation at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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