Guanine

• Formula: C₅H₅N₅O
• Molecular weight: 151.1261
• IUPAC Standard InChI: InChI=1S/C5H5N5O/c6-5-9-3-2(4(11)10-5)7-1-8-3/h1H,(H4,6,7,8,9,10,11) Copy

  
• IUPAC Standard InChIKey: UYTPUPDQBNUYGX-UHFFFAOYSA-N Copy
• CAS Registry Number: 73-40-5
• Chemical structure:
  This structure is also available as a 2d Mol file
• Other names: 6H-Purin-6-one, 2-amino-1,7-dihydro-; C.I. Natural White 1; C.I. 75170; Dew Pearl; Guanin; Guanine enol; Hypoxanthine, 2-amino-; Mearlmaid; Natural Pearl Essence; Naturon; Pathocidin; Pearl Essence; Stella Polaris; 2-Amino-6-hydroxypurine; 2-Aminohypoxanthine; 2-Amino-1,7-dihydro-6H-purin-6-one; 6H-Purin-6-one, 2-amino-1,9-dihydro-; Natural White 1
• Permanent link for this species. Use this link for bookmarking this species for future reference.
• Information on this page:
  • Condensed phase thermochemistry data
  • Phase change data
  • Reaction thermochemistry data
  • Gas phase ion energetics data
  • Ion clustering data
  • IR Spectrum
  • References
  • Notes
• Other data available:
  • Mass spectrum (electron ionization)
  • UV/Visible spectrum
• Options:
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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

Constant pressure heat capacity of solid

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 by: William E. Acree, Jr., James S. Chickos

Enthalpy of sublimation

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⁺ + C₅H₅N₅O = (Na⁺ • C₅H₅N₅O)

 +  = ( • )

By formula: K⁺ + C₅H₅N₅O = (K⁺ • C₅H₅N₅O)

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:
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi

Ionization energy determinations

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⁺ + C₅H₅N₅O = (K⁺ • C₅H₅N₅O)

 +  = ( • )

By formula: Na⁺ + C₅H₅N₅O = (Na⁺ • C₅H₅N₅O)

IR Spectrum

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Data compiled by: Coblentz Society, Inc.

• SOLID (1.6 mg / 400 mg KBr DISC) $$ PURITY - ANALYTICAL $$ SEE SPECTRUM NO. 8947 FOR "OIL MULL" RUN; PERKIN-ELMER 180 (GRATING); DIGITIZED BY COBLENTZ SOCIETY (BATCH II) FROM HARD COPY; 2 cm^-1 resolution
• SOLID (SPLIT MULL), FLUOROLUBE FOR 3800-1330 CM^-1, NUJOL FOR 1330-400 CM^-1; BECKMAN IR-9 (GRATING); DIGITIZED BY COBLENTZ SOCIETY (BATCH I) FROM HARD COPY; 2 cm^-1 resolution

References

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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Stiehler and Huffman, 1935
Stiehler, R.D.; Huffman, H.M., Thermal data. IV. The heats of combustion of adenine, hypoxanthine, guanine, xanthine, uric acid, allantoin and alloxan, J. Am. Chem. Soc., 1935, 57, 1734-1740. [all data]

Cox and Pilcher, 1970
Cox, J.D.; Pilcher, G., Thermochemistry of Organic and Organometallic Compounds, Academic Press, New York, 1970, 1-636. [all data]

Stiehler and Huffman, 1935, 2
Stiehler, R.D.; Huffman, H.M., Thermal data. V. The heat capacities, entropies and free energies of adenine, hypoxanthine, guanine, xanthine, uric acid, allantoin and alloxan, J. Am. Chem. Soc., 1935, 57, 1741-1743. [all data]

Kilday, 1981
Kilday, M.V., Enthalpies of solution of the nucleic acid bases. 6. Guanine in aqueous HCl and NaOH, and guanine hydrochlorides in aqueous HCl, J. Res., 1981, NBS 86, 367-381. [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]

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]

Dougherty, Younathan, et al., 1978
Dougherty, D.; Younathan, E.S.; Voll, R.; Abdulnur, S.; McGlynn, S.P., Photoelectron spectroscopy of some biological molecules, J. Electron Spectrosc. Relat. Phenom., 1978, 13, 379. [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]

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]

Notes

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• Symbols used in this document:
  

  Cp,solid	Constant pressure heat capacity of solid
  S°solid,1 bar	Entropy of solid at standard conditions (1 bar)
  ΔcH°solid	Enthalpy of combustion of solid at standard conditions
  ΔfH°solid	Enthalpy of formation of solid at standard conditions
  ΔrH°	Enthalpy of reaction at standard conditions
  ΔsubH	Enthalpy of sublimation

• Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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