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
  • Mass spectrum (electron ionization)
  • References
  • Notes
• Other data available:
  • UV/Visible spectrum
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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

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

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Additional Data

References

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), Notes

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

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), References

• 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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