Adenine

• Formula: C₅H₅N₅
• Molecular weight: 135.1267
• IUPAC Standard InChI: InChI=1S/C5H5N5/c6-4-3-5(9-1-7-3)10-2-8-4/h1-2H,(H3,6,7,8,9,10) Copy

  
• IUPAC Standard InChIKey: GFFGJBXGBJISGV-UHFFFAOYSA-N Copy
• CAS Registry Number: 73-24-5
• Chemical structure:
  This structure is also available as a 2d Mol file
• Other names: 1H-Purin-6-amine; ADE; Adenin; Adeninimine; Leuco-4; Vitamin B4; 1,6-Dihydro-6-iminopurine; 3,6-Dihydro-6-iminopurine; 6-Amino-1H-purine; 6-Amino-3H-purine; 6-Amino-9H-purine; 6-Aminopurine; 1H-Purine-6-amine; Purine, 6-amino-; USAF CB-18; 1H-Purine, 6-amino-; 6-Amino-7H-purine; 9H-Purine, 1,6-dihydro-6-imino-; 9H-Purin-6-yl-amine; 9H-Purine-6-amine; NSC 14666
• 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)
  • Gas Chromatography
  • References
  • Notes
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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 as indicated in comments:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
AC - 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 as indicated in comments:
B - John E. Bartmess
M - Michael M. Meot-Ner (Mautner) and Sharon G. Lias
RCD - 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: C₅H₄N₅^- + H⁺ = C₅H₅N₅

C₅H₆N₅⁺ +  = (C₅H₆N₅⁺ • )

By formula: C₅H₆N₅⁺ + C₅H₅N₅ = (C₅H₆N₅⁺ • C₅H₅N₅)

 +  = ( • )

By formula: Na⁺ + C₅H₅N₅ = (Na⁺ • C₅H₅N₅)

 +  = ( • )

By formula: Ti⁺ + C₅H₅N₅ = (Ti⁺ • C₅H₅N₅)

 +  = ( • )

By formula: V⁺ + C₅H₅N₅ = (V⁺ • C₅H₅N₅)

 +  = ( • )

By formula: Zn⁺ + C₅H₅N₅ = (Zn⁺ • C₅H₅N₅)

 +  = ( • )

By formula: Fe⁺ + C₅H₅N₅ = (Fe⁺ • C₅H₅N₅)

 +  = ( • )

By formula: Cr⁺ + C₅H₅N₅ = (Cr⁺ • C₅H₅N₅)

 +  = ( • )

By formula: Mn⁺ + C₅H₅N₅ = (Mn⁺ • C₅H₅N₅)

 +  = ( • )

By formula: Ni⁺ + C₅H₅N₅ = (Ni⁺ • C₅H₅N₅)

 +  = ( • )

By formula: Co⁺ + C₅H₅N₅ = (Co⁺ • C₅H₅N₅)

 +  = ( • )

By formula: Cu⁺ + C₅H₅N₅ = (Cu⁺ • C₅H₅N₅)

 +  = ( • )

By formula: K⁺ + C₅H₅N₅ = (K⁺ • C₅H₅N₅)

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:
B - John E. Bartmess
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron

Electron affinity determinations

Ionization energy determinations

De-protonation reactions

 +  =

By formula: C₅H₄N₅^- + H⁺ = C₅H₅N₅

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 as indicated in comments:
M - Michael M. Meot-Ner (Mautner) and Sharon G. Lias
RCD - 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

C₅H₆N₅⁺ +  = (C₅H₆N₅⁺ • )

By formula: C₅H₆N₅⁺ + C₅H₅N₅ = (C₅H₆N₅⁺ • C₅H₅N₅)

 +  = ( • )

By formula: Co⁺ + C₅H₅N₅ = (Co⁺ • C₅H₅N₅)

 +  = ( • )

By formula: Cr⁺ + C₅H₅N₅ = (Cr⁺ • C₅H₅N₅)

 +  = ( • )

By formula: Cu⁺ + C₅H₅N₅ = (Cu⁺ • C₅H₅N₅)

 +  = ( • )

By formula: Fe⁺ + C₅H₅N₅ = (Fe⁺ • C₅H₅N₅)

 +  = ( • )

By formula: K⁺ + C₅H₅N₅ = (K⁺ • C₅H₅N₅)

 +  = ( • )

By formula: Mn⁺ + C₅H₅N₅ = (Mn⁺ • C₅H₅N₅)

 +  = ( • )

By formula: Na⁺ + C₅H₅N₅ = (Na⁺ • C₅H₅N₅)

 +  = ( • )

By formula: Ni⁺ + C₅H₅N₅ = (Ni⁺ • C₅H₅N₅)

 +  = ( • )

By formula: Ti⁺ + C₅H₅N₅ = (Ti⁺ • C₅H₅N₅)

 +  = ( • )

By formula: V⁺ + C₅H₅N₅ = (V⁺ • C₅H₅N₅)

 +  = ( • )

By formula: Zn⁺ + C₅H₅N₅ = (Zn⁺ • C₅H₅N₅)

IR Spectrum

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Data compiled by: Coblentz Society, Inc.

• SOLID (0.9 mg / 650 mg KBr DISC); PERKIN-ELMER 21 (GRATING); (ADJUSTED addcm-110-5-2); 2 cm^-1 resolution
• SOLID (1.4 mg / 360 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

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Additional Data

Gas Chromatography

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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

Normal alkane RI, non-polar column, custom temperature program

View large format table.

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), Gas Chromatography, NIST Free Links, Notes

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

Kirklin and Domalski, 1983
Kirklin, D.R.; Domalski, E.S., Enthalpy of combustion of adenine, J. Chem. Thermodyn., 1983, 15, 941-947. [all data]

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, 1978
Kilday, M.V., Enthalpies of solution of the nucleic acid bases. 1. Adenine in water, J. Res., 1978, NBS 83, 347-369. [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]

Stephenson and Malanowski, 1987
Stephenson, Richard M.; Malanowski, Stanislaw, Handbook of the Thermodynamics of Organic Compounds, 1987, https://doi.org/10.1007/978-94-009-3173-2 . [all data]

Zielenkiewicz, Zielenkiewicz, et al., 1984
Zielenkiewicz, A.; Zielenkiewicz, W.; Sukhodub, L.F.; Glukhova, O.T.; Tepitsky, A.B.; Wierzchowski, K.L., Thermochemistry of aqueous solutions of alkylated nucleic acid bases. v. Enthalpies of hydration of N-methylated adenines, J. Solution Chem., 1984, 13, 757-765. [all data]

Sharma and Lee, 2002
Sharma, S.; Lee, J.K., Acidity of adenine and adenine derivatives and biological implications. A computational and experimental gas-phase study, J. Org. Chem., 2002, 67, 24, 8360-8365, https://doi.org/10.1021/jo0204303 . [all data]

Meot-Ner (Mautner), 1979
Meot-Ner (Mautner), M., Ion Thermochemistry of Low Volatility Compounds in the Gas Phase. II. Intrinsic Basicities and Hydrogen Bonded Dimers of Nitrogen Heterocyclics and Nucleic Bases, J. Am. Chem. Soc., 1979, 101, 9, 2396, https://doi.org/10.1021/ja00503a027 . [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]

Rodgers and Armentrout, 2002
Rodgers, M.T.; Armentrout, P.B., Influence of d orbital occupation on the binding of metal ions to adenine, J. Am. Chem. Soc., 2002, 124, 11, 2678, https://doi.org/10.1021/ja011278+ . [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., 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]

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]

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]

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]

Lin, Yu, et al., 1980
Lin, J.; Yu, C.; Peng, S.; Akiyama, I.; Li, K.; Lee, L.K.; LeBreton, P.R., Ultraviolet photoelectron studies of the ground-state electronic structure and gas-phase tautomerism of purine and adenine, J. Am. Chem. Soc., 1980, 102, 4627. [all data]

Peng, Padva, et al., 1976
Peng, S.; Padva, A.; LeBreton, P.R., Ultraviolet photoelectron studies of biological purines: The valence electronic structure of adenine, Proc. Nat. Acad. Sci. U.S.A., 1976, 73, 2966. [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]

Pellicer, 2007
Pellicer, L.V., Comparison of Sensory Characteristics, and Instrumental flavor Compounds Analysis of Milk Produced by Three Proction Methods. A Thesis presented to the Faculty of the Graduate School University of Missouri-Columbia, 2007, retrieved from http://edit.missouri,edu/Winter2007/Theses/ValverdePellicerL-053107-T6722/research.pdf. [all data]

Notes

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• Symbols used in this document:
  

  Cp,solid	Constant pressure heat capacity of solid
  EA	Electron affinity
  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
  ΔrG°	Free energy of reaction at standard conditions
  ΔrH°	Enthalpy of reaction at standard conditions
  ΔrS°	Entropy 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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