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:
  • Gas phase ion energetics data
  • Ion clustering data
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • Gas Chromatography
  • References
  • Notes
• Other data available:
  • Condensed phase thermochemistry data
  • Phase change data
  • Reaction thermochemistry data
• Data at other public NIST sites:
  • Gas Phase Kinetics Database
• Options:
  • Switch to calorie-based units

Data at NIST subscription sites:

• NIST / TRC Web Thermo Tables, professional edition (thermophysical and thermochemical data)

NIST subscription sites provide data under the NIST Standard Reference Data Program, but require an annual fee to access. The purpose of the fee is to recover costs associated with the development of data collections included in such sites. Your institution may already be a subscriber. Follow the links above to find out more about the data in these sites and their terms of usage.

Gas phase ion energetics data

Go To: Top, Ion clustering data, IR Spectrum, Mass spectrum (electron ionization), Gas Chromatography, References, Notes

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

Go To: Top, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), Gas Chromatography, 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:
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

Go To: Top, Gas phase ion energetics data, Ion clustering data, Mass spectrum (electron ionization), Gas Chromatography, References, Notes

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)

Go To: Top, Gas phase ion energetics data, Ion clustering data, IR Spectrum, Gas Chromatography, 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

Notice: This spectrum may be better viewed with a Javascript and HTML 5 enabled browser.

For Zoom

1.) Enter the desired X axis range (e.g., 100, 200)

2.) Check here for automatic Y scaling

3.) Press here to zoom

Additional Data

Gas Chromatography

Go To: Top, Gas phase ion energetics data, Ion clustering data, IR Spectrum, 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: 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, Gas phase ion energetics data, Ion clustering data, IR Spectrum, Mass spectrum (electron ionization), Gas Chromatography, Notes

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

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]

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, 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]

Cerda and Wesdemiotis, 1996
Cerda, B.A.; Wesdemiotis, C., PAs of Peptides, J. Am. Chem. Soc., 1996, 118, 11884. [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]

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

Go To: Top, Gas phase ion energetics data, Ion clustering data, IR Spectrum, Mass spectrum (electron ionization), Gas Chromatography, References

• Symbols used in this document:
  

  EA	Electron affinity
  ΔrG°	Free energy of reaction at standard conditions
  ΔrH°	Enthalpy of reaction at standard conditions
  ΔrS°	Entropy of reaction at standard conditions

• Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
• The National Institute of Standards and Technology (NIST) uses its best efforts to deliver a high quality copy of the Database and to verify that the data contained therein have been selected on the basis of sound scientific judgment. However, NIST makes no warranties to that effect, and NIST shall not be liable for any damage that may result from errors or omissions in the Database.
• Customer support for NIST Standard Reference Data products.