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Adenine

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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

Quantity Value Units Method Reference Comment
Proton affinity (review)942.8kJ/molN/AHunter and Lias, 1998HL
Quantity Value Units Method Reference Comment
Gas basicity912.5kJ/molN/AHunter and Lias, 1998HL

Electron affinity determinations

EA (eV) Reference Comment
0.0120 ± 0.0050Desfrancois, Abdoul-Carime, et al., 1996 Aflatooni, Gallup, et al., 1998: vertical attachment EA = -0.54 eV; B

Ionization energy determinations

IE (eV) Method Reference Comment
8.3 ± 0.1EIVerkin, Sukodub, et al., 1976LLK
8.9 ± 0.1EILifschitz, Bergmann, et al., 1967RDSH
8.48PELin, Yu, et al., 1980Vertical value; LLK
8.48PEPeng, Padva, et al., 1976Vertical value; LLK
8.44 ± 0.03PEHush and Cheung, 1975Vertical value; LLK

De-protonation reactions

adeninide anion + Hydrogen cation = Adenine

By formula: C5H4N5- + H+ = C5H5N5

Quantity Value Units Method Reference Comment
Deltar1402. ± 9.2kJ/molG+TSSharma and Lee, 2002gas phase; Acidity at N-9(imidazole N); B
Quantity Value Units Method Reference Comment
Deltar1372. ± 8.4kJ/molIMRBSharma and Lee, 2002gas phase; Acidity at N-9(imidazole N); B
Deltar1441. ± 17.kJ/molIMRBSharma and Lee, 2002gas phase; Less acidic N-10 site(aniline); B

References

Go To: Top, Gas phase ion energetics data, 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]


Notes

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