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)
- IUPAC Standard InChIKey: GFFGJBXGBJISGV-UHFFFAOYSA-N
- 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
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Gas phase ion energetics data
Go To: Top, 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
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| Proton affinity (review) | 225.3 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
| Quantity | Value | Units | Method | Reference | Comment |
| Gas basicity | 218.1 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
Electron affinity determinations
| EA (eV) | Reference | Comment |
|---|---|---|
| 0.0120 ± 0.0050 | Desfrancois, 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 ± 0.1 | EI | Verkin, Sukodub, et al., 1976 | LLK |
| 8.9 ± 0.1 | EI | Lifschitz, Bergmann, et al., 1967 | RDSH |
| 8.48 | PE | Lin, Yu, et al., 1980 | Vertical value; LLK |
| 8.48 | PE | Peng, Padva, et al., 1976 | Vertical value; LLK |
| 8.44 ± 0.03 | PE | Hush and Cheung, 1975 | Vertical value; LLK |
De-protonation reactions
+
=
By formula: C5H4N5- + H+ = C5H5N5
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 335.1 ± 2.2 | kcal/mol | G+TS | Sharma and Lee, 2002 | gas phase; Acidity at N-9(imidazole N); B |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrG° | 328.0 ± 2.0 | kcal/mol | IMRB | Sharma and Lee, 2002 | gas phase; Acidity at N-9(imidazole N); B |
| ΔrG° | 344.3 ± 4.0 | kcal/mol | IMRB | Sharma and Lee, 2002 | gas 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
Go To: Top, Gas phase ion energetics data, References
- Symbols used in this document:
EA Electron affinity ΔrG° Free energy of reaction at standard conditions ΔrH° Enthalpy of reaction at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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