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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Reaction thermochemistry data

Go To: Top, Gas phase ion energetics data, Ion clustering data, Gas Chromatography, References, Notes

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

+ = Adenine

By formula: C₅H₄N₅^- + H⁺ = C₅H₅N₅

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	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
Δ_rG°	328.0 ± 2.0	kcal/mol	IMRB	Sharma and Lee, 2002	gas phase; Acidity at N-9(imidazole N); B
Δ_rG°	344.3 ± 4.0	kcal/mol	IMRB	Sharma and Lee, 2002	gas phase; Less acidic N-10 site(aniline); B

C₅H₆N₅⁺ + Adenine = (C₅H₆N₅⁺ • Adenine )

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

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	30.3	kcal/mol	PHPMS	Meot-Ner (Mautner), 1979	gas phase; M
Quantity	Value	Units	Method	Reference	Comment
Δ_rS°	39.	cal/mol*K	PHPMS	Meot-Ner (Mautner), 1979	gas phase; M

+ Adenine = ( • Adenine )

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

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	33.4 ± 1.0	kcal/mol	CIDT	Rodgers and Armentrout, 2000	RCD
Δ_rH°	41.1	kcal/mol	CIDC	Cerda and Wesdemiotis, 1996	RCD

+ Adenine = ( • Adenine )

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

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	≤81.1 ± 3.5	kcal/mol	CIDT	Rodgers and Armentrout, 2002	RCD

+ Adenine = ( • Adenine )

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

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	≤63.4 ± 2.5	kcal/mol	CIDT	Rodgers and Armentrout, 2002	RCD

+ Adenine = ( • Adenine )

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

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	≥57.0 ± 1.3	kcal/mol	CIDT	Rodgers and Armentrout, 2002	RCD

+ Adenine = ( • Adenine )

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

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	62.0 ± 2.1	kcal/mol	CIDT	Rodgers and Armentrout, 2002	RCD

+ Adenine = ( • Adenine )

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

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	55.1 ± 1.8	kcal/mol	CIDT	Rodgers and Armentrout, 2002	RCD

+ Adenine = ( • Adenine )

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

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	51.6 ± 1.8	kcal/mol	CIDT	Rodgers and Armentrout, 2002	RCD

+ Adenine = ( • Adenine )

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

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	71.1 ± 2.3	kcal/mol	CIDT	Rodgers and Armentrout, 2002	RCD

+ Adenine = ( • Adenine )

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

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	70.0 ± 2.5	kcal/mol	CIDT	Rodgers and Armentrout, 2002	RCD

+ Adenine = ( • Adenine )

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

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	70.3 ± 2.6	kcal/mol	CIDT	Rodgers and Armentrout, 2002	RCD

+ Adenine = ( • Adenine )

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

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	25.3	kcal/mol	CIDC	Cerda and Wesdemiotis, 1996	RCD

Gas phase ion energetics data

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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

+ = Adenine

By formula: C₅H₄N₅^- + H⁺ = C₅H₅N₅

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	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
Δ_rG°	328.0 ± 2.0	kcal/mol	IMRB	Sharma and Lee, 2002	gas phase; Acidity at N-9(imidazole N); B
Δ_rG°	344.3 ± 4.0	kcal/mol	IMRB	Sharma and Lee, 2002	gas phase; Less acidic N-10 site(aniline); B

Ion clustering data

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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⁺ + Adenine = (C₅H₆N₅⁺ • Adenine )

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

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	30.3	kcal/mol	PHPMS	Meot-Ner (Mautner), 1979	gas phase; M
Quantity	Value	Units	Method	Reference	Comment
Δ_rS°	39.	cal/mol*K	PHPMS	Meot-Ner (Mautner), 1979	gas phase; M

+ Adenine = ( • Adenine )

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

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	70.0 ± 2.5	kcal/mol	CIDT	Rodgers and Armentrout, 2002	RCD

+ Adenine = ( • Adenine )

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

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	55.1 ± 1.8	kcal/mol	CIDT	Rodgers and Armentrout, 2002	RCD

+ Adenine = ( • Adenine )

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

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	70.3 ± 2.6	kcal/mol	CIDT	Rodgers and Armentrout, 2002	RCD

+ Adenine = ( • Adenine )

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

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	62.0 ± 2.1	kcal/mol	CIDT	Rodgers and Armentrout, 2002	RCD

+ Adenine = ( • Adenine )

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

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	25.3	kcal/mol	CIDC	Cerda and Wesdemiotis, 1996	RCD

+ Adenine = ( • Adenine )

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

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	51.6 ± 1.8	kcal/mol	CIDT	Rodgers and Armentrout, 2002	RCD

+ Adenine = ( • Adenine )

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

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	33.4 ± 1.0	kcal/mol	CIDT	Rodgers and Armentrout, 2000	RCD
Δ_rH°	41.1	kcal/mol	CIDC	Cerda and Wesdemiotis, 1996	RCD

+ Adenine = ( • Adenine )

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

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	71.1 ± 2.3	kcal/mol	CIDT	Rodgers and Armentrout, 2002	RCD

+ Adenine = ( • Adenine )

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

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	≤81.1 ± 3.5	kcal/mol	CIDT	Rodgers and Armentrout, 2002	RCD

+ Adenine = ( • Adenine )

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

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	≤63.4 ± 2.5	kcal/mol	CIDT	Rodgers and Armentrout, 2002	RCD

+ Adenine = ( • Adenine )

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

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	≥57.0 ± 1.3	kcal/mol	CIDT	Rodgers and Armentrout, 2002	RCD

Gas Chromatography

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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.

Column type	Active phase	I	Reference	Comment
Capillary	DB-5	1836.	Pellicer, 2007	30. m/0.32 mm/0.25 μm, Helium; Program: not specified

References

Go To: Top, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering data, Gas Chromatography, Notes

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:

EA Electron affinity

Δ_rG° Free energy of reaction at standard conditions

Δ_rH° Enthalpy of reaction at standard conditions

Δ_rS° Entropy of reaction at standard conditions
Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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EA	Electron affinity
Δ_rG°	Free energy of reaction at standard conditions
Δ_rH°	Enthalpy of reaction at standard conditions
Δ_rS°	Entropy of reaction at standard conditions