Adenine
- Formula: C5H5N5
- Molecular weight: 135.1267
- 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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Condensed phase thermochemistry data
Go To: Top, Reaction thermochemistry data, 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:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DH - Eugene S. Domalski and Elizabeth D. Hearing
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°solid | 96.9 ± 1.3 | kJ/mol | Ccr | Kirklin and Domalski, 1983 | ALS |
ΔfH°solid | 96.02 ± 0.92 | kJ/mol | Ccb | Stiehler and Huffman, 1935 | Reanalyzed by Cox and Pilcher, 1970, Original value = 91.04 kJ/mol; ALS |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°solid | -2779.0 ± 1.3 | kJ/mol | Ccr | Kirklin and Domalski, 1983 | ALS |
ΔcH°solid | -2778.1 ± 0.88 | kJ/mol | Ccb | Stiehler and Huffman, 1935 | Reanalyzed by Cox and Pilcher, 1970, Original value = -2777.1 ± 0.88 kJ/mol; ALS |
Quantity | Value | Units | Method | Reference | Comment |
S°solid,1 bar | 151.01 | J/mol*K | N/A | Stiehler and Huffman, 1935, 2 | Extrapolation below 90 K, 46.69 J/mol*K.; DH |
Constant pressure heat capacity of solid
Cp,solid (J/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
147.0 | 298. | Kilday, 1978 | DH |
143.13 | 298.1 | Stiehler and Huffman, 1935, 2 | T = 88 to 298 K. Value is unsmoothed experimental datum.; DH |
Reaction thermochemistry data
Go To: Top, Condensed phase thermochemistry data, 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:
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
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 1402. ± 9.2 | kJ/mol | G+TS | Sharma and Lee, 2002 | gas phase; Acidity at N-9(imidazole N); B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 1372. ± 8.4 | kJ/mol | IMRB | Sharma and Lee, 2002 | gas phase; Acidity at N-9(imidazole N); B |
ΔrG° | 1441. ± 17. | kJ/mol | IMRB | Sharma and Lee, 2002 | gas phase; Less acidic N-10 site(aniline); B |
By formula: C5H6N5+ + C5H5N5 = (C5H6N5+ • C5H5N5)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 127. | kJ/mol | PHPMS | Meot-Ner (Mautner), 1979 | gas phase; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 160. | J/mol*K | PHPMS | Meot-Ner (Mautner), 1979 | gas phase; M |
By formula: Na+ + C5H5N5 = (Na+ • C5H5N5)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 140. ± 4.2 | kJ/mol | CIDT | Rodgers and Armentrout, 2000 | RCD |
ΔrH° | 172. | kJ/mol | CIDC | Cerda and Wesdemiotis, 1996 | RCD |
By formula: Ti+ + C5H5N5 = (Ti+ • C5H5N5)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | ≤339. ± 15. | kJ/mol | CIDT | Rodgers and Armentrout, 2002 | RCD |
By formula: V+ + C5H5N5 = (V+ • C5H5N5)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | ≤265. ± 10. | kJ/mol | CIDT | Rodgers and Armentrout, 2002 | RCD |
By formula: Zn+ + C5H5N5 = (Zn+ • C5H5N5)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | ≥238. ± 5.4 | kJ/mol | CIDT | Rodgers and Armentrout, 2002 | RCD |
By formula: Fe+ + C5H5N5 = (Fe+ • C5H5N5)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 259. ± 8.8 | kJ/mol | CIDT | Rodgers and Armentrout, 2002 | RCD |
By formula: Cr+ + C5H5N5 = (Cr+ • C5H5N5)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 231. ± 7.5 | kJ/mol | CIDT | Rodgers and Armentrout, 2002 | RCD |
By formula: Mn+ + C5H5N5 = (Mn+ • C5H5N5)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 216. ± 7.5 | kJ/mol | CIDT | Rodgers and Armentrout, 2002 | RCD |
By formula: Ni+ + C5H5N5 = (Ni+ • C5H5N5)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 297. ± 9.6 | kJ/mol | CIDT | Rodgers and Armentrout, 2002 | RCD |
By formula: Co+ + C5H5N5 = (Co+ • C5H5N5)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 293. ± 10. | kJ/mol | CIDT | Rodgers and Armentrout, 2002 | RCD |
By formula: Cu+ + C5H5N5 = (Cu+ • C5H5N5)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 294. ± 11. | kJ/mol | CIDT | Rodgers and Armentrout, 2002 | RCD |
By formula: K+ + C5H5N5 = (K+ • C5H5N5)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 106. | kJ/mol | CIDC | Cerda and Wesdemiotis, 1996 | RCD |
References
Go To: Top, Condensed phase thermochemistry data, Reaction thermochemistry data, 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]
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]
Notes
Go To: Top, Condensed phase thermochemistry data, Reaction thermochemistry data, References
- Symbols used in this document:
Cp,solid Constant pressure heat capacity of solid 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 - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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