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, 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° | 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 |
By formula: C5H6N5+ + C5H5N5 = (C5H6N5+ • C5H5N5)
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 30.3 | kcal/mol | PHPMS | Meot-Ner (Mautner), 1979 | gas phase; M |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrS° | 39. | cal/mol*K | PHPMS | Meot-Ner (Mautner), 1979 | gas phase; M |
+
= (
•
)
By formula: Na+ + C5H5N5 = (Na+ • C5H5N5)
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 33.4 ± 1.0 | kcal/mol | CIDT | Rodgers and Armentrout, 2000 | RCD |
| ΔrH° | 41.1 | kcal/mol | CIDC | Cerda and Wesdemiotis, 1996 | RCD |
+
= (
•
)
By formula: Ti+ + C5H5N5 = (Ti+ • C5H5N5)
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | ≤81.1 ± 3.5 | kcal/mol | CIDT | Rodgers and Armentrout, 2002 | RCD |
+
= (
•
)
By formula: V+ + C5H5N5 = (V+ • C5H5N5)
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | ≤63.4 ± 2.5 | kcal/mol | CIDT | Rodgers and Armentrout, 2002 | RCD |
+
= (
•
)
By formula: Zn+ + C5H5N5 = (Zn+ • C5H5N5)
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | ≥57.0 ± 1.3 | kcal/mol | CIDT | Rodgers and Armentrout, 2002 | RCD |
+
= (
•
)
By formula: Fe+ + C5H5N5 = (Fe+ • C5H5N5)
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 62.0 ± 2.1 | kcal/mol | CIDT | Rodgers and Armentrout, 2002 | RCD |
+
= (
•
)
By formula: Cr+ + C5H5N5 = (Cr+ • C5H5N5)
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 55.1 ± 1.8 | kcal/mol | CIDT | Rodgers and Armentrout, 2002 | RCD |
+
= (
•
)
By formula: Mn+ + C5H5N5 = (Mn+ • C5H5N5)
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 51.6 ± 1.8 | kcal/mol | CIDT | Rodgers and Armentrout, 2002 | RCD |
+
= (
•
)
By formula: Ni+ + C5H5N5 = (Ni+ • C5H5N5)
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 71.1 ± 2.3 | kcal/mol | CIDT | Rodgers and Armentrout, 2002 | RCD |
+
= (
•
)
By formula: Co+ + C5H5N5 = (Co+ • C5H5N5)
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 70.0 ± 2.5 | kcal/mol | CIDT | Rodgers and Armentrout, 2002 | RCD |
+
= (
•
)
By formula: Cu+ + C5H5N5 = (Cu+ • C5H5N5)
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 70.3 ± 2.6 | kcal/mol | CIDT | Rodgers and Armentrout, 2002 | RCD |
+
= (
•
)
By formula: K+ + C5H5N5 = (K+ • C5H5N5)
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 25.3 | kcal/mol | CIDC | Cerda and Wesdemiotis, 1996 | RCD |
References
Go To: Top, Reaction thermochemistry data, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
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, Reaction thermochemistry data, References
- Symbols used in this document:
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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