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
- Permanent link for this species. Use this link for bookmarking this species for future reference.
- Information on this page:
- Other data available:
- Data at other public NIST sites:
- Options:
Data at NIST subscription sites:
NIST subscription sites provide data under the NIST Standard Reference Data Program, but require an annual fee to access. The purpose of the fee is to recover costs associated with the development of data collections included in such sites. Your institution may already be a subscriber. Follow the links above to find out more about the data in these sites and their terms of usage.
Phase change 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
AC - William E. Acree, Jr., James S. Chickos
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔsubH° | 110. | kJ/mol | V | Clark, Peschel, et al., 1965 | ALS |
Enthalpy of sublimation
ΔsubH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
109.2 | 460.5 | A | Stephenson and Malanowski, 1987 | Based on data from 448. to 473. K.; AC |
127.2 ± 1.9 | 403. to 439. | ME | Zielenkiewicz, Zielenkiewicz, et al., 1984 | AC |
Reaction thermochemistry data
Go To: Top, Phase change 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, Phase change 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.
Clark, Peschel, et al., 1965
Clark, L.B.; Peschel, G.G.; Tinoco, I., Jr.,
Vapor spectra and heats of vaporization of some purine and pyrmidine bases,
J. Phys. Chem., 1965, 69, 3615. [all data]
Stephenson and Malanowski, 1987
Stephenson, Richard M.; Malanowski, Stanislaw,
Handbook of the Thermodynamics of Organic Compounds, 1987, https://doi.org/10.1007/978-94-009-3173-2
. [all data]
Zielenkiewicz, Zielenkiewicz, et al., 1984
Zielenkiewicz, A.; Zielenkiewicz, W.; Sukhodub, L.F.; Glukhova, O.T.; Tepitsky, A.B.; Wierzchowski, K.L.,
Thermochemistry of aqueous solutions of alkylated nucleic acid bases. v. Enthalpies of hydration of N-methylated adenines,
J. Solution Chem., 1984, 13, 757-765. [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, Phase change data, 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 ΔsubH Enthalpy of sublimation ΔsubH° Enthalpy of sublimation at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
- The National Institute of Standards and Technology (NIST) uses its best efforts to deliver a high quality copy of the Database and to verify that the data contained therein have been selected on the basis of sound scientific judgment. However, NIST makes no warranties to that effect, and NIST shall not be liable for any damage that may result from errors or omissions in the Database.
- Customer support for NIST Standard Reference Data products.