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Adenine

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Condensed phase thermochemistry data

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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
Deltafsolid23.2 ± 0.31kcal/molCcrKirklin and Domalski, 1983ALS
Deltafsolid22.95 ± 0.22kcal/molCcbStiehler and Huffman, 1935Reanalyzed by Cox and Pilcher, 1970, Original value = 21.76 kcal/mol; ALS
Quantity Value Units Method Reference Comment
Deltacsolid-664.20 ± 0.30kcal/molCcrKirklin and Domalski, 1983ALS
Deltacsolid-663.99 ± 0.21kcal/molCcbStiehler and Huffman, 1935Reanalyzed by Cox and Pilcher, 1970, Original value = -663.74 ± 0.21 kcal/mol; ALS
Quantity Value Units Method Reference Comment
solid,1 bar36.092cal/mol*KN/AStiehler and Huffman, 1935, 2Extrapolation below 90 K, 46.69 J/mol*K.; DH

Constant pressure heat capacity of solid

Cp,solid (cal/mol*K) Temperature (K) Reference Comment
35.13298.Kilday, 1978DH
34.209298.1Stiehler and Huffman, 1935, 2T = 88 to 298 K. Value is unsmoothed experimental datum.; DH

Phase change data

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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
Deltasub26.kcal/molVClark, Peschel, et al., 1965ALS

Enthalpy of sublimation

DeltasubH (kcal/mol) Temperature (K) Method Reference Comment
26.10460.5AStephenson and Malanowski, 1987Based on data from 448. - 473. K.; AC
30.40 ± 0.45403. - 439.MEZielenkiewicz, Zielenkiewicz, et al., 1984AC

Reaction thermochemistry data

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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

adeninide anion + Hydrogen cation = Adenine

By formula: C5H4N5- + H+ = C5H5N5

Quantity Value Units Method Reference Comment
Deltar335.1 ± 2.2kcal/molG+TSSharma and Lee, 2002gas phase; Acidity at N-9(imidazole N); B
Quantity Value Units Method Reference Comment
Deltar328.0 ± 2.0kcal/molIMRBSharma and Lee, 2002gas phase; Acidity at N-9(imidazole N); B
Deltar344.3 ± 4.0kcal/molIMRBSharma and Lee, 2002gas phase; Less acidic N-10 site(aniline); B

C5H6N5+ + Adenine = (C5H6N5+ bullet Adenine)

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

Quantity Value Units Method Reference Comment
Deltar30.3kcal/molPHPMSMeot-Ner (Mautner), 1979gas phase; M
Quantity Value Units Method Reference Comment
Deltar39.cal/mol*KPHPMSMeot-Ner (Mautner), 1979gas phase; M

Sodium ion (1+) + Adenine = (Sodium ion (1+) bullet Adenine)

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

Quantity Value Units Method Reference Comment
Deltar33.4 ± 1.0kcal/molCIDTRodgers and Armentrout, 2000RCD
Deltar41.1kcal/molCIDCCerda and Wesdemiotis, 1996RCD

Titanium ion (1+) + Adenine = (Titanium ion (1+) bullet Adenine)

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

Quantity Value Units Method Reference Comment
Deltar<=81.1 ± 3.5kcal/molCIDTRodgers and Armentrout, 2002RCD

Vanadium ion (1+) + Adenine = (Vanadium ion (1+) bullet Adenine)

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

Quantity Value Units Method Reference Comment
Deltar<=63.4 ± 2.5kcal/molCIDTRodgers and Armentrout, 2002RCD

Zinc ion (1+) + Adenine = (Zinc ion (1+) bullet Adenine)

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

Quantity Value Units Method Reference Comment
Deltar>=57.0 ± 1.3kcal/molCIDTRodgers and Armentrout, 2002RCD

Iron ion (1+) + Adenine = (Iron ion (1+) bullet Adenine)

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

Quantity Value Units Method Reference Comment
Deltar62.0 ± 2.1kcal/molCIDTRodgers and Armentrout, 2002RCD

Chromium ion (1+) + Adenine = (Chromium ion (1+) bullet Adenine)

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

Quantity Value Units Method Reference Comment
Deltar55.1 ± 1.8kcal/molCIDTRodgers and Armentrout, 2002RCD

Manganese ion (1+) + Adenine = (Manganese ion (1+) bullet Adenine)

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

Quantity Value Units Method Reference Comment
Deltar51.6 ± 1.8kcal/molCIDTRodgers and Armentrout, 2002RCD

Nickel ion (1+) + Adenine = (Nickel ion (1+) bullet Adenine)

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

Quantity Value Units Method Reference Comment
Deltar71.1 ± 2.3kcal/molCIDTRodgers and Armentrout, 2002RCD

Cobalt ion (1+) + Adenine = (Cobalt ion (1+) bullet Adenine)

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

Quantity Value Units Method Reference Comment
Deltar70.0 ± 2.5kcal/molCIDTRodgers and Armentrout, 2002RCD

Copper ion (1+) + Adenine = (Copper ion (1+) bullet Adenine)

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

Quantity Value Units Method Reference Comment
Deltar70.3 ± 2.6kcal/molCIDTRodgers and Armentrout, 2002RCD

Potassium ion (1+) + Adenine = (Potassium ion (1+) bullet Adenine)

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

Quantity Value Units Method Reference Comment
Deltar25.3kcal/molCIDCCerda and Wesdemiotis, 1996RCD

Gas phase ion energetics data

Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Ion clustering data, IR Spectrum, Mass spectrum (electron ionization), Gas Chromatography, NIST Free Links, 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)225.3kcal/molN/AHunter and Lias, 1998HL
Quantity Value Units Method Reference Comment
Gas basicity218.1kcal/molN/AHunter and Lias, 1998HL

Electron affinity determinations

EA (eV) Reference Comment
0.0120 ± 0.0050Desfrancois, 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 ± 0.1EIVerkin, Sukodub, et al., 1976LLK
8.9 ± 0.1EILifschitz, Bergmann, et al., 1967RDSH
8.48PELin, Yu, et al., 1980Vertical value; LLK
8.48PEPeng, Padva, et al., 1976Vertical value; LLK
8.44 ± 0.03PEHush and Cheung, 1975Vertical value; LLK

De-protonation reactions

adeninide anion + Hydrogen cation = Adenine

By formula: C5H4N5- + H+ = C5H5N5

Quantity Value Units Method Reference Comment
Deltar335.1 ± 2.2kcal/molG+TSSharma and Lee, 2002gas phase; Acidity at N-9(imidazole N); B
Quantity Value Units Method Reference Comment
Deltar328.0 ± 2.0kcal/molIMRBSharma and Lee, 2002gas phase; Acidity at N-9(imidazole N); B
Deltar344.3 ± 4.0kcal/molIMRBSharma and Lee, 2002gas phase; Less acidic N-10 site(aniline); B

Ion clustering data

Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), Gas Chromatography, NIST Free Links, 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:
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+ bullet Adenine)

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

Quantity Value Units Method Reference Comment
Deltar30.3kcal/molPHPMSMeot-Ner (Mautner), 1979gas phase; M
Quantity Value Units Method Reference Comment
Deltar39.cal/mol*KPHPMSMeot-Ner (Mautner), 1979gas phase; M

Cobalt ion (1+) + Adenine = (Cobalt ion (1+) bullet Adenine)

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

Quantity Value Units Method Reference Comment
Deltar70.0 ± 2.5kcal/molCIDTRodgers and Armentrout, 2002RCD

Chromium ion (1+) + Adenine = (Chromium ion (1+) bullet Adenine)

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

Quantity Value Units Method Reference Comment
Deltar55.1 ± 1.8kcal/molCIDTRodgers and Armentrout, 2002RCD

Copper ion (1+) + Adenine = (Copper ion (1+) bullet Adenine)

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

Quantity Value Units Method Reference Comment
Deltar70.3 ± 2.6kcal/molCIDTRodgers and Armentrout, 2002RCD

Iron ion (1+) + Adenine = (Iron ion (1+) bullet Adenine)

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

Quantity Value Units Method Reference Comment
Deltar62.0 ± 2.1kcal/molCIDTRodgers and Armentrout, 2002RCD

Potassium ion (1+) + Adenine = (Potassium ion (1+) bullet Adenine)

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

Quantity Value Units Method Reference Comment
Deltar25.3kcal/molCIDCCerda and Wesdemiotis, 1996RCD

Manganese ion (1+) + Adenine = (Manganese ion (1+) bullet Adenine)

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

Quantity Value Units Method Reference Comment
Deltar51.6 ± 1.8kcal/molCIDTRodgers and Armentrout, 2002RCD

Sodium ion (1+) + Adenine = (Sodium ion (1+) bullet Adenine)

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

Quantity Value Units Method Reference Comment
Deltar33.4 ± 1.0kcal/molCIDTRodgers and Armentrout, 2000RCD
Deltar41.1kcal/molCIDCCerda and Wesdemiotis, 1996RCD

Nickel ion (1+) + Adenine = (Nickel ion (1+) bullet Adenine)

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

Quantity Value Units Method Reference Comment
Deltar71.1 ± 2.3kcal/molCIDTRodgers and Armentrout, 2002RCD

Titanium ion (1+) + Adenine = (Titanium ion (1+) bullet Adenine)

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

Quantity Value Units Method Reference Comment
Deltar<=81.1 ± 3.5kcal/molCIDTRodgers and Armentrout, 2002RCD

Vanadium ion (1+) + Adenine = (Vanadium ion (1+) bullet Adenine)

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

Quantity Value Units Method Reference Comment
Deltar<=63.4 ± 2.5kcal/molCIDTRodgers and Armentrout, 2002RCD

Zinc ion (1+) + Adenine = (Zinc ion (1+) bullet Adenine)

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

Quantity Value Units Method Reference Comment
Deltar>=57.0 ± 1.3kcal/molCIDTRodgers and Armentrout, 2002RCD

IR Spectrum

Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering data, Mass spectrum (electron ionization), Gas Chromatography, NIST Free Links, References, Notes

Data compiled by: Coblentz Society, Inc.


Mass spectrum (electron ionization)

Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering data, IR Spectrum, Gas Chromatography, NIST Free Links, References, Notes

Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director

Spectrum

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Mass spectrum
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Owner NIST Mass Spectrometry Data Center
Collection (C) 2014 copyright by the U.S. Secretary of Commerce
on behalf of the United States of America. All rights reserved.
Origin Japan AIST/NIMC Database- Spectrum MS-NW- 279
NIST MS number 228448

All mass spectra in this site (plus many more) are available from the NIST/EPA/NIH Mass Spectral Library. Please see the following for information about the library and its accompanying search program.


Gas Chromatography

Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering data, IR Spectrum, Mass spectrum (electron ionization), NIST Free Links, References, Notes

Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

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
CapillaryDB-51836.Pellicer, 200730. m/0.32 mm/0.25 «mu»m, Helium; Program: not specified

References

Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering data, IR Spectrum, Mass spectrum (electron ionization), Gas Chromatography, NIST Free Links, 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]

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]

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

Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering data, IR Spectrum, Mass spectrum (electron ionization), Gas Chromatography, NIST Free Links, References