Startseite Experimental and Computational Studies on Aminoguanidine Free Base, Monocation and Dication, Part II: Acid-Base Properties, Gas Phase Protonation Energies and Total Energies of Two Tautomers of the Free Base
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Experimental and Computational Studies on Aminoguanidine Free Base, Monocation and Dication, Part II: Acid-Base Properties, Gas Phase Protonation Energies and Total Energies of Two Tautomers of the Free Base

  • Jere T. Koskinen , Mikko Koskinen , Ilpo Mutikainen , Pirkko Tilus , Berit Mannfors und Hannu Elo
Veröffentlicht/Copyright: 2. Juni 2014
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Zeitschrift für Naturforschung B
Aus der Zeitschrift Zeitschrift für Naturforschung B Band 52 Heft 10

The structures and protonation energies of aminoguanidine and aminoguanidinium ion were obtained from quantum chemical calculations by using the density functional method B3-LYP and the standard basis set 6 -31 G(d ). The energy differences between the various forms of the two possible tautomers, the endiamine and the imidamide form, were investigated. The endiamine was found to be more stable than the most stable form of the imidamide by 5 kcal/mol in the gas phase. The proton affinity of am inoguanidine was found to be 241.4 kcal/mol (B3 -LYP/6 -31 G(d )) in the gas phase. The liquidation pKa2 for amininoguanidine and the guanidinium ion was determined to be 11.5 ± 0.1. The reference values for guanidine free base and the guanidinium ion are 235.7 kcal/mol and 13.6, respectively. The difference in the order of basicity in the gas phase and in aqueous solution between aminoguanidine and guanidine is discussed in terms of symmetry, resonance, delocalisation, rehybridisation of nitrogen atoms, and electrostatic repulsion.

Keywords: Aminoguanidine; Tautomerism; Resonance; Acid -Base Properties
Received: 1997-4-18
Published Online: 2014-6-2
Published in Print: 1997-10-1

© 1946 – 2014: Verlag der Zeitschrift für Naturforschung

Artikel in diesem Heft

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https://doi.org/10.1515/znb-1997-1018
Schlagwörter für diesen Artikel
Aminoguanidine; Tautomerism; Resonance; Acid -Base Properties

Artikel in diesem Heft

  1. Zu den Phasenverhältnissen im System V/Nb/O, III Die Koexistenzbeziehungen der Mischkristallreihe V1−x-NbxO2 zu den binären und ternären Phasen der Subsysteme VO2/NbO2/V2O3 und VO2/NbO2/V2O 5/Nb2O5 / The Phase Relations in the System V/Nb/O , III Coexistance Relations of Mixed Crystals V1−x-NbxO2 to the Binary and Ternary Phases of Subsystems VO2/NbO2/V2O3 und VO2/NbO2/V2O 5/Nb2O5
  2. Darstellung, 11B-, 13C -, 1H-NMR- und Schwingungsspektren von 2,2' -Bipyridylundecahydro-closo-dodecaborat(1-) sowie Kristallstruktur von (Ph4As)[(2,2′-C10H8N2)B12Hn ]·CH3CN / Synthesis, 11B, 13C, 1H NMR and Vibrational Spectra of 2 ,2'-Bipyridyl-undecahydro-closo-dodecaborate(1-) and Crystal Structure of (Ph4As)[(2 ,2'-C10H8N2)B12H11]-CH3CN
  3. Zum System Ca/Mo/O: Phasendiagramm, Synthese und Charakterisierung der ternären Verbindungen / On the System Ca/Mo/O: Phase Diagram, Synthesis and Characterization of Ternary Compounds
  4. Synthese und Kristallstruktur von Tris(diethylamino)benzylphosphonium- bromiden: [(C2H5)2N]3PCH2C6H5+ Br- · CH3CN und [(C2H5)2N]3PCH2C6H5+ Br3- / Synthesis and Crystal Structures of Tris(diethylamino)benzylphosphonium Bromides: [(C2H5)2N]3PCH2C6H5+ Br- · CH3CN und [(C2H5)2N]3PCH2C6H5+ Br3-
  5. Reactivity and NMR Spectroscopic Properties of Tri(tert-butyl)plumbyl-amine
  6. Reaktion von Cacodylsäure (CH3)2AsOOH im System HF / MF5 (M = As, Sb) und Kristallstruktur von Difluordimethylarsonium- hexafluoroantimonat (CH3)2AsF2SbF6 / Reaction of Cacodylic Acid (CH3)2AsOOH in the System HF / MF5 (M = As, Sb), and Crystal Structure of Difluorodimethylarsonium Hexafluoroantimonate
  7. Darstellung von Cyan-iod-dinitrat NCI(ONO2)2 / Formation of Cyanoiodine Dinitrate NCI(ONO2)2
  8. Synthesis, IR and X-Ray Studies of a Dioxouranium(VI) Nitrate Complex with N,N′-Tetraethyl-N″ -trichloracetylphosphortriamide
  9. Metallkomplexe mit biologisch wichtigen Liganden, XCVI [1] Palladium(II)-, Platin(II)-und Rhodium(I)-Komplexe mit (Phenyl)C-H···Metall-Wechselwirkung von Diphenylmethylen- glycinestern und von 2-Phenyloxazolinonen / Metal Complexes of Biologically Important Ligands, XCVI [1] Palladium(II), Platinum(II) and Rhodium(I) Complexes with (Phenyl)-C-H ··· Metal Interaction of Diphenylmethylene Glycine Esters and from 2-Phenyloxazolones
  10. Phosphanhaltige Palladium(II)-, Platin(II)-und Gold(I)-Komplexe mit dem Di-tbutyliminodicarboxylat-Anion N(C O2tBu)2− / Phosphine Palladium(II), Platinum(II) and Gold(I) Complexes of the Di-tbutyliminocarboxylate Anion N(C O2tBu)2−
  11. Kohlenwasserstoffverbrückte Metallkomplexe, XLIII [1] Addition von η6-Anilin-tricarbonylchrom-Komplexen an den Ethenliganden von [(OC)5Re(η2-C2H4)]+ and [(η5-C5H5)Fe(CO)2(η2-C2H4)]+ / Hydrocarbon Bridged Metal Complexes, XLIII [1] Addition of η6- Aniline Tricarbonyl Chromium Complexes to the Ethene Ligand of [(OC)5Re(η2-C2H4)]+ and [(η5-C5H5)Fe(CO)2(η2-C2H4)]+
  12. Zur Kenntnis eines synthetischen Kentrolits/Melanotekits des Indiums: Pb2In2Si2O9 / On an Synthetic Kentrolite/Melanotekite of Indium: Pb2In2Si2O9
  13. Polysulfonylamine, XCVI [1]. Homokonjugate aus Di(organosulfonyl)aminen und ihren konjugierten Anionen: Vier Kristallstrukturen mit asymmetrischen [N -H ··· N ]--Wasserstoffbrücken / Polysulfonylamines, XCVI [1]. Homoconjugates Formed from Di(organosulfonyl)amines and their Conjugate Anions: Four Crystal Structures Featuring A symmetric [ N - H ··· N ]- Hydrogen Bonds
  14. Polysulfonylamine, XCVII [1] Di(organosulfonyl)amine und ihre konjugierten Anionen als simultane Baugruppen in zwei supramolekularen Strukturen / Polysulfonylamines, XCVII [1] Di(organosulfonyl)amines and their Conjugate Anions as Simultaneous Building Blocks in Two Supramolecular Structures
  15. The Estenfication of Gibberellins with Dimethylformamide Dimethyl Acetal (DMFDMA)
  16. Regioselektive Cyclisierung von Thiocarbonsäureamiden mit Bisimidoyl- chloriden -Synthese von Thiazolidinen mit einer Ketenacetal-Substruktur / Regioselective Cyclization of Thiocarboxylic Amides with Bisimidoyl Chlorides - Synthesis of Thiadiazolidines Containing a Ketenacetal Substructure
  17. Synthesis and Crystal Structures of Indole Derivatives and Indolo[2,3-a]carbazoles as Building Blocks to or as Protein Kinase C Inhibitors
  18. Experimental and Computational Studies on Aminoguanidine Free Base, Monocation and Dication, Part II: Acid-Base Properties, Gas Phase Protonation Energies and Total Energies of Two Tautomers of the Free Base
  19. One-Pot Synthesis of Lanthanide and Yttrium Cryptates Containing Pyridine Units
  20. Notizen: Crystal Structure of Bis(triphenylstannyl)sulfite
  21. Notizen: On the Incorporation of Li(I) into the Fluoroapatite Lattice
  22. Kristallstruktur von Acetat-acidium- hexafluoroantimonat CH3C(OH)2SbF6 Crystal Structure of Acetate Acidium Hexafluoroantimonate CH3C(OH)2SbF6
  23. Notizen: Synthese und Kristallstruktur von [(Ph2PC2H4PPh2)N]Br / Synthesis and Crystal Structure of [(Ph2PC2H4PPh2)N]Br
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