On the tautomerism and color origin in solid state of Npy-protonated-2-aminopyridine: spectroscopic elucidation

Chapkanov, A. G.

doi:10.1007/s11224-009-9522-0

Cited by 4 publications

(3 citation statements)

References 34 publications

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“…Moreover, a short exocyclic C-N bond is typically for this cation which represents the so-called imino-form (Scheme 1). The electronic consequences of the mono-protonation of 2-Aminopyridine (Chai et al, 2009;Testa & Wild, 1981) and the electronic structure of the resulting apyH + monocation (Chapkanov, 2010) seem to be well understood. This contribution is part of our ongoing general interest in the hydrogen bonding of polyiodide salts (Reiss & Engel, 2002;Reiss & Engel, 2004;Meyer et al, 2010).…”

Section: S1 Commentmentioning

confidence: 99%

2-Aminopyridin-1-ium triiodide

Reiß¹,

Leske²

2013

Acta Cryst E

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The asymmetric unit of the title compound, C5H7N2 +.I3 −, consists of one 2-aminopyridin-1-ium cation (apyH+) and one triiodide anion, both located in general postions. The apyH+ cation is planar within the experimental uncertainties. The short N—C distance [1.328 (5) Å] of the exocyclic NH2 group is typical for the imino-form of protonated 2-aminopyridines. Consequently, the bond lengths within the six-membered ring vary significantly. The geometric parameters of the triiodide anion are in the typical range, with bond lengths of 2.8966 (3) and 2.9389 (3) Å and a bond angle of 176.02 (1)°. In the crystal, N—H ⋯ I hydrogen bonds connect adjacent ions into screwed chains along the b-axis direction. These chains are twisted pairwise into rectangular rods. The pyridinium moieties of neighbouring rods are arranged parallel to each other with a plane-to-plane distance of 3.423 (5) Å.

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Section: S1 Commentmentioning

confidence: 99%

2-Aminopyridin-1-ium triiodide

Reiß¹,

Leske²

2013

Acta Cryst E

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“…[10] In the case of 2-aminopyridine N py protonation causes partial charge redistribution in the pyridine ring but the aromatic character is retained. [11] These experiments provoke the question: what will be the real situation in 3-AP? Here a correlation between the spectroscopic properties and structure after single and double protonation of 3-AP is carried out by means of UV-, 1 H-NMR, and IR-LD spectroscopy, using the following model systems: protonated 3-AP cations.…”

Section: Introductionmentioning

confidence: 99%

Molecular Spectral Analysis and Ab Initio Calculations of bis(3-aminopyridinium) Tetrachlorocuprate (II), 3-Ammoniumpyridinium Tetrachlorocuprate (II), and bis(3-aminopyridinium) Hexachlorodicuprate (II)

Trendafilova

2015

Spectroscopy Letters

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The aromatic character, distortion, and stabilization as a result of single and double protonation of 3-aminopyridine like three different complex salts were studied by infrared-, ultraviolet spectral analysis, proton nuclear magnetic resonance, and quantum chemical ab initio calculations. Linear-dichroic infrared spectroscopy was applied for identification of the infrared bands. The correlation structure-spectroscopic properties of the model systems are determined: bis(3-aminopyridinium) tetrachlorocuprate (II) salt, where the ring nitrogen atom participates in protonation; 3-ammoniumpyridinium tetrachlorocuprate (II) salt, where both nitrogen atoms are protonated; and a complex with copper (II) bis(3-aminopyridinium) hexachlorodicuprate (II), where the metal ion is coordinated through amino group.

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“…Chapkanov [18] studied 2-aminopyridinium tetrachlorocuprate (II) salt both in solution and in the solid-state using IR and UV-Vis spectroscopy 1 H-NMR, TGV, and DSC methods. A change of aromatic character was explained by the N py protonation that leads to weak charge redistribution in the pyridinium ring and thereby changes in geometrical parameters.…”

Section: Introductionmentioning

confidence: 99%