2-Amino-6-methylpyridinium 4-methylbenzenesulfonate

Babu, K. Syed Suresh; Dhavamurthy, M.; NizamMohideen, M.; Peramaiyan, G.; Mohan, R.

doi:10.1107/s1600536814008587

Cited by 6 publications

(3 citation statements)

References 21 publications

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“…In the neutral form of 1 d , the average C−N−C angle is 118°, while the average bond angle in 1 d+2TsOH and 1 d+4MSA is 123° (Figure S7). Large C−N−C angles (>120°) suggest a contribution of both pyridinium cation and pyridinylidene resonance structures [76–78] . These results thus suggest that the pyridinic nitrogen atoms of 1 d are fully protonated.…”

Section: Resultsmentioning

confidence: 84%

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Protonation‐Induced Antiaromaticity in Octaaza[8]circulenes: Cyclooctatetraene Scaffolds Constrained with Four Amidine Moieties

Akahori

Kaga

Kim

et al. 2022

Chemistry An Asian Journal

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The switching of cyclic π-conjugation pathways using external stimuli is an attractive research topic in the field of organic chemistry. Here, we synthesized C 4h -symmetric octaaza[8]circulenes with four peripherally arranged amidine moieties that exhibit enhanced antiaromaticity upon protonation. Titration experiments with methanesulfonic acid revealed the formation of the tetraprotonated forms of the octaaza[8]circulenes in solution. Single-crystal X-ray diffraction analyses and theoretical calculations indicated that the contribution of the 8π antiaromatic character of the octaaza[8]circulenes is enhanced by the delocalization of charge through the protonation of the pyridine rings.

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Section: Resultsmentioning

confidence: 84%

“…We also obtained single crystals of the diprotonated species pyridinylidene resonance structures. [76][77][78] These results thus suggest that the pyridinic nitrogen atoms of 1 d are fully protonated. The mean plane deviations of the circulene core in Antiaromaticity of protonated species.…”

Section: Synthesis Structural Characterization and Electrochemistrymentioning

confidence: 74%

Protonation‐Induced Antiaromaticity in Octaaza[8]circulenes: Cyclooctatetraene Scaffolds Constrained with Four Amidine Moieties

Akahori

Kaga

Kim

et al. 2022

Chemistry An Asian Journal

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“…Simple organic-inorganic salts containing strong intermolecular hydrogen bonds have attracted attention as materials which display ferroelectric-paraelectric phase transitions (Sethuram, et al, 2013a,b;Huq et al, 2013;Shihabuddeen Syed et al, 2013;Showrilu et al, 2013). We have recently reported the crystal structures of 2-amino-6-methylpyridinium 2,2,2-trichloroacetate (Babu et al, 2014a), 2amino-6-methylpyridinium 4-methylbenzenesulfonate (Babu et al, 2014b) and 2-amino-5-nitropyridinium hydrogen oxalate (Rajkumar et al, 2014). In a continuation of our studies of pyridinium salts, we report herein on the crystal structure of the title molecular salt, obtained by the reaction of 2-amino-5nitropyridine with sulfamic acid.…”

Section: Chemical Contextmentioning

confidence: 94%

Crystal structure of 2-amino-5-nitropyridinium sulfamate

Rajkumar

NizamMohideen²,

Xavier

et al. 2015

Acta Cryst E

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The crystal structures and Hirshfeld surface analysis of N′,N′′′-((1E,1′E)-{[methylenebis(oxy)]bis(6-bromo-3,1-phenylene)}bis(methanylylidene))bis(isonicotinohydrazide) dihydrate and N′,N′′′-((1E,1′E)-{[butane-1,4-diylbis(oxy)]bis(2,1-phenylene)}bis(methanylylidene))bis(isonicotinohydrazide) [+ solvent]

Abuthahir¹,

NizamMohideen²,

Viswanathan

et al. 2019

Acta Cryst E

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The title compounds, C27H20Br2N6O4·2H2O, (I), and C30H28N6O4·[+ solvent], (II), both crystallize with one half-molecule in the asymmetric unit. The whole molecule of (I) is generated by twofold rotation symmetry, with the twofold rotation axis bisecting the C atom of the –O—CH2—O– bridge. This results in a folded or U-shaped conformation of the molecule. The whole molecule of (II) is generated by inversion symmetry, with the central CH2—CH2 bond of the –O—(CH2)4—O– bridge being located about a center of inversion. This results in a step-like conformation of the molecule. The central C(=O)N—N=C regions of the isonicotinohydrazide moieties in both compounds are planar and the configuration about the imine C=N bonds is E. In compound (I), the benzene and pyridine rings are inclined to each other by 37.60 (6)°. The two symmetry-related pyridine rings are inclined to each other by 74.24 (6)°, and the two symmetry-related benzene rings by 7.69 (6)°. In compound (II), the benzene and pyridine rings are inclined to each other by 25.56 (11)°. The symmetry-related pyridine rings are parallel, as are the two symmetry-related benzene rings. In the crystal of (I), a pair of water molecules link the organic molecules via Owater—H...O and Owater—H...N hydrogen bonds, forming chains along [001], and enclosing an R 4 2(8) and two R 1 2(5) ring motifs. The chains are linked by N—H...Npyridine hydrogen bonds, forming a supramolecular framework. There are also a number of C—H...O hydrogen bonds, and C—H...π and offset π–π interactions [interplanar distance = 3.294 (1) Å] present reinforcing the framework. In the crystal of (II), molecules are linked by N—H...Npyridine hydrogen bonds, forming a supramolecular framework. Here too there are also a number of C—H...O hydrogen bonds present, and a C—H...π interaction, reinforcing the framework. For compound (II), a region of disordered electron density was corrected for using the SQUEEZE [Spek (2015). Acta Cryst. C71, 9–18] routine in PLATON. Their formula mass and unit-cell characteristics were not taken into account during refinement.

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2-Amino-6-methylpyridinium 4-methylbenzenesulfonate

Cited by 6 publications

References 21 publications

Protonation‐Induced Antiaromaticity in Octaaza[8]circulenes: Cyclooctatetraene Scaffolds Constrained with Four Amidine Moieties

Protonation‐Induced Antiaromaticity in Octaaza[8]circulenes: Cyclooctatetraene Scaffolds Constrained with Four Amidine Moieties

Crystal structure of 2-amino-5-nitropyridinium sulfamate

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