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Jin, Zhi‐Min; Pan, Yuanjiang; Liu, Jiageng; Xü, Dong

doi:10.1023/a:1009587232221

Cited by 22 publications

(16 citation statements)

References 3 publications

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“…1, contains a 2-amino-6-methylpyridinium cation, which is protonated at atom N1, and 2-hydroxybenzoate which is deprotonated at its O2 atom. The geometric parameters are comparable with those reported for similar structures (Jin et al, 2000(Jin et al, , 2001Quah et al, 2010).…”

Section: Structure Descriptionsupporting

confidence: 86%

2-Amino-6-methylpyridinium 2-hydroxybenzoate

et al. 2016

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In the title molecular salt, C 6 H 9 N 2 + ÁC 7 H 5 O 3 À , the cation is protonated at its pyridine N atom and and makes a dihedral angle of 16.26 (9) with the plane of the six-membered ring of the anion. The six-membered ring makes a dihedral angle of 6.09 (3) with the attached carboxylate group. In the anion, an intramolecular O-HÁ Á ÁO hydrogen bond generates an S(6) ring motif and a pair of N-HÁ Á ÁO hydrogen bonds generates an R 2 2 (8) ring motif. In the crystal, the anions and cations are linked via N-HÁ Á ÁO hydrogen bonds to form a tetramer. Structure descriptionPyridine and its derivatives play an important role in heterocyclic chemistry (Pozharski et al., 1997;Katritzky et al., 1996) and they are also known to exhibit non-linear optical (NLO) properties (Tomaru et al., 1991). Herein, we report on the synthesis and the crystal structure of the title molecular salt. The title compound, Fig. 1, contains a 2-amino-6-methylpyridinium cation, which is protonated at atom N1, and 2-hydroxybenzoate which is deprotonated at its O2 atom. The geometric parameters are comparable with those reported for similar structures (Jin et al., 2000(Jin et al., , 2001Quah et al., 2010).The benzene ring (C1-C6) of the anion makes a dihedral angle of 6.09 (3) with the attached carboxylate (C7/O2/O3) group. The benzene and pyridine rings are inclined at an angle of 16.26 (9) . In the anion, an intramolecular O-HÁ Á ÁO hydrogen bond generates an S(6) ring motif (Fig. 1). In the crystal, the anions and cations are connected by N-HÁ Á ÁO hydrogen bonds generating an R 2 2 (8) ring motif (Fig. 2). Four pairs of anions and cations are linked by N-HÁ Á ÁO hydrogen bonds (Table 1) to form a tetramer with an R 4 4 (16) ring motif (Fig. 3). 2-Amino-6-picoline (0.54 g) and 2-hydroxybenzoic acid (0.69 g) in an equimolar ratio were mixed in acetone and the mixture was stirred for 3 h. A single crystal of the title compound suitable for X-ray diffraction was obtained by slow evaporation.

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Section: Structure Descriptionsupporting

confidence: 86%

2-Amino-6-methylpyridinium 2-hydroxybenzoate

et al. 2016

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“…For related structures, see: Navarro Ranninger et al (1985); Luque et al (1997); Jin et al (2000); Schuckmann et al (1978); Kü ppers et al (1985); Jessen (1990); Hemamalini & Fun (2010a,b); Quah et al (2010). For hydrogen-bond motifs, see: Bernstein et al (1995).…”

Section: Related Literaturementioning

confidence: 99%

“…There are numerous examples of 2-amino-substituted pyridine compounds in which the 2-aminopyridines act as ligands (Navarro Ranninger et al, 1985) or as protonated cations (Luque et al, 1997;Jin et al, 2000). Phthalic acid forms hydrogenphthalate salts with various organic and other compounds.…”

Section: S1 Commentmentioning

confidence: 99%

2-Amino-6-methylpyridinium 2-carboxybenzoate

2011

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In the title molecular salt, C6H9N2 +·C8H5O4 −, an intramolecular O—H⋯O hydrogen bond occurs within the anion, thereby generating an S(7) ring, which may correlate with the fact that both the carboxylic acid and carboxylate groups are almost coplanar with their attached rings [dihedral angles = 2.9 (3) and 5.2 (3)°, respectively]. In the crystal, each cation is linked to its adjacent anion by two N—H⋯O hydrogen bonds; the dihedral angle between the pyridine and benzene rings is 2.22 (10)°. The ion pairs are linked by further N—H⋯O interactions.

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“…For related structures, see: Albrecht et al (2003); Feng et al (2007); Inuzuka & Fujimoto (1986, 1990; Ishikawa et al (2002); Jin et al (2000Jin et al ( , 2001Jin et al ( , 2005; Luque et al (1997); Nahringbauer & Kvick (1977); Ren et al (2002); Rivas et al (2003); Salwa et al (2008); Xu et al (2006).…”

Section: Related Literaturementioning

confidence: 99%

“…Among them, the tautomerism phenomenon of 2-aminopyridine derivatives has been proved by x-ray diffraction, such as 2-amino-6-methylpyridinium chloride (Jin et al, 2000) and 2-amino-6-methylpyridinium neoabietate (Jin et al, 2005). All the above studies provide important references to further research into 2-amino pyridines.…”

Section: Commentmentioning

confidence: 99%

Tetrakis(2-amino-6-methylpyridinium) hexachloridobismuthate(III) chloride monohydrate

Yang¹,

Chen²,

Xu³

et al. 2009

Acta Cryst E

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The asymmetric unit of the title compound, (C6H9N2)4[BiCl6]Cl·H2O, contains four protonated 2-amino-6-methylpyridine (HAMP) cations and two-halves of two [BiCl6]3− anions, together with one water molecule and one chloride anion. The BiIII atoms are hexacoordinated by Cl atoms, forming distorted octahedral geometries. In the crystal structure, intramolecular O—H⋯Cl and N—H⋯Cl, and intermolecular O—H⋯Cl and N—H⋯O interactions link the molecules into a three-dimensional network.

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Untitled

Cited by 22 publications

References 3 publications

2-Amino-6-methylpyridinium 2-hydroxybenzoate

2-Amino-6-methylpyridinium 2-hydroxybenzoate

2-Amino-6-methylpyridinium 2-carboxybenzoate

Tetrakis(2-amino-6-methylpyridinium) hexachloridobismuthate(III) chloride monohydrate

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