Synthesis and Crystal Structure of 2-[(E)-2-(4-Ethoxyphenyl)ethenyl]-1-methylpyridinium 4-methylbenzenesulfonate monohydrate

Abstract

Non-linear optics (NLO) has been recognized for several decades as being a promising field with important applications in the domain of opto-electronics and photonics. [1][2][3][4][5] From a literature review we know that a generally popular approach towards NLO materials is to synthesize those compounds that have extended conjugated systems with donor and acceptor groups. However, the mentioned approach will not be affected if the compound crystallizes in a centrosymmetric space group, since the second-order NLO effect requires a noncentrosymmetric structure of the bulk materials. Compounds that are likely to exhibit large values of molecular hyperpolarizability (b) have to have polarizable electrons (conjugated p system) spread over a large distance. 6 Among the known organic NLO materials, ionic chromophores generate much interest because of their large b and easy tunability; thus, by changing the counter anion it is possible to crystallize into noncentrosymmetric structures.7 Styryl pyridinium derivatives are considered to be good conjugated p-systems.In continuation of our on-going research on nonlinear optical materials, 8,9 the title compound (I) ( Fig. 1 and Fig. 2) was synthesized and its X-ray structure was determined in order to obtain detailed information about the molecular packing. However, compound (I) crystallizes in the centrosymmetric monoclinic space group P21/c, and doesn't exhibit second-order12 in hot methanol (50 ml) was mixed with 0.20 g (0.72 mmol) of silver(I) 4-methylbenzenesulfonate in hot methanol (60 ml). The mixture turned yellow and cloudy immediately. After stirring for 30 min, the precipitate of silver iodide was filtered, and the filtrate X-ray Structure Analysis Online The structure of the title compound, C16H18ON + ·C7H7SO3 -·H2O, was synthesized and structurally characterized by singlecrystal X-ray diffraction. The crystal belongs to a monoclinic system with the P21/c space group and cell parameters a = 9.7518 (6) . In the molecular structure, the cation is slightly twisted, and exists in an E configuration. The anion is inclined to the cation with dihedral angles between the benzene ring of the anion and pyridinium and benzene rings of the cation being 89.1(3) and 83.8(3)˚, respectively. In the crystal packing, the cations and anions are individually arranged alternatively into chains along the c-axis, with the cation chains being stacked along the b-axis. The cations, anions and water molecules are interconnected into a 3D network by O-H·O hydrogen bonds and weak C-H·O interactions. Measurements; Bruker APEX2 CCD diffractometer Program system: Apex2 10 Structure determination; direct method (SHELXTL) 11 Re nement: full-matrix least-squares CCDC 714619 Synthesis and Crystal Structure of 2-[(E)-2-(4-Ethoxyphenyl

4-Chloroanilinium 4-methylbenzenesulfonate

“…For background literature concerning molecular-ionic compounds, see: Czupinski et al (2002); Katrusiak & Szafranski (2006). For related structures, see: Chanawanno et al (2009); Chantrapromma et al (2010); Collier et al (2006); Fun et al (2010); Kobkeatthawin et al (2009); Li et al (2005)…”

3-Fluoroanilinium 4-methylbenzenesulfonate

“…For molecular salts as solid forms in pharmaceutical formulations, see: Stahl & Wermuth (2002). For related structures, see: Chanawanno et al (2009); Chantrapromma et al (2010); Collier et al (2006); Fun et al (2010); Li et al (2005); Lin (2010); Tabatabaee & Noozari (2011); Wu et al (2009). For standard bond lengths, see: Allen et al (1987).…”

“…In the title compound, the proton of the sulfonic group of sulfonic acid has been transferred to the N atom of the 3-fluoroaniline molecule, leading to the formation of the molecular complex, (I). Crystal structures of some benzenesulfonate derivatives, viz., 2,4,6-triamino-1,3,5-triazin-1-ium 4-methylbenzenesulfonate monohydrate (Li et al, 2005), ephedrine besylate (Collier et al, 2006), 2-ethyl-6-methylanilinium 4-methylbenzenesulfonate (Wu et al, 2009), 2-[(E)-2-(4-ethoxyphenyl)ethenyl]-1methylpyridinium 4-methylbenzenesulfonate monohydrate (Chanawanno et al, 2009), 2-aminopyrimidin-1-ium 4methylbenzenesulfonate (Tabatabaee & Noozari, 2011), 4-(cyanomethyl)anilinium 4-methylbenzenesulfonate monohydrate (Lin, 2010), 1-methyl-2-[(E)-2-(2-thienyl)etheny] quinolinium 4-bromobenzenesulfonate (Fun et al, 2010) and (E)-2-[4-(dimethylamino)styryl]-1-methylpyridinium 4-methylbenzenesulfonate monohydrate have been reported. In view of the importance of benzenesulphonic acid, we report herein the crystal structure of the title compound (I).…”

3-Chloroanilinium 4-methylbenzenesulfonate

“…For background to molecular-ionic compounds, see: Czupinski et al (2002); Katrusiak & Szafranski (2006). For related structures, see: Chanawanno et al (2009); ; Collier et al (2006); Fun et al (2010); Li et al (2005); Lin (2010); Tabatabaee & Noozari (2011); Wu et al (2009). For normal bond lengths in organic compounds, see: Allen et al (1987).…”

“…A variety of pharmaceutical drugs are prepared as salts of benzenesulfonic acid and are known as besylates. Crystal structures of some benzenesulfonate derivatives, viz., 2,4,6-triamino-1,3,5-triazin-1-ium 4methylbenzenesulfonate monohydrate (Li et al, 2005), ephedrine besylate (Collier et al, 2006), 2-ethyl-6-methylanilinium 4-methylbenzenesulfonate (Wu et al, 2009), 2-[(E)-2-(4-ethoxyphenyl)ethenyl]-1-methylpyridinium 4-methylbenzenesulfonate monohydrate (Chanawanno et al, 2009), 2-aminopyrimidin-1-ium 4-methylbenzenesulfonate (Tabatabaee & Noozari, 2011), 4-(cyanomethyl)anilinium 4-methylbenzenesulfonate monohydrate (Lin, 2010) (Fun et al, 2010) and (E)-2-[4-(dimethylamino)styryl]-1-methylpyridinium 4-methylbenzenesulfonate monohydrate (Chantrapromma et al, 2010) have been reported. In view of the importance of benzenesulphonic acid, we report herein the crystal structure of the title compound (I).…”