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Synthesis, solvatochromism and crystal structure of 5-Methoxy-5,6-diphenyl-4,5-dihydro-2H -1,2,4-triazine-3-thione.

Rezaei B, Fazlollahi M - Chem Cent J (2013)

Bottom Line: It was found that the monomer of the ligand 5-Methoxy-5,6-diphenyl-4,5-dihydro-2H-1,2,4-triazine-3-thione, further extends into 3D networks via hydrogen bonding and pi-pi stacking interactions.While progressing from the non-polar solvent to the polar one, the main intense band at 310 nm, which is due to the π-π* transition, was red shifted by 13 nm.Thus, the title compound showed positive solvatochromic behavior.

View Article: PubMed Central - HTML - PubMed

Affiliation: Department of Chemistry, Lorestan University, Khorramabad, Iran.

ABSTRACT

Background: For the development of properties in molecular crystals, such as electrical conductivities, magnetic properties, or non-linear optical properties, not only the electronic properties of molecules themselves matter, but also the molecular arrangements in the crystals are very important. Therefore, the design of the crystal structures and the control of molecular arrangements have attracted much attention in recent years. Among various ligands, triazine moieties have been especially interesting because of their biological, pharmacological and medicinal properties.

Results: Crystal structure of 5-Methoxy-5,6-diphenyl-4,5-dihydro-2H-1,2,4-triazine-3-thione is Monoclinic, which consists of space group P21/c with a = 9.699(1), b = 8.500(1), c = 18.044(2) Å, β = 101.290(7)° and Z = 4, R1 = 0.0371 and wR2 = 0.1008 with 2456 reflections (I > 2σ(I)). Intermolecular H bonds between NH groups are acting as donors and S atoms as acceptors. There are also shorted face-to-face as well as edge to face π-π stacking interactions between the parallel aromatic rings. The behavior of solvatochromic of the mentioned compound that involved interhydrogen bonding was investigated by studying its electronic absorption spectra in pure organic solvents of different characters.

Conclusions: The crystal structure of C16H15N3OS, shows the expected face-to-face π-π stacking interactions between aromatic rings of the neighbor chains in this compound. The centroid-centroid distance between the aromatic rings is 3.325 Å. It was found that the monomer of the ligand 5-Methoxy-5,6-diphenyl-4,5-dihydro-2H-1,2,4-triazine-3-thione, further extends into 3D networks via hydrogen bonding and pi-pi stacking interactions. The solvatochromic behavior of the title compound was also investigated by studying its spectra in a selection of different organic solvents. While progressing from the non-polar solvent to the polar one, the main intense band at 310 nm, which is due to the π-π* transition, was red shifted by 13 nm. Thus, the title compound showed positive solvatochromic behavior.

No MeSH data available.


Related in: MedlinePlus

The ORTEP diagram triazine-3-thione of 5-Methoxy-5,6-diphenyl-4,5-dihydro-2H-1,2,4- triazine-3-thione.
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Figure 2: The ORTEP diagram triazine-3-thione of 5-Methoxy-5,6-diphenyl-4,5-dihydro-2H-1,2,4- triazine-3-thione.

Mentions: The crystal structure 5-Methoxy-5,6-diphenyl-4,5-dihydro-2H-1,2,4-triazine-3-thione was solved by direct methods (SIR97) [6] and refined by Full-matrix least squares using the program SHELXTL-97 [7]. The H atoms were refined isotropically. The data had been collected by using a STOE IPDSII. The molecular structure of the title compound is presented in Figure 2. The corresponding crystal and structure refinement data are summarized in Table 1 and all atomic coordinates and equivalent isotropic displacement parameters are given in Table 2. The compound crystallizes in the monoclinic space group P21/c with a = 9.699(1), b = 8.500(1), c = 18.044(2) Å, β = 101.290(7)° and Z = 4. The crystal structure was solved to final values R1 = 0.037 (for 2456 observed rfls. {I > 2σ[I]}) and wR2 = 0.102 (all data), see Additional file 1: Original X-ray analysis data by CIF format.


Synthesis, solvatochromism and crystal structure of 5-Methoxy-5,6-diphenyl-4,5-dihydro-2H -1,2,4-triazine-3-thione.

Rezaei B, Fazlollahi M - Chem Cent J (2013)

The ORTEP diagram triazine-3-thione of 5-Methoxy-5,6-diphenyl-4,5-dihydro-2H-1,2,4- triazine-3-thione.
© Copyright Policy - open-access
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC3750551&req=5

Figure 2: The ORTEP diagram triazine-3-thione of 5-Methoxy-5,6-diphenyl-4,5-dihydro-2H-1,2,4- triazine-3-thione.
Mentions: The crystal structure 5-Methoxy-5,6-diphenyl-4,5-dihydro-2H-1,2,4-triazine-3-thione was solved by direct methods (SIR97) [6] and refined by Full-matrix least squares using the program SHELXTL-97 [7]. The H atoms were refined isotropically. The data had been collected by using a STOE IPDSII. The molecular structure of the title compound is presented in Figure 2. The corresponding crystal and structure refinement data are summarized in Table 1 and all atomic coordinates and equivalent isotropic displacement parameters are given in Table 2. The compound crystallizes in the monoclinic space group P21/c with a = 9.699(1), b = 8.500(1), c = 18.044(2) Å, β = 101.290(7)° and Z = 4. The crystal structure was solved to final values R1 = 0.037 (for 2456 observed rfls. {I > 2σ[I]}) and wR2 = 0.102 (all data), see Additional file 1: Original X-ray analysis data by CIF format.

Bottom Line: It was found that the monomer of the ligand 5-Methoxy-5,6-diphenyl-4,5-dihydro-2H-1,2,4-triazine-3-thione, further extends into 3D networks via hydrogen bonding and pi-pi stacking interactions.While progressing from the non-polar solvent to the polar one, the main intense band at 310 nm, which is due to the π-π* transition, was red shifted by 13 nm.Thus, the title compound showed positive solvatochromic behavior.

View Article: PubMed Central - HTML - PubMed

Affiliation: Department of Chemistry, Lorestan University, Khorramabad, Iran.

ABSTRACT

Background: For the development of properties in molecular crystals, such as electrical conductivities, magnetic properties, or non-linear optical properties, not only the electronic properties of molecules themselves matter, but also the molecular arrangements in the crystals are very important. Therefore, the design of the crystal structures and the control of molecular arrangements have attracted much attention in recent years. Among various ligands, triazine moieties have been especially interesting because of their biological, pharmacological and medicinal properties.

Results: Crystal structure of 5-Methoxy-5,6-diphenyl-4,5-dihydro-2H-1,2,4-triazine-3-thione is Monoclinic, which consists of space group P21/c with a = 9.699(1), b = 8.500(1), c = 18.044(2) Å, β = 101.290(7)° and Z = 4, R1 = 0.0371 and wR2 = 0.1008 with 2456 reflections (I > 2σ(I)). Intermolecular H bonds between NH groups are acting as donors and S atoms as acceptors. There are also shorted face-to-face as well as edge to face π-π stacking interactions between the parallel aromatic rings. The behavior of solvatochromic of the mentioned compound that involved interhydrogen bonding was investigated by studying its electronic absorption spectra in pure organic solvents of different characters.

Conclusions: The crystal structure of C16H15N3OS, shows the expected face-to-face π-π stacking interactions between aromatic rings of the neighbor chains in this compound. The centroid-centroid distance between the aromatic rings is 3.325 Å. It was found that the monomer of the ligand 5-Methoxy-5,6-diphenyl-4,5-dihydro-2H-1,2,4-triazine-3-thione, further extends into 3D networks via hydrogen bonding and pi-pi stacking interactions. The solvatochromic behavior of the title compound was also investigated by studying its spectra in a selection of different organic solvents. While progressing from the non-polar solvent to the polar one, the main intense band at 310 nm, which is due to the π-π* transition, was red shifted by 13 nm. Thus, the title compound showed positive solvatochromic behavior.

No MeSH data available.


Related in: MedlinePlus