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Synthesis and crystal structure of (( E )-{2-[( E )-(4-hy ­ droxynaphthalen-1-yl)methyl ­ idene]hydrazin-1-yl}(methyl ­ sulfan ­ yl)methyl ­ idene)azanium hydrogen sulfate monohydrate

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ABSTRACT

In the title hydrated mol­ecular salt, C13H14N3S+·HSO4−·H2O, the protonation of the azomethine N atom in sulfuric acid medium involves the formation of the bis­ulfate anion. The mol­ecular structure of the cation is obtained from the thiol tautomer of thio­semicarbazone wherein the naphthalene moiety and the conjugation of the bonds contribute to the planarity of the mol­ecular skeleton. In the crystal, the cation, anion and water mol­ecule of crystallization are linked by a series of O—H⋯O and N—H⋯O hydrogen bonds, forming a three-dimensional network. Within this network, there are also C—H⋯π inter­actions present involving symmetry-related naphthalene rings.

No MeSH data available.


The synthesis of the title mol­ecular salt.
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fig4: The synthesis of the title mol­ecular salt.

Mentions: The synthesis of the title mol­ecular salt is illustrated in Fig. 4 ▸. An equimolar amount of thio­semicarbazide 10 mmol (0.91 g) and 3-hy­droxy-2-naphthaldehyde 10 mmol (1.72 g) were dissolved in a mixture of methanol and water (30 ml, 50%) and refluxed for 5 h in the presence of a catalytic amount of glacial sulfuric acid. Brown crystals suitable for X-ray diffraction analysis were obtained after slow evaporation of the solution.


Synthesis and crystal structure of (( E )-{2-[( E )-(4-hy ­ droxynaphthalen-1-yl)methyl ­ idene]hydrazin-1-yl}(methyl ­ sulfan ­ yl)methyl ­ idene)azanium hydrogen sulfate monohydrate
The synthesis of the title mol­ecular salt.
© Copyright Policy - open-access
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC5120717&req=5

fig4: The synthesis of the title mol­ecular salt.
Mentions: The synthesis of the title mol­ecular salt is illustrated in Fig. 4 ▸. An equimolar amount of thio­semicarbazide 10 mmol (0.91 g) and 3-hy­droxy-2-naphthaldehyde 10 mmol (1.72 g) were dissolved in a mixture of methanol and water (30 ml, 50%) and refluxed for 5 h in the presence of a catalytic amount of glacial sulfuric acid. Brown crystals suitable for X-ray diffraction analysis were obtained after slow evaporation of the solution.

View Article: PubMed Central - HTML - PubMed

ABSTRACT

In the title hydrated mol­ecular salt, C13H14N3S+·HSO4−·H2O, the protonation of the azomethine N atom in sulfuric acid medium involves the formation of the bis­ulfate anion. The mol­ecular structure of the cation is obtained from the thiol tautomer of thio­semicarbazone wherein the naphthalene moiety and the conjugation of the bonds contribute to the planarity of the mol­ecular skeleton. In the crystal, the cation, anion and water mol­ecule of crystallization are linked by a series of O—H⋯O and N—H⋯O hydrogen bonds, forming a three-dimensional network. Within this network, there are also C—H⋯π inter­actions present involving symmetry-related naphthalene rings.

No MeSH data available.