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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.


Thio­semicarbazones can exist as E and Z isomers and they exhibit thione–thiol tautomerism.
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fig1: Thio­semicarbazones can exist as E and Z isomers and they exhibit thione–thiol tautomerism.

Mentions: Thio­semicarbazones and their metal complexes have been widely explored because of their pharmaceutical properties (Klayman et al., 1983 ▸). These compounds present a wide variety of biological activities, such as anti­tumoral, fungicidal and anti­viral (Tarasconi et al., 2000 ▸), and bactericidal (Abram et al., 1998 ▸). The ability of thio­semicarbazone mol­ecules to chelate with traces of metals in biological systems is believed to be a reason for their activity (Teoh et al., 1999 ▸). The nature of the aldehyde and ketone from which the thio­semicarbazone is obtained and the nature of the substituents attached at the +NH2 N atom influence the biological activity (Beraldo & Gambinob, 2004 ▸). Thio­semicarbazones can exist as E and Z isomers and they exhibit thione–thiol tautomerism, as illus­trated for the title compound in Fig. 1 ▸. Complexation usually takes place via dissociation of the acidic proton, resulting in the formation of a five-membered chelate ring (Pal et al., 2002 ▸). The crystal structure of the title compound was determined in order to investigate the extent of electron delocal­ization, the ligand conformation and to explore its biological implications.


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
Thio­semicarbazones can exist as E and Z isomers and they exhibit thione–thiol tautomerism.
© Copyright Policy - open-access
Related In: Results  -  Collection

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

fig1: Thio­semicarbazones can exist as E and Z isomers and they exhibit thione–thiol tautomerism.
Mentions: Thio­semicarbazones and their metal complexes have been widely explored because of their pharmaceutical properties (Klayman et al., 1983 ▸). These compounds present a wide variety of biological activities, such as anti­tumoral, fungicidal and anti­viral (Tarasconi et al., 2000 ▸), and bactericidal (Abram et al., 1998 ▸). The ability of thio­semicarbazone mol­ecules to chelate with traces of metals in biological systems is believed to be a reason for their activity (Teoh et al., 1999 ▸). The nature of the aldehyde and ketone from which the thio­semicarbazone is obtained and the nature of the substituents attached at the +NH2 N atom influence the biological activity (Beraldo & Gambinob, 2004 ▸). Thio­semicarbazones can exist as E and Z isomers and they exhibit thione–thiol tautomerism, as illus­trated for the title compound in Fig. 1 ▸. Complexation usually takes place via dissociation of the acidic proton, resulting in the formation of a five-membered chelate ring (Pal et al., 2002 ▸). The crystal structure of the title compound was determined in order to investigate the extent of electron delocal­ization, the ligand conformation and to explore its biological implications.

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.