Abstract
The title compound, 4-(4-chlorophenyl)-4,5-dihydro-1H-1,2,4-triazole-5-thione (1), was synthesized by a hetero-cyclization reaction of 4-chlorophenyl isothiocyanate and formic hydrazide. Compound 1 was characterized by a single-crystal X-ray structure determination as well as 1H and 13C{1H} NMR, IR, and UV spectroscopy, and microelemental analysis. X-ray crystallography on 1 confirms the molecule exists as the thione tautomer and shows the five-membered ring to be planar and to form a dihedral angle of 82.70(5)° with the appended chlorophenyl ring, indicating an almost orthogonal relationship. In the molecular packing, supramolecular dimers are formed via thioamide-N–H⋯S(thione) hydrogen bonds and these are connected by C=S⋯π(triazolyl) and C-Cl⋯π(triazolyl) interactions, leading to a three-dimensional architecture.
Highlights
Nitrogen–sulfur containing heterocyclic ligands, of which the ttiittllee 11,22,44--ttrriiaazole-5-thione is aann eexxaammppllee, aarreewweelllkknnoowwnnfofrorthtehieripr hpahramrmacaoclolgoigcaiclaplopteontetinatlia[1l,[21],2a]ndanadbialibtyilittoy ctoocrodoinrdatienamteetmalest[a3l]s
TThhee aabbsseennccee off aa resonance due to S-H suggests the presence of the thione tautomer in CDCl33 soolluuttiioonn
All standard chemicals and solvents were sourced from Merck (Darmstadt, Germany) and used withoAutllfsutratnhderarpducrihfiecmatiicoanls
Summary
Nitrogen–sulfur containing heterocyclic ligands, of which the ttiittllee 11,,22,,44--ttrriiaazole-5-thione is aann eexxaammppllee,, aarreewweelllkknnoowwnnfofrorthtehieripr hpahramrmacaoclolgoigcaiclaplopteontetinatlia[1l ,[21],2a]ndanadbialibtyilittoy ctoocrodoinrdatienamteetmalest[a3l]s. CHhaeraecinterthizeatsiyont,haensdisX, s-rpaeyctcrroyssctoapl isctrcuhcaturarectdereitzeartmioin,atainond oXf-trhaey tcirtylestcaolmstprouuctnudr,e1d, eStcehremminea1t,ioanreodf ethsceritbiteled.compound, 1, Scheme 1, are described. RReessuullttss aanndd DDiissccuussssiioonn TThhee ttiittllee ccoommppoouunndd ((11)) wwaass pprreeppaarreedd iinn ggoooodd yyiieelldd ((7733%%)) ffrroomm tthhee hheetteerroo--ccyycclliizzaattiioonn rreeaaccttiioonn ooff. TThhee fifinnaall pprroodduucctt wwaasscchhaarraacctteerriizzeeddbbyyssppeeccttrroossccooppyy((11HH aanndd1133CC{{11HH}} NNMMRR,, IIRR,, aanndd UUVV));; sseeee SSuupppplleemmeennttaarryy Materials for original spectra. The NMR data showed the expected resonances and integration (1H). The most notable feature in the 13C{1H} NMR spectrum is the downfield resonance, at δ 167.9 ppm, ascribed to the quaternary-C1 atom. TThhee aabbsseennccee off aa resonance due to S-H suggests the presence of the thione tautomer in CDCl33 soolluuttiioonn. TThhee mmoolleeccuullaarr ssttrruuccttuurree ooff 11 sshhoowwiinngg aattoomm llaabbeelliinngg aanndd ddiissppllaacceemmeenntt eelllliippssooiiddss aatt tthhee 7700%% pprroobbaabbiilliittyy lleevveell.
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