1-{[(Z)-Cyclopentylidene]amino}-3-phenylthiourea

Abstract

The sample of the title compound, C12H15N3S, chosen for study consisted of triclinic crystals twinned by a 180° rotation about the a axis. The five-membered ring adopts a twisted conformation. The dihedral angle between the phenyl ring and the mean plane of the thio­urea unit is 78.22 (8)°. In the crystal, molecules are linked via pairs of N—H⋯S hydrogen bonds forming inversion dimers.

The Behavior of (cyclic‐alkylidene)hydrazinecarbothioamides in Cyclization with Dimethyl acetylenedicarboxylate

“…Recently, we have confirmed the structure of 1‐{[ Z ‐cyclopentylidene]amino}‐3‐phenyl‐thiourea 3a , 2‐cycloheptylidene‐ N ‐phenylhydrazinecarbothioamide 3c , and 1‐{(cyclohexylidene)amino}‐3‐(prop‐2‐en‐1‐yl)thiourea 3f via single X‐ray structural determination. From these findings, it is clear that the structure of 3a–m confirm a linear configuration 3A rather than the others (Scheme ).…”

“…Cyclic‐alkylidene‐ N ‐substituted hydrazinecarbothio‐amides 1a–m were prepared according to the published procedures ; the structures of 3a–m were characterized by IR, 1 H‐NMR, and 13 C‐NMR spectra. It is very difficult to differentiate between the linear structure ( 3A ) and alternative isomers triazolidine thiones ( 3B ) as well as thiadiazolidines ( 3C ) (Scheme ) by simple 1 H‐NMR and 13 C‐NMR spectra.…”

“…Cycloalkylidene‐ N ‐substituted hydrazinecarbonthioamides 3a–m was prepared according to the published procedure .…”

“… Colorless crystals (ethanol) (2.21 g, 95%). 1 H‐NMR (300 MHz, CDCl 3 ) δ H = 1.78–1.83 (m, 2H, CH 2 ), 1.88–1.94 (m, 2H, CH 2 ), 2.28–2.34 (m, 2H, CH 2 ), 2.42–2.48 (m, 2H, CH 2 ), 7.20–7.30 (m, 1H, Ar‐H), 7.36–7.42 (m, 2H, Ar‐H), 7.66–7.73 (m, 2H, Ar‐H), 8.56 (br, s, 1H, NH), 9.34 (br, s, 1H, Ph‐NH); 13 C‐NMR (75 MHz, CDCl 3 ) δ C = 25.0, 28.1, 33.5 (CH 2 ), 124.2, 125.9, 128.75 (Ar‐CH), 138.1 (Ar‐C) 162.8 (C = N), 175.9 (C = S).…”

Crystal structure of 3-(prop-2-en-1-yl)-1-{[(1E)-1,2,3,4-tetrahydronaphthalen-1-ylidene]amino}thiourea

“…For a related structure and background to thiosemicarbazones, see: Mohamed et al (2015). For further synthetic details, see: Mague et al (2014…”