N-Benzoyl-N′-phenylthiourea

Abstract

Key indicatorsSingle-crystal X-ray study T = 293 K Mean '(C±C) = 0.003 A Ê R factor = 0.045 wR factor = 0.125 Data-to-parameter ratio = 17.9For details of how these key indicators were automatically derived from the article, see

N′-Benzoyl-N-p-bromophenylthiourea

“…Benzoylthiourea derivatives adopt a cis±trans conformation with respect to the position of the substituent and benzoyl groups relative to the S atom across the CÐN bonds (Shanmuga Sundara Raj et al, 1999;Usman et al, 2002;Kaminsky et al, 2002). The structure and bond dimensions of the title compound, (I), are in agreement with those found in arylbenzoylthioureas, including N-phenyl-N H -benzoylthiourea, (II) (Yamin & Yusof, 2003). However, the presence of Br1 at the para position causes the dihedral angle between the bromophenyl plane (C9±C14/Br1) and the central thiourea fragment (S1/C8/N1/N2/C7/O1) to increase from 7.52 (9) in (II) to 20.40 (11) ( Table 1).…”

“…However, the presence of Br1 at the para position causes the dihedral angle between the bromophenyl plane (C9±C14/Br1) and the central thiourea fragment (S1/C8/N1/N2/C7/O1) to increase from 7.52 (9) in (II) to 20.40 (11) ( Table 1). The phenyl (C1±C6) plane and the bromophenyl plane make an angle of 38.61 (11) , compared to 33.3 (1) in (II) (Yamin & Yusof, 2003). The dihedral angle between the phenyl and the central thiourea fragment is 29.93 (11) .…”

Synthesis and Characterization of N-(Arylcarbamothioyl)-cyclohexanecarboxamide Derivatives: The Crystal Structure of N-(Naphthalen-1-ylcarbamothioyl)cyclohexanecarboxamide

“…The bond lengths of the carbonyl (C12-O1 = 1.218(5) Å) and thiocarbonyl (C11-S1 = 1.670(4) Å) groups of the N -(naphthalen-1-ylcarbamothioyl)-cyclohexane carboxamide have typical double-bond character [36,37,38,39,40]. However, the C-N bond lengths for the investigated compound are all shorter than the average single C-N bond length of 1.48 Å, being C12-N1 = 1.388(5) Å, C11-N1= 1.378(5) Å, C11-N2 = 1.340(6) Å, thus showing varying degrees of double bond character [22,39,40,41,42,43,44]. These results are in agreement with the expected delocalization in N -(naphthalen-1-ylcarbamothioyl)cyclohexanecarboxamide and confirmed by C11-N1-C12 = 129.7(4) o and C11-N2-C1 = 122.1(4) o angles showing an sp 2 hybridization on the N1 and N2 atoms.…”

“…These results are in agreement with the expected delocalization in N -(naphthalen-1-ylcarbamothioyl)cyclohexanecarboxamide and confirmed by C11-N1-C12 = 129.7(4) o and C11-N2-C1 = 122.1(4) o angles showing an sp 2 hybridization on the N1 and N2 atoms. As presented in Figure 2, the molecule maintains its cis-trans configuration with respect to the position of the naphthalene and cyclohexane groups relative to the thiocarbonyl sulfur atom across the N1-C11 and N2-C11 bonds, respectively [42,43,44]. …”

New Substituted 1‐Aryl‐4,4,6‐Trimethyl‐3,4‐Dihydropyrimidine‐2‐(1H)Thiones; A Metal‐Free and Solvent‐Free Synthesis, Characterization, and Lymphoid Tyrosine Phosphatase Inhibition Studies

“…The first report includes the unexpected formation of 4,4,6-trimethyl-1-phenyl-3,4-dihydropyrimidine-2 (1H)-thione as a side product during the reaction of cinnamoyl isothiocyanate and aniline to afford the corresponding acyl thiourea derivative in 2005. 10,11 We were the first to demonstrate that dihydropyrimidine-2(1H)thiones are in fact produced by the reaction of aniline, KSCN, and 4-methylpent-3-en-2-one, an aldol condensation product of acetone formed in situ from the acetone used as solvent. Accordingly, the reaction of an acid chloride with KSCN to afford corresponding acyl isothiocayante does not occur; instead, 3,4-dihydropyrimidine-2-thiones are formed by the reaction of acetone dimer with KSCN and aniline without the involvement of the acid chloride used.…”