Acta Crystallographica Section E Structure Reports Online (Impact Factor: 0.35). 01/2009; DOI: 10.1107/S1600536809003511/at2717Isup2.hkl
Source: DOAJ


The synthesis of the title compound, C14H19BrN2OS, involves the reaction of 4-bromobenzoyl chloride with potassium thiocyanate in acetone followed by condensation of the resulting 4-bromobenzoyl isothiocyanate with di-n-propylamine. Typical thiourea carbonyl and thiocarbonyl double bonds, as well as shortened C—N bonds, are observed in the title compound. The short C—N bond lengths in the centre of the molecule reveal the effects of resonance in this part of the molecule. The asymmetric unit of the title compound contains two crystallographically independent molecules, A and B. There is very little difference between the bond lengths and angles of these molecules. In molecule B, one di-n-propyl group is twisted in a −antiperiplanar conformation with C—C—C—H = −179.1 (3)° and the other adopts a −synclinal conformation with C—C—C—H = −56.7 (4)°; in molecule A the two di-n-propyl groups are twisted in + and −antiperiplanar conformations, with C—C—C—H = −179.9 (3) and 178.2 (3)°, respectively. In the crystal, the molecules are linked into dimeric pairs via pairs of N—H...S hydrogen bonds.

Full-text preview

Available from:
  • Source
    • "Several crystal structures of 1-acyl-thiourea compounds have been reported, establishing that the molecular structure depends on the degree of substitution at the N (3) atom. A summary of recently published X-ray crystal structures of 3-mono-[52–190] and 3,3-di-substituted thioureas [191] [192] [193] [194] [195] [196] [197] [198] [199] [200] [201] [202] [203] [204] [205] [206] [207] [208] [209] [210] [211] [212] [213] [214] [215] [216] are given in Tables S1 and S2, respectively. Although not exhaustive, the list of molecules showed in these tables serves as an updated review on the available molecular and crystal structures and provides a guide for further analysis of structural aspects. "
    [Show abstract] [Hide abstract]
    ABSTRACT: This review provides an overview of the chemistry, structure and potential applications of 1-(acyl/aroyl)-3-(mono-substituted) and 1-(acyl/aroyl)-3,3-(di-substituted) thioureas, with general formula R1C(O)N(1)HC(S)N(3)R2R3. In recent years, the title compounds have found extensive applications as ligands in coordination chemistry. The effect that nitrogen substituents exert on the intra- and intermolecular hydrogen-bonding interactions is discussed, including their role on the coordination properties displayed by these ligands. Novel applications of transition metal complexes bearing 1-(acyl/aroyl)-3-(mono- and di-substituted) thioureas are introduced. Biological aspects are also highlighted. As recently demonstrated, high-throughput screening assay and structure–activity analyses are feasible for this class of compounds. The chemical versatility of 1-(acyl)-3-(substituted) thiourea molecules and the derived metal complexes, together with the possibility of determining detailed structural properties, join biological applications in a promising interdisciplinary approach. The bibliography includes 382 references with emphasis on the literature appearing after 2007.
    Full-text · Article · May 2014 · ChemInform
  • Source
    [Show abstract] [Hide abstract]
    ABSTRACT: A number of N-(arylcarbamothioyl)cyclohexanecarboxamide derivatives (aryl substituents: phenyl, 2-chlorophenyl, 3-chlorophenyl, 4-chlorophenyl, o-tolyl, p-tolyl, 3-methoxyphenyl, 4-methoxyphenyl and naphthalen-1yl) have been synthesized. The compounds obtained were characterized by elemental analyses, IR spectroscopy and (1)H-NMR spectroscopy. N-(naphthalen-1-ylcarbamothioyl)cyclohexanecarboxamide, H(2)L(9), was also characterized by a single crystal X-ray diffraction study. This compound, C(18)H(20)N(2)OS, crystallizes in the triclinic space group Pī, with Z = 2, and unit cell parameters a = 6.9921(14) A, b = 11.002(2) A, c = 12.381(3) A, alpha = 113.28(3) degrees, beta = 99.38(3) degrees, and gamma = 101.85(3) degrees. The cyclohexane ring adopts a chair conformation. The molecular conformation of the compound is stabilized by an intramolecular (N2-H2***O1) hydrogen bond which forms a pseudo-six-membered ring.
    Preview · Article · Feb 2009 · Molecules