4-Bromo-N-(di-n-propyl-carbamothioyl)-benzamide.

ABSTRACT: The synthesis of the title compound, C(14)H(19)BrN(2)OS, involves the reaction of 4-bromo-benzoyl chloride with potassium thio-cyanate in acetone followed by condensation of the resulting 4-bromo-benzoyl isothio-cyanate with di-n-propyl-amine. Typical thio-urea carbonyl and thio-carbonyl 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 mol-ecule reveal the effects of resonance in this part of the mol-ecule. The asymmetric unit of the title compound contains two crystallographically independent mol-ecules, A and B. There is very little difference between the bond lengths and angles of these mol-ecules. In mol-ecule B, one di-n-propyl group is twisted in a -anti-periplanar 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 mol-ecule A the two di-n-propyl groups are twisted in + and -anti-periplanar conformations, with C-C-C-H = -179.9?(3) and 178.2?(3)°, respectively. In the crystal, the mol-ecules are linked into dimeric pairs via pairs of N-H?S hydrogen bonds.

SUBMITTER: Binzet G 

PROVIDER: S-EPMC2968555 | biostudies-literature | 2009

REPOSITORIES: biostudies-literature