4-Bromo-N-(diethylcarbamothioyl)benzamide

Abstract

The synthesis of the title compound, C12H15BrN2OS, involves the reaction of 4-bromo­benzoyl chloride with potassium thio­cyanate in dry acetone, followed by condensation of 4-bromo­benzoyl isothio­cyanate with diethyl­amine. The carbonyl and thio­carbonyl bond lengths indicate that these correspond to double bonds. The short C—N bond lengths reveal the effects of resonance in this part of the mol­ecule. The conformation of the mol­ecule with respect to the thio­carbonyl and carbonyl units is twisted, with torsion angles of −5.7 (3) and 87.2 (2)°. The N atom of the diethyl­amine group is sp 2-hybridized: the sum of the angles around the N atom is 359.97 (14)°. The two diethyl groups are twisted in + and − anti­periplanar conformations with angles of −179.89 and 179.92°. In the crystal structure, the mol­ecules form infinite chains via an inter­molecular N—H⋯O inter­action.

Crystal and molecular structure of bis(4-bromo-N-(diethylcarbamothioyl)benzamido)nickel(II) complex

“…The same behavior is observed for C-N bond lengths. C-N bond lengths for the investigated complex is shorter than the average single C-N bond length of 1.48 Å, being C1-N1 = 1.335(5) Å, C6-N1= 1.325(6) Å, C1-N2 = 1.334(6) Å, thus showing varying degrees of double bond character [13][14][15][16][17][18][19][20][21][22][23][24][25][26][27]33,34].…”

“…Our group has studied the synthesis [13][14][15][16][17][18][19][20], characterization, crystal structure [21][22][23][24][25][26], thermal behavior [26,27] and antimicrobial activity [28,29] of some substitute benzoylthiourea derivatives and their metal complexes. In the present work, we report the crystal structure of bis (4-…”

Synthesis, characterization and crystal structure of cis-bis[4-fluoro-N-(diethylcarbamothioyl)benzamido-κ2O,S]platinum(II)

“…HL was prepared according to previously published method [45][46][47]. A solution of 4-fluoro benzoyl chloride (5.10 -2 mol) in acetone (50 mL) was added dropwise to a suspension of potassium thiocyanate (5.10 -2 mol) in acetone (30 mL).…”

Crystal structure of 3-(4-bromobenzoyl)- 1,1-diphenylthiourea, C20H15BrN2OS

“…For comparative studies in envisioned coordination compounds, we determined the crystal structure of the title compound. Structural analyses for similar compounds applying diethylamine-as well as di-n-propylamine substituents on the C=S-moiety are apparent in the literature [1,2]. In the title crystal structure, the molecule is present in its O-and Sdiketonic tautomeric form.…”

“…Thesecontactsappearbetween oneofthe Hatoms in ortho-position to the Br atom of the 4-bromophenyl moiety and the doublebonded Oatom.The latter contacts connect the dimeric units to tubes along (100) where the C-H×××Ocontacts run as antidromic chains along the outside of these tubes. In termsofgraph-set analysis [3,4], the descriptor for thehydrogen bonds is R 2 2 8 () on the unitary level while the descriptor for the C-H×××Ocontacts isC 1 1 6 () on the same level. p-Stackingi sn ot ap rominent featureo ft he crystal structure with theclosest distance between two aromatic systemsfound at 4.142(2) Å.…”