1,3,5-Tri-p-tolylbiuret

Abstract

MoOCl2(LOMe) as catalyst, where LOMe is CpCo[P(O)(OMe)2]3, reacts with p‐tolyl isocyanate to afford the title compound, C23H23N3O2. The structural features are the intramolecular hydrogen bond forming a six‐membered ring and a nearly planar arrangement of the biuret moiety. Each p‐tolyl phenyl ring is twisted by approximately 60–80° with respect to the others. The bond lengths N1—C22 of 1.357 (3) Å and N2—C23 of 1.333 (3) Å indicate that they are partial double bonds.

3-(2,3,5,6,7,8-Hexahydro-1H-cyclopenta[b]quinolin-9-yl)-1,5-bis(4-methoxyphenyl)biuret

“…The terminal C1-N2 and C21-N4 bonds are shorter (1.340 (3) and 1.343 (3) Å) than the internal C1-N1 and C21-N1 bonds (1.429 (2) and 1.415 (3) Å). O3 is involved in the hydrogen bonding with H2, forming a six-membered ring, which is consistent with solid state structures of other biuret compounds (Harrison, 2007;Roh and Jeong, 2000). However, the biuret moiety of (I) is not completely planar as the dihedral angle for O3-C21-N1-C1 is 8.8 (3)°.…”

“…For related structures, see: Roh & Jeong (2000); Harrison (2007). Table 1 Hydrogen-bond geometry (Å , ).…”

Structural studies of peri-interactions and bond formation between electron-rich atomic centres and N-phenylcarboxamides or nitroalkenyl groups

“…14, 26 and included in rotaxanes, 27 biologically active materials like glimepiride 28 and as features within large ring systems. 29 Although no structures of acyl ureas with an N-aryl group between the two carbonyls are reported, the closely related triphenylbiuret 15 30 and its tri(2tolyl) analogue 31 have their central aryl ring at 70-71 • to the plane of the hydrogen-bonded ring.…”