N-Benzoyl-N'-phenylurea

N-Benzoyl-N′-phenylurea

Names
IUPAC name N-(Phenylcarbamoyl)benzamide
Other names 1-Benzoyl-3-phenylurea
Identifiers
CAS Number	1821-33-6
3D model (JSmol)	Interactive image
ChemSpider	67144
PubChem CID	74566
InChI InChI=1S/C14H12N2O2/c17-13(11-7-3-1-4-8-11)16-14(18)15-12-9-5-2-6-10-12/h1-10H,(H2,15,16,17,18) Key: ZWYSLPOHOBPSLC-UHFFFAOYSA-N
SMILES O=C(NC(Nc1ccccc1)=O)c2ccccc2
Properties
Chemical formula	C14H12N2O2
Molar mass	240.26 g·mol−1
Appearance	White crystals
Density	1.259 g cm−3
Melting point	210 to 213 °C (410 to 415 °F; 483 to 486 K)
Refractive index (nD)	1.644
Structure
Crystal structure	monoclinic
Space group	P21/c, No. 14
Lattice constant	a = 15.5641(8) Å, b = 4.6564(3) Å, c = 21.1029(15) Å α = 90°, β = 128.716°, γ = 90°
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

N-Benzoyl-N′-phenylurea is an organic compound with PhCONHCONHPh formula. It is benzoylurea derivative substituted with phenyl group on the opposite nitrogen atom.

Structure of N-benzoyl-N′-phenylurea was first determined in 2010. Molecules in this compound are approximately flat and exhibit high charge delocalization. Within the molecule an intramolecular N−H⋅⋅⋅O hydrogen bond is present forming pseudoaromatic 6-membered ring. Additionally intermolecular N−H⋅⋅⋅O hydrogen bonds are also present combining two molecules into a centrosymmetric dimer (8-membered ring is formed).

Carbonyl C=O bond distances are equal to ca. 1.23 Å, C−N distances are in range of 1.34 to 1.41 Å.

In 1965 N-benzoyl-N′-phenylurea was synthesized when dry N-chlorobenzamide was reacted with phenylisocyanate or refluxed in dry benzene with anhydrous potassium fluoride. Alternatively N-benzoyl-N′-phenylurea was synthesized in 2010 by hydrolysis of N-benzoyl-N′-phenylthiourea.