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;
UNII	LBT1P8UZ0G ;
CompTox Dashboard (EPA)	DTXSID80171247 ;
	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	240.262 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 PhCO NH CO NHPh formula. It is benzoylurea derivative substituted with phenyl group on the opposite nitrogen atom.

Structure and bonding

Structure of N-benzoyl-N′-phenylurea was first determined in 2010.[1] 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.[2] 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.

Centrosymmetric dimer found in crystal structure of N-Benzoyl-N′-phenylurea[1]

Synthesis

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.[3] Alternatively N-benzoyl-N′-phenylurea was synthesized in 2010 by hydrolysis of N-benzoyl-N′-phenylthiourea.[1]

References

Okuniewski, Andrzej; Chojnacki, Jarosław; Becker, Barbara (2010). "N-Benzoyl-N′-phenylurea". Acta Crystallogr. E. 66 (2): o414. doi:10.1107/S1600536810001807. PMC 2979815. PMID 21579832.
Karabıyık, Hasan; Karabıyık, Hande; İskeleli, Nazan (2012). "Hydrogen-bridged chelate ring-assisted π-stacking interactions". Acta Crystallogr. B. 68 (1): 71–79. doi:10.1107/S0108768111052608. PMID 22267560.
Rand, Leon; Dolinski, Richard (1965). "Reactions Catalyzed By Potassium Fluoride. IV. The Reaction of N-Chlorobenzamide with Potassium Fluoride". J. Org. Chem. 30 (1): 48–49. doi:10.1021/jo01012a010.

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[Okuniewski10-1] Okuniewski, Andrzej; Chojnacki, Jarosław; Becker, Barbara (2010). "N-Benzoyl-N′-phenylurea". Acta Crystallogr. E. 66 (2): o414. doi:10.1107/S1600536810001807. PMC 2979815. PMID 21579832.

[2] Karabıyık, Hasan; Karabıyık, Hande; İskeleli, Nazan (2012). "Hydrogen-bridged chelate ring-assisted π-stacking interactions". Acta Crystallogr. B. 68 (1): 71–79. doi:10.1107/S0108768111052608. PMID 22267560.

[3] Rand, Leon; Dolinski, Richard (1965). "Reactions Catalyzed By Potassium Fluoride. IV. The Reaction of N-Chlorobenzamide with Potassium Fluoride". J. Org. Chem. 30 (1): 48–49. doi:10.1021/jo01012a010.