N-Benzoyl-N'-phenylurea

N-Benzoyl-N′-phenylurea
Names
	Preferred 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 Ph CO NH CO NH Ph formula. It is benzoylurea derivative substituted with phenyl group on the opposite nitrogen atom.

Structure and bonding edit

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 edit

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 edit

^ ^a ^b ^c 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.

[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.

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