C6H5CONHC6H5

C6H5CONHC6H5, commonly known as benzamide or more specifically N-phenylbenzamide, is an organic compound belonging to the class of amides. It consists of a benzoyl group (C6H5CO-) linked to an aniline group (C6H5NH-), forming a secondary amide structure. This compound is notable for its aromatic nature, derived from two benzene rings connected by a carbonyl (C=O) and nitrogen (NH) functional group.

N-phenylbenzamide is typically prepared through the reaction of benzoyl chloride (C6H5COCl) with aniline (C6H5NH2) in the presence of a base, such as sodium hydroxide or pyridine. The reaction proceeds via nucleophilic acyl substitution, where the aniline attacks the electrophilic carbonyl carbon of benzoyl chloride, displacing chloride as a leaving group. Alternative synthesis routes may involve the condensation of benzoic acid with aniline under dehydrating conditions.

The compound exhibits moderate solubility in organic solvents such as ethanol and acetone but is largely insoluble in water due to its nonpolar aromatic structure. N-phenylbenzamide is often used as a model compound in organic chemistry to study amide reactivity, hydrogen bonding, and spectroscopic properties. Its infrared spectrum typically shows characteristic amide I and amide II bands, useful for structural confirmation.

In terms of physical properties, N-phenylbenzamide is a white to off-white crystalline solid with a melting point around 160–163 °C. It is relatively stable under normal conditions but can undergo hydrolysis in the presence of strong acids or bases, reverting to benzoic acid and aniline. The compound also serves as a precursor in the synthesis of various pharmaceutical intermediates and agrochemicals.

While not widely used in industrial applications, N-phenylbenzamide plays a key role in academic research, particularly in the study of amide chemistry and its implications in biochemical processes. Its structural simplicity makes it a valuable reference compound for understanding the behavior of aromatic amides.