Formamide

Formamide, HCONH₂, is the simplest carboxamide and a colorless liquid. Its polarity makes it useful as a solvent and chemical reagent.

Amide: An organic compound containing a carbonyl group bonded to nitrogen. Formamide is the smallest member of this functional-group family.
Amide resonance: Electron delocalization between an amide nitrogen lone pair and its carbonyl group. It gives formamide's C–N bond partial double-bond character.
Polar aprotic solvent: A polar solvent that lacks hydrogen atoms bonded to oxygen or nitrogen for hydrogen-bond donation. Formamide is a highly polar solvent with distinctive hydrogen-bonding behavior.
Acetamide: The amide derived from acetic acid, with formula CH₃CONH₂. Its extra methyl group makes it the next simple primary amide after formamide.
Formic acid: The simplest carboxylic acid, with formula HCOOH. Replacing its hydroxyl group with amino gives formamide.
Dipole moment: A measure of the separation of positive and negative charge in a system. Formamide's strong molecular polarity underlies its interactions with polar solutes.
Polyacrylonitrile: A synthetic polymer made from acrylonitrile units and used in fibers and precursor materials. Formamide can dissolve this polymer in some processing conditions.
Dimethylformamide: A polar aprotic solvent with formula HCON(CH₃)₂. Methyl substitution removes N–H bonds and changes formamide's hydrogen-bond donation.
Carbonyl group: A functional group consisting of a carbon atom double-bonded to oxygen. Its carbonyl carbon is bonded directly to nitrogen in formamide.
Dielectric constant: A measure of how a material reduces the electric field between charges. Formamide's high dielectric response helps it dissolve ionic substances.

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Methyl formateRelated: Methyl formate can react with ammonia to produce formamide.