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Compared to amines, amides are very weak bases. While the conjugate acid of an amine has a pK a of about 9.5, the conjugate acid of an amide has a pK a around −0.5. Therefore, compared to amines, amides do not have acid–base properties that are as noticeable in water. This relative lack of basicity is explained by the withdrawing of ...
Amine. In chemistry, amines (/ ə ˈ m iː n, ˈ æ m iː n /, [1] [2] UK also / ˈ eɪ m iː n / [3]) are compounds and functional groups that contain a basic nitrogen atom with a lone pair.Formally, amines are derivatives of ammonia (NH 3 (in which the bond angle between the nitrogen and hydrogen is 107°), wherein one or more hydrogen atoms have been replaced by a substituent such as an ...
Most common imides are prepared by heating dicarboxylic acids or their anhydrides and ammonia or primary amines. The result is a condensation reaction: [5] (RCO) 2 O + R′NH 2 → (RCO) 2 NR′ + H 2 O. These reactions proceed via the intermediacy of amides. The intramolecular reaction of a carboxylic acid with an amide is far faster than the ...
Amidines are much more basic than amides and are among the strongest uncharged/unionized bases. [6] [7] Protonation occurs at the sp 2-hybridized nitrogen. This occurs because the positive charge can be delocalized onto both nitrogen atoms. The resulting cationic species is known as an amidinium ion [8] and possesses identical C-N bond lengths.
Mechanism for acid-catalyzed hydrolysis of an amide. Upon hydrolysis, an amide converts into a carboxylic acid and an amine or ammonia (which in the presence of acid are immediately converted to ammonium salts). One of the two oxygen groups on the carboxylic acid are derived from a water molecule and the amine (or ammonia) gains the hydrogen ion.
Structures of three kinds of amides: an organic amide (carboxamide), a sulfonamide, and a phosphoramide. In chemistry, the term amide (/ ˈ æ m aɪ d / or / ˈ æ m ɪ d / or / ˈ eɪ m aɪ d /) [1] [2] [3] is a compound with the functional group R n E(=O) x NR 2, where x is not zero, E is some element, and each R represents an organic group or hydrogen. [4]
The two major resonance forms of an amide. Another factor that plays a role in determining the reactivity of acyl compounds is resonance. Amides exhibit two main resonance forms. Both are major contributors to the overall structure, so much so that the amide bond between the carbonyl carbon and the amide nitrogen has significant double bond ...
In chemistry, pyramidal inversion (also umbrella inversion) is a fluxional process in compounds with a pyramidal molecule, such as ammonia (NH 3) "turns inside out". [1] [2] It is a rapid oscillation of the atom and substituents, the molecule or ion passing through a planar transition state. [3]