Related Experiment Video
Updated: May 26, 2026

Microwave-assisted Functionalization of Poly(ethylene glycol) and On-resin Peptides for Use in Chain Polymerizations and Hydrogel Formation
Published on: October 29, 2013
N-(1-Acryloyl-2,2,6,6-tetra-methyl-piperidin-4-yl)acryl-amide
Shailesh K Goswami1, Lyall R Hanton, C John McAdam
1Department of Chemistry, University of Otago, PO Box 56, Dunedin, New Zealand.
Abstract:
The title compound, C(15)H(24)N(2)O(2), crystallizes with two unique mol-ecules, (I) and (II), in the asymmetric unit, differing in the orientation of the acryloyl units with respect to the piperidine rings. The acryl-amide units are essentially planar in both mol-ecules (r.m.s. deviations = 0.042 and 0.024 Å, respectively), as are the C(3)N chains of the acryloyl units. The carbonyl O atoms of the acryloyl systems lie significantly out of these planes, viz. by -0.171 (9) Å for molecule (I) and by 0.33 (1) Å for molecule (II). The acryl-amide and acryloyl planes are inclined at 68.7 (4)° and 59.8 (3)° in the two mol-ecules. The piperidine rings each adopt twist boat conformations. In the crystal, strong N-H⋯O hydrogen bonds link the mol-ecules into zigzag C(4) chains along b. Additional C-H⋯O contacts result in the formation of stacks along a.
More Related Videos
Related Concept Videos
Nomenclature of Carboxylic Acid Derivatives: Amides and Nitriles
The IUPAC and common names of amides are derived from the parent carboxylic acid, by replacing the suffix “oic acid” and “ic acid,” respectively, with “amide.” In the following example, the IUPAC name ethanamide is derived from ethanoic acid, and the common name, acetamide, is obtained from acetic acid.
Amines to Amides: Acylation of Amines
Next, the second equivalent of amine serves as a Brønsted base and deprotonates the quaternary amide...
Structures of Carboxylic Acid Derivatives
Carboxylic acid derivatives contain an acyl group attached to a heteroatom such as chlorine, oxygen, or nitrogen. The carbonyl carbon and oxygen are both sp2-hybridized with an unhybridized p orbital.
The three sp2 orbitals of the carbonyl carbon form three σ bonds, one each with the carbonyl oxygen, the α carbon, and the heteroatom, whereas the other two sp2 orbitals of the carbonyl oxygen are occupied by the lone pairs. Further, the unhybridized p...
Acidity of 1-Alkynes
The acidic strength of hydrocarbons follows the order: Alkynes > Alkenes > Alkanes. The strength of an acid is commonly expressed in units of pKa — the lower the pKa, the stronger the acid. Among the hydrocarbons, terminal alkynes have lower pKa values and are, therefore, more acidic. For example, the pKa values for ethane, ethene, and acetylene are 51, 44, and 25, respectively, as shown here.
Amides to Carboxylic Acids: Hydrolysis
Acid-catalyzed hydrolysis:
Hydrolysis of amides under acidic conditions yields carboxylic acids. Since the reaction occurs slowly, hydrolysis requires the conditions of heat.
The mechanism begins with the protonation of the carbonyl oxygen by the acid catalyst. The protonation makes the amide carbonyl carbon more...
Preparation of Amides
The DCC-promoted synthesis of amides begins with the protonation of DCC by carboxylic acid. The protonation makes it a better acceptor. Next, the addition of carboxylate to the protonated carbodiimide gives a reactive acylating agent.
Subsequently, the amine acts as a nucleophile that attacks the acylating agent to form a tetrahedral intermediate. In the...

