Related Experiment Video
Updated: May 27, 2026
06:46
Facile Preparation of (2Z,4E)-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
(E)-Ethyl 2-cyano-3-(1H-pyrrol-2-yl)acrylate
Acta Crystallographica. Section E, Structure Reports Online
|November 18, 2011
Summary
This study reveals the near-planar structure of a novel organic compound (C10H10N2O2). Adjacent molecules form hydrogen bonds, creating specific crystal lattice structures.
Area of Science:
- Crystallography
- Organic Chemistry
- Supramolecular Chemistry
Background:
- Understanding the three-dimensional arrangement of atoms in organic molecules is crucial for predicting their properties.
- Intermolecular interactions, such as hydrogen bonding, play a significant role in the self-assembly and crystal packing of compounds.
- The specific compound C10H10N2O2 was synthesized and selected for structural analysis.
Purpose of the Study:
- To determine the precise molecular geometry of the title compound, C10H10N2O2.
- To investigate the intermolecular interactions and crystal packing in the solid state.
- To characterize the hydrogen bonding network and identify any resulting supramolecular motifs.
Main Methods:
- Single-crystal X-ray diffraction was employed to obtain the precise atomic coordinates.
- Crystallographic data analysis was performed to assess planarity and identify bond lengths/angles.
- Analysis of intermolecular contacts was conducted to identify hydrogen bonds and other non-covalent interactions.
Main Results:
- The non-hydrogen atoms of C10H10N2O2 exhibit near-planarity, with a maximum deviation of 0.093(1) Å.
- Adjacent molecules are connected via pairs of intermolecular N-H⋯O hydrogen bonds.
- These hydrogen bonds lead to the formation of inversion dimers, characterized by R2(2)(14) ring motifs.
Conclusions:
- The title compound possesses a nearly planar structure, influencing its solid-state arrangement.
- Intermolecular N-H⋯O hydrogen bonding is the primary driving force for crystal packing.
- The formation of inversion dimers represents a common and stable supramolecular assembly in crystalline organic materials.
Related Concept Videos
01:07Alkylation of β-Ketoester Enolates: Acetoacetic Ester Synthesis
Acetoacetic ester synthesis is a method to obtain ketones from alkyl halides and β-keto esters. The reaction occurs in the presence of an alkoxide base that abstracts the acidic proton of the β-keto esters. The step results in an enolate ion which is doubly stabilized. The enolate then reacts with an alkyl halide via the SN2 process to produce an alkylated ester intermediate with a new C–C bond. The hydrolysis of the intermediate, followed by acidification, results in an alkylated β-keto acid.
01:19α-Hydroxy Ketones via Reductive Coupling of Esters: Acyloin Condensation Overview
The pinacol and McMurry reactions involve the reductive coupling of ketones or aldehydes. Similarly, the bimolecular reductive coupling of two ester molecules in the presence of sodium metal in an aprotic solvent yields an α-hydroxy ketone product. The α-hydroxy ketone is also called acyloin, so the reaction is referred to as ‘acyloin condensation.’
01:14Alkylation of β-Diester Enolates: Malonic Ester Synthesis
Malonic ester synthesis is a method to obtain α substituted carboxylic acids from ꞵ-diesters such as diethyl malonate and alkyl halides.
02:42Acidity 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.
02:28Structure and Nomenclature of Ethers
Structure and Bonding
Ethers are organic compounds with an ether functional group which is characterized by an oxygen atom connected to two — identical or different — alkyl, aryl, or vinyl groups. The C–O–C linkage in dimethyl ether — the simplest ether — has an approximately tetrahedral bond angle of 110.3 degrees. The oxygen atom is sp3- hybridized, with the C–O distance being about 140 pm.
Classification of Ethers
Based on their attached substituent groups, ethers can be classified into two...
Ethers are organic compounds with an ether functional group which is characterized by an oxygen atom connected to two — identical or different — alkyl, aryl, or vinyl groups. The C–O–C linkage in dimethyl ether — the simplest ether — has an approximately tetrahedral bond angle of 110.3 degrees. The oxygen atom is sp3- hybridized, with the C–O distance being about 140 pm.
Classification of Ethers
Based on their attached substituent groups, ethers can be classified into two...
02:38Structure and Nomenclature of Epoxides
Cyclic ethers are heterocyclic compounds with an oxygen atom in the ring along with carbon atoms. They are named depending on the number of carbon atoms present in their ring system. Cyclic ethers with a three-membered ring system are called “oxirane”, four-membered ring systems as “oxetane”, five-membered ring systems as “oxolane”, and six-membered ring systems as “oxane”. The cyclic structure of these rings imposes angle strain, and this strain is more in the ring having a smaller number of...