Related Experiment Video
Updated: Jun 1, 2026
08:43
Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
Published on: January 19, 2016
Acridinium 2-hy-droxy-benzoate
Hossein Eshtiagh-Hosseini1, Azam Hassanpoor, Masoud Mirzaei
1Department of Chemistry, School of Sciences, Ferdowsi University of Mashhad, Mashhad, Iran.
Summary
This study characterizes the crystal structure of acridinium salicylate, detailing the protonation states and planar arrangements of the acridinium cation and salicylate anion. Intermolecular hydrogen bonds and C-H···π interactions stabilize the crystal lattice.
Area of Science:
- Crystal chemistry
- Supramolecular chemistry
- Organic chemistry
Background:
- Acridinium and salicylate are key organic moieties with diverse applications.
- Understanding their ionic interactions is crucial for materials science.
- Proton transfer and hydrogen bonding influence molecular assembly.
Purpose of the Study:
- To elucidate the crystal structure of the acridinium salicylate salt.
- To analyze the molecular geometry and intermolecular interactions.
- To investigate the role of hydrogen bonding and pi-stacking in crystal stabilization.
Main Methods:
- Single-crystal X-ray diffraction analysis.
- Analysis of bond lengths, bond angles, and dihedral angles.
- Identification and characterization of intermolecular interactions (hydrogen bonds, C-H···π).
Main Results:
- The asymmetric unit contains one acridinium cation and one salicylate anion.
- Both the acridinium cation and salicylate anion moieties are planar.
- A dihedral angle of 71.68° exists between the cation and anion.
- Crystal structure is stabilized by N-H⋯O, O-H⋯O, and C-H⋯O hydrogen bonds, along with C-H⋯π interactions.
Conclusions:
- The study provides a detailed structural description of acridinium salicylate.
- Hydrogen bonding and C-H⋯π interactions are key factors in the crystal packing.
- The findings contribute to the understanding of ionic organic salt structures and their stabilization mechanisms.
Related Concept Videos
01:19Diazonium Group Substitution: –OH and –H
Nitrous acid, a weak acid, is prepared in situ via the reaction of sodium nitrite with a strong acid under cold conditions. This nitrous acid prepared in situ reacts with primary arylamines to form arenediazonium salts. Such reactions are known as diazotization reactions. As shown in Figure 1, the formation of arenediazonium salts begins with the decomposition of nitrous acid in an acidic solution to give nitrosonium ions.
01:29Indirect-Acting Cholinergic Agonists: Chemistry and Structure-Activity Relationship
Indirect-acting cholinergic agonists are agents that interact with the acetylcholinesterase enzyme in the synaptic cleft, preventing the breakdown of acetylcholine into choline and acetate. Consequently, the concentration of acetylcholine in the synaptic cleft increases. These agonists can be classified into reversible and irreversible inhibitors based on their duration of action.
Reversible inhibitors display short to medium durations of action. Short-acting agents include simple alcohols with...
Reversible inhibitors display short to medium durations of action. Short-acting agents include simple alcohols with...
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.
01:18Indirect-Acting Cholinergic Agonists: Mechanism of Action
Indirect-acting cholinergic agonists work by interacting with an enzyme called acetylcholinesterase (AChE) in the synaptic cleft. They can be reversible or irreversible inhibitors and have different effects on the enzyme.
Reversible inhibitors like edrophonium bind to a specific part of the enzyme called the anionic catalytic site. They form noncovalent bonds, which means they are not strongly attached to the enzyme. This creates a temporary and less stable enzyme–inhibitor complex, leading to...
Reversible inhibitors like edrophonium bind to a specific part of the enzyme called the anionic catalytic site. They form noncovalent bonds, which means they are not strongly attached to the enzyme. This creates a temporary and less stable enzyme–inhibitor complex, leading to...
01:11Nucleophilic Aromatic Substitution: Elimination–Addition
Simple aryl halides do not react with nucleophiles. However, nucleophilic aromatic substitutions can be forced under certain conditions, such as high temperatures or strong bases. The mechanism of substitution under such conditions involves the highly unstable and reactive benzyne intermediate. Benzyne contains equivalent carbon centers at both ends of the triple bond, each of which is equally susceptible to nucleophilic attack. This 50–50 distribution of products is confirmed through isotopic...
01:11Aryldiazonium Salts to Azo Dyes: Diazo Coupling
The reaction of weakly electrophilic aryldiazonium (also called arenediazonium) salts with highly activated aromatic compounds leads to the formation of products with an —N=N— link, called an azo linkage. This reaction, presented in Figure 1, is known as diazo coupling and occurs without the loss of the nitrogen atoms of the aryldiazonium salt. Highly activated aromatic compounds such as phenols or arylamines favor the diazo coupling reaction. The coupling generally occurs at the para position.