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Acidity of 1-Alkynes

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.

Structures of Carboxylic Acid Derivatives

Structures of Carboxylic Acid Derivatives

Structure 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...

Alkylation of β-Ketoester Enolates: Acetoacetic Ester Synthesis

Alkylation 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.

Diazonium Group Substitution: –OH and –H

Diazonium 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.

Oxymercuration-Reduction of Alkenes

Oxymercuration-Reduction of Alkenes

Oxymercuration–reduction of alkenes is one of the major reactions converting alkenes to alcohols. It involves the hydration of alkenes with mercuric acetate in a mixture of tetrahydrofuran and water, forming an organomercury adduct. This is followed by a demercuration step in which the adduct is reduced to an alcohol using sodium borohydride.

Indirect-Acting Cholinergic Agonists: Chemistry and Structure-Activity Relationship

Indirect-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...

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Related Experiment Video

Updated: May 13, 2026

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives

Published on: January 19, 2016

4-Meth-oxy-benzamidinium acetate.

Simona Irrera¹, Gustavo Portalone

¹Chemistry Department, "Sapienza" University of Rome, P.le A. Moro, 5, I-00185 Rome, Italy.

Acta Crystallographica. Section E, Structure Reports Online

|March 8, 2013

Summary

Researchers synthesized a novel ionic compound from 4-methoxybenzamidine and acetic acid. Crystal analysis revealed a unique 1D structure formed by hydrogen bonds between the components.

Area of Science:

Crystal Chemistry
Organic Synthesis
Supramolecular Chemistry

Background:

Benzamidine derivatives are important in medicinal chemistry and materials science.
Understanding the supramolecular assembly of ionic organic compounds is crucial for designing new materials.

Purpose of the Study:

To synthesize and characterize a new ionic compound derived from 4-methoxybenzamidine.
To investigate the crystal structure and hydrogen bonding interactions of the synthesized salt.

Main Methods:

Synthesis of the title compound via reaction of 4-methoxybenzamidine with acetic acid.
Single-crystal X-ray diffraction analysis to determine the molecular and crystal structure.

Main Results:

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The title compound, C8H11N2O(+)·CH3CO2(-), was successfully synthesized.

The crystal structure exhibits a one-dimensional arrangement driven by N-H(+)⋯O(-) hydrogen bonds.

The amidinium group shows a dihedral angle of 11.65(17)° with the benzene ring plane.

Conclusions:

The synthesis yielded a novel ionic compound with potential applications in materials science.
The observed hydrogen bonding network dictates the formation of a 1D supramolecular architecture.
Structural insights provide a basis for further exploration of related benzamidine salts.