Related Experiment Video
Updated: May 15, 2026

A General Method for Detecting Nitrosamide Formation in the In Vitro Metabolism of Nitrosamines by Cytochrome P450s
Published on: September 25, 2017
A further study of acetylacetone nitrosation
Emilia Iglesias1, Isabel Brandariz
1Department of Química Física e E. Q. I. Facultad de Ciencias, Universidad de La Coruña, 15071-La Coruña, Spain. emilia.iglesias@udc.es
Revisiting acetylacetone (AcAc) nitrosation reveals buffers form new nitrosating agents, challenging prior UV-Vis spectroscopy findings. The study confirms no base catalysis, attributing buffer effects to these novel salts.
Area of Science:
- Organic Chemistry
- Chemical Kinetics
Background:
- The nitrosation of acetylacetone (AcAc) is a key organic reaction.
- Previous studies suggested UV-Vis spectroscopy was suitable for monitoring AcAc nitrosation in buffered aqueous acid media.
Discussion:
- This study re-evaluates acetylacetone nitrosation in perchloric acid and chloroacetic acid buffers.
- Contrary to García-Rio et al., UV-Vis spectroscopy is unsuitable for monitoring the reaction under specific conditions ([nitrite] ≪ [acetylacetone]).
- The limited effect of buffers is explained by the formation of nitrosyl chloroacetate salts, which act as alternative nitrosating agents.
Key Insights:
- The formation of nitrosyl chloroacetate, dichloroacetate, and trichloroacetate salts are identified as novel nitrosating agents.
- The previously established mechanism of acetylacetone nitrosation, which does not involve base catalysis, is corroborated.
- The unsuitability of UV-Vis spectroscopy for studying nitrosation under specific buffered conditions is demonstrated.
Outlook:
- Further investigation into the kinetics and mechanisms of these newly identified nitrosating agents.
- Exploring the synthetic utility of nitrosyl chloroacetate salts in organic synthesis.
- Revisiting other nitrosation reactions where buffer effects might be attributed to similar salt formations.
More Related Videos
07:30A Direct, Regioselective and Atom-Economical Synthesis of 3-Aroyl-N-hydroxy-5-nitroindoles by Cycloaddition of 4-Nitronitrosobenzene with Alkynones
Published on: January 21, 2020
06:00One-pot Microwave-assisted Conversion of Anomeric Nitrate-esters to Trichloroacetimidates
Published on: January 15, 2018
Related Concept Videos
2° Amines to N-Nitrosamines: Reaction with NaNO2
Nitrosation of Enols
Alkylation of β-Ketoester Enolates: Acetoacetic Ester Synthesis
Nucleophilic Acyl Substitution of Carboxylic Acid Derivatives
α-Hydroxy Ketones via Reductive Coupling of Esters: Acyloin Condensation Overview
Nitriles to Carboxylic Acids: Hydrolysis