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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.

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This lesson defines the leveling effect in acidic and basic solutions and its role in aqueous and non-aqueous solutions. It is essential to understand the competing nature of various species in a chemical system.
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Introduction
Alkylation of terminal alkynes with primary alkyl halides in the presence of a strong base like sodium amide is one of the common methods for the synthesis of longer carbon-chain alkynes. For example, treatment of 1-propyne with sodium amide followed by reaction with ethyl bromide yields 2-pentyne.

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Alkynes are unsaturated hydrocarbons characterized by the presence of carbon-carbon triple bonds and have a general formula CnH2n-2. The nomenclature of alkynes follows a set of rules similar to alkanes and alkenes; however, alkynes bear the suffix "-yne" instead of "-ane" or "-ene." There are two approaches to naming alkynes:

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Preparation and In Vivo Use of an Activity-based Probe for N-acylethanolamine Acid Amidase

Preparation and In Vivo Use of an Activity-based Probe for N-acylethanolamine Acid Amidase

Published on: November 23, 2016

Provisional Advisory Levels (PALs) for acrylonitrile.

Susan Goldhaber¹, David Dorman, Donald Gardner

¹Toxicology and Hazard Assessment Group, Environmental Sciences Division, Oak Ridge National Laboratory, Oak Ridge, Tennessee, USA.

Inhalation Toxicology

|October 16, 2009

Summary

This summary is machine-generated.

Provisional Advisory Levels (PALs) for acrylonitrile exposure were established for drinking water and inhalation. These health-based guidance values address varying exposure durations and toxicological severity.

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Area of Science:

Environmental Health Risk Assessment
Toxicology
Public Health

Background:

Acrylonitrile is a chemical with potential exposure risks through drinking water and inhalation.
Provisional Advisory Levels (PALs) are health-based guidance values used to assess chemical safety.
Previous research established methodologies for deriving PALs, detailed in accompanying publications.

Purpose of the Study:

To apply Provisional Advisory Level (PAL) protocols to acrylonitrile.
To establish health-based guidance values for various exposure durations and routes.
To inform public health decisions regarding acrylonitrile exposure.

Main Methods:

Utilized experimental data, primarily from animal studies, for acrylonitrile toxicity.
Developed three levels of PALs (PAL 1, PAL 2, PAL 3) reflecting increasing toxic effect severity.
Calculated PALs for 24-hour, 30-day, 90-day, and 2-year exposure durations via oral and inhalation routes.

Main Results:

Established oral PALs for 24-hour, 30-day/90-day, and 2-year exposures, with specific values for PAL 1, 2, and 3.
Established inhalation PALs for 24-hour, 30-day/90-day, and 2-year exposures, with specific values for PAL 1 and 2.
Noted insufficient data to recommend PAL 3 values for 30-day, 90-day, and 2-year inhalation exposures.

Conclusions:

PALs for acrylonitrile were successfully derived for various exposure scenarios.
The established PALs provide crucial guidance for assessing potential health risks from acrylonitrile.
Data limitations were identified for specific long-term inhalation exposure scenarios.