Conjugated Nitrile

A conjugated nitrile is an organic compound in which a nitrile group, containing a carbon-nitrogen triple bond, is directly connected to another unsaturated π system, commonly a carbon-carbon double bond. This arrangement allows π electrons to delocalize through the connecting atoms, altering electron distribution, polarity, and chemical reactivity. Conjugated nitriles can participate in carbon-carbon bond-forming reactions and nucleophilic additions, making them useful building blocks in organic synthesis and materials chemistry. Their electronic behavior also provides a basis for studying structure-reactivity relationships and for designing molecules with controlled optical and electronic properties.

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JoVE Core - Organic Chemistry

Preparation of Nitriles

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2023

One of the common methods to prepare nitriles is the dehydration of amides. This method requires strong dehydrating agents like phosphorous pentoxide or boiling acetic anhydride for converting amides to nitriles. Another reagent namely, thionyl chloride also accomplishes the dehydration of amides, where amide acts as a nucleophile. The first step of the mechanism involves the nucleophilic attack by the amide on the thionyl chloride to form an intermediate. In the next step, the electron pairs...

Conjugated Proteins

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2020

Simple proteins and protein complexes contain only amino acids. In contrast, many other proteins, called conjugated proteins, covalently bond with non-protein moieties. Nucleoproteins are protein complexes that contain nucleic acids, categorized as deoxyribonucleoproteins (DNPs) or ribonucleoproteins (RNPs) respectively. The nucleosome is a typical example of a DNP where nuclear DNA is associated with histone proteins. The major antigen for the Covid-19 virus SARS-CoV is an RNP that is critical...

Nitriles to Carboxylic Acids: Hydrolysis

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2025

Nitriles undergo acid-catalyzed hydrolysis or base-catalyzed hydrolysis to form a carboxylic acid. These reactions proceed via an amide intermediate. The acid-catalyzed mechanism involves the protonation of the nitrogen atom to make the carbon atom more susceptible to nucleophilic attack. The second step involves the nucleophilic attack by water on the nitrile carbon atom. Subsequently, deprotonation of the oxygen atom gives a tautomeric form of an amide, and protonation of the nitrogen forms...

IR Frequency Region: Alkyne and Nitrile Stretching

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2024

Both alkyne (C≡C) and nitrile (C≡N) functional groups contain triple bonds and show stretching absorptions around the wavenumber range of 2100 to 2300 cm−1 in the diagnostic region of the IR spectra. Comparing the stretching vibrational frequency of C≡C triple bonds with that of double and single bonds, it is evident that C≡C triple bonds exhibit a higher stretching frequency than C=C double and C–C single bonds. Similarly, the C≡N triple bond exhibits higher stretching absorption than the C=N...

Nitriles to Ketones: Grignard Reaction

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2025

Organomagnesium halides, commonly known as Grignard reagents, convert nitriles to ketones and proceed through a nucleophilic acyl substitution. Nitriles react with a Grignard reagent, followed by an aqueous acid, to yield ketones. The reaction introduces a new carbon–carbon bond. The alkyl–magnesium bond in the Grignard reagent is highly polar, so the alkyl carbon develops a carbanionic character and acts as a nucleophile. The mechanism begins with a nucleophilic attack by the Grignard reagent...

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