Chemistry Organic Building Blocks Nitriles
Any organic compound that contains a −C≡N functional group is called a nitrile in organic chemistry. The term "cyano-" is often used interchangeably with "nitrile" in industrial literature.
In nitriles, the sp hybridization of the triply bonded carbon results in a linear N−C−C geometry, while the C−N distance, which is consistent with a triple bond, is short at 1.16 Å.
Nitriles exhibit high dipole moments, indicating their polar nature, and when in the liquid state, they possess high relative permittivities.
Nitrile groups in organic compounds can undergo a variety of reactions depending on the reactants or conditions. A nitrile group can be hydrolyzed, reduced, or ejected from a molecule as a cyanide ion.
Pharmaceuticals containing nitriles are of various types, ranging from vildagliptin, an antidiabetic medication, to anastrozole, which is considered the standard for treating breast cancer. The nitrile group in these pharmaceuticals often mimics the functional groups found in enzyme substrates, while in other cases it enhances water solubility or reduces the susceptibility to oxidative metabolism in the liver.
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2-(3-Hexyl-4-oxothiazolidin-2-ylidene)malononitrile
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3-(1-(2,6-Diisopropylphenyl)-1H-imidazol-2-yl)benzonitrile
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2-Amino-3,3-dimethylbutanenitrile hydrochloride
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1-Amino-1-cyclopropanecarbonitrile hydrochloride
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1-Cyclopropyl-4-oxocyclohexanecarbonitrile
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Potassium 1-cyano-3-ethoxy-2,3-dioxopropan-1-ide
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Methyl 4-cyanobicyclo[2.2.2]octane-1-carboxylate