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Nitrile Properties

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    5362
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    The electronic structure of nitriles is very similar to that of an alkyne with the main difference being the presence of a set of lone pair electrons on the nitrogen. Both the carbon and the nitrogen are sp hydridized which leaves them both with two p orbitals which overlap to form the two \(\pi\) bond in the triple bond. The R-C-N bond angle in and nitrile is 180° which give a nitrile functional group a linear shape.

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    The lone pair electrons on the nitrogen are contained in a sp hybrid orbital which makes them much less basic and an amine. The 50% character of an sp hybrid orbital close to the nucleus and therefore less basic compared to other nitrogen containing compounds such as amines.

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    The presence of an electronegative nitrogen causes nitriles to be very polar molecules. Consequently, nitriles tend to have higher boiling points than molecules with a similar size.

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    Nitrile Properties is shared under a CC BY-NC-SA 4.0 license and was authored, remixed, and/or curated by LibreTexts.

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