Cyano-

Definition

The prefix 'cyano-' is derived from the Greek word 'kyanos,' meaning 'blue.' In the context of organic chemistry, it refers to a functional group or substituent containing a carbon-nitrogen triple bond (C≡N), known as the cyano or nitrile group. This prefix is commonly used in the naming and identification of compounds containing this functional group.

5 Must Know Facts For Your Next Test

1. The cyano group is a highly polar functional group, with a partial positive charge on the carbon and a partial negative charge on the nitrogen, making it susceptible to nucleophilic attack.
2. Compounds containing the cyano group are often used as precursors in the synthesis of other organic compounds, such as carboxylic acids, amides, and amines.
3. Nitriles are generally less reactive than their corresponding carboxylic acids, but they can undergo nucleophilic addition-elimination reactions to form new compounds.
4. The cyano group is a common substituent in many pharmaceutical and agrochemical compounds, as it can impart specific physical and biological properties.
5. The presence of the cyano group in a compound can significantly affect its physical and chemical properties, such as boiling point, solubility, and reactivity.

Review Questions

• Explain the role of the cyano group in the naming of carboxylic acids and nitriles.
  • The cyano group (−C≡N) is a key functional group in the naming of both carboxylic acids and nitriles. When the cyano group is present, it is indicated by the prefix 'cyano-' in the name of the compound. For carboxylic acids, the cyano group can be introduced by removing the hydroxyl group (−OH) and replacing it with the cyano group, forming a nitrile. Conversely, nitriles can be converted to carboxylic acids by hydrolysis, which involves the addition of water and the replacement of the cyano group with a carboxyl group (−COOH). The presence of the cyano group significantly influences the reactivity and properties of these organic compounds.
• Describe the nucleophilic addition-elimination reaction mechanism involving the cyano group.
  • The cyano group can undergo nucleophilic addition-elimination reactions, where a nucleophile adds to the carbon of the C≡N triple bond, followed by the elimination of a leaving group. This reaction mechanism is commonly observed in the conversion of nitriles to other functional groups, such as amides or carboxylic acids. The nucleophilic addition step involves the attack of the nucleophile on the partially positive carbon of the cyano group, forming a tetrahedral intermediate. This is followed by the elimination of a leaving group, such as a cyanide ion, resulting in the formation of a new compound containing a different functional group. The ability of the cyano group to participate in these types of reactions is crucial in the synthesis of various organic compounds.
• Evaluate the importance of the cyano group in the design and development of pharmaceutical and agrochemical compounds.
  • The cyano group is a versatile functional group that is widely used in the design and development of pharmaceutical and agrochemical compounds. Due to its polarity and ability to participate in various chemical reactions, the cyano group can be strategically incorporated into organic molecules to impart specific physical and biological properties. In the pharmaceutical industry, compounds containing the cyano group may exhibit improved solubility, metabolic stability, or target-specific binding, making them valuable in the development of new drug candidates. Similarly, in the agrochemical field, the cyano group can be used to enhance the potency, selectivity, or environmental fate of pesticides and herbicides. The presence of the cyano group can significantly influence the overall efficacy, safety, and commercial viability of these important classes of chemical compounds. Consequently, a deep understanding of the reactivity and applications of the cyano group is crucial for chemists working in the pharmaceutical and agrochemical industries.

Related terms

Nitrile: A functional group consisting of a carbon-nitrogen triple bond (C≡N), also known as the cyano group.

Carboxylic Acid: An organic compound containing a carboxyl group (−COOH), which can be converted to a nitrile by removing the hydroxyl group and replacing it with a cyano group.

Nucleophilic Addition-Elimination: A reaction mechanism involving the addition of a nucleophile to the carbon of the cyano group, followed by the elimination of a leaving group, resulting in the formation of a new compound.