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Blessie Mae R. Encila IV-B.S Chemistry for Teachers Advance Organic Chemistry

Blessie Mae R. Encila IV-B.S Chemistry for Teachers Advance Organic Chemistry. N I TR I LE. R-C N . 01. WINTER. . Nitrile History Nomenclature . Template. A nitrile is any organic compound that has a -C≡N functional group.

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Blessie Mae R. Encila IV-B.S Chemistry for Teachers Advance Organic Chemistry

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  1. Blessie Mae R. EncilaIV-B.S Chemistry for TeachersAdvance Organic Chemistry NITRILE R-CN

  2. 01 WINTER  Nitrile History Nomenclature Template

  3. A nitrile is any organic compound that has a -C≡N functional group. • The prefix cyano- is used interchangeably with the term nitrile in industrial literature. • Nitriles are found in many useful compounds, including • methyl cyanoacrylate • used in super glue • nitrile butadiene rubber • a nitrile-containing polymer used in latex-free laboratory and medical gloves. Nitrile

  4. Nitrile • Organic compounds containing multiple nitrile groups are known as cyanocarbons. • Inorganic compounds containing the -C≡N group are not called nitriles, but cyanides instead. • Though both nitriles and cyanides can be derived from cyanide salts, most nitriles are not nearly as toxic.

  5. Nitrile History • C.W. Scheele in 1782 -He synthesized the first compound of the homolog row of nitriles, which is the nitrile of formic acid, and hydrogen cyanide. -He was able to prepare the very toxic and volatile pure acid. • J. L. Gay-Lussac in 1811 -They prepared the nitrile of benzoic acids, but due to minimal yield of the synthesis neither physical nor chemical properties were determined nor a structure suggested. • Friedrich Wöhler and Justus von Liebig

  6. Nitrile History • Théophile-Jules Pelouze in 1834 -He synthesized propionitrile suggesting it to be an ether of propionic alcohol and hydrocyanic acid. • Hermann Fehling in 1844 -The synthesis of benzonitrile, by heating ammonium benzoate, was the first method yielding enough of the substance for chemical research. He determined the structure by comparing it to the already known synthesis of hydrogen cyanide by heating ammonium formate to his results. He coined the name nitrile for the newfound substance, which became the name for the compound group.

  7. Nitrile Nomenclature Two systems have been adopted by IUPAC: 1. Nitriles derived from open-chain alkanes are named by adding –nitrile as a suffix to the alkane name, with the nitrile carbon numbered C1: 4-Methylpentanenitrile 4,5-dimethylhexanenitrile

  8. Nitrile Nomenclature Two systems have been adopted by IUPAC: 2. Nitriles are named as derivatives of carboxylic acids by replacing the –ic acid or –oic acid with –onitrile, or replacing –carboxylic acid with -carbonitrile. Benzonitrile Acetonitrile 3,3-Dimethylcyclohexanecarbonitrile

  9. 02 Nitrile General Reactions of Nitrile

  10. General Reactions of Nitriles H2O H2O CarboxylicAcid Amide Chemistry of Nitriles LiAlH4 R’MgX Nitrile Ketone Amine

  11. Hydrolysis: Conversion of Nitriles into Carboxylic Acids A nitrile can be hydrolyzed in either basic or acidic aqueous solution to yield a carboxylic acid and ammoniz or an amine H3O+ Or NaOH, H2O Basic hydrolysis of a nitrile --OH Chemistry of Nitriles Dianion H2O Amide --OH --OH NH2- Carboxylate

  12. Reduction: Conversion of Nitriles into Amines A nitrile can be reduced with LiAlH4 to give a primary amine Chemistry of Nitriles H2O LiAlH4 LiAlH4 ether ether Nitrile Imine anion Dianion Amine

  13. Reaction of Nitriles with Organometallic Reagents A nitrile can add a Grignard reagent to give an intermediate imine anion that is further hydrolyzed by water to yield a ketone: Chemistry of Nitriles :R’- +MgX H2O NH3 Nitrile Imine anion Ketone

  14. 03 Nitrile Application

  15. Over 30 nitrile-containing pharmaceuticals are currently marketed for a diverse variety of medicinal indications with more than 20 additional nitrile-containing leads in clinical development. Nitrile

  16. Nitrile • Structure of periciazine, an antipsychotic studied in the treatment of opiate dependence. • Structure of citalopram, an antidepressant drug of the selective serotonin reuptake inhibitor (SSRI) class.

  17. Nitrile • Structure of cyamemazine, an antipsychotic drug. • Structure of fadrozole, an aromatase inhibitor for the treatment of breast cancer.

  18. Nitrile • Structure of letrozole, an oral non-steroidal aromatase inhibitor for the treatment of certain breast cancers.

  19. 04 Nitrile Journal

  20. Nifurtimox Activation by Trypanosomal Type I Nitroreductases Generates Cytotoxic Nitrile Metabolites Belinda S. Hall, Christopher Bot, and Shane R. Wilkinson From the School of Biological and Chemical Sciences, Queen Mary University of London, United Kingdom

  21. The aim of this work was to determine the role of NTRs (trypanosomal type I nitroreductase) in nifurtimoxaction.

  22. 05 Thank You! 

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