tailieunhanh - Lecture Organic chemistry: Chapter 19 - L. G. Wade, Jr.

Amines are organic derivatives of ammonia with one or more alkyl or aryl groups bonded to the nitrogen atom. As a class, amines include some of the most important biological compounds. Amines serve many functions in living organisms, such as bioregulation, neurotransmission, and defense against predators. This chapter draw and name amines, and use spectral information to determine their structures; compare the basicity of amines with other common bases, and explain how their basicity varies with hybridization, aromaticity, resonance, and induction. | Chapter 19 Copyright © 2010 Pearson Education, Inc. Organic Chemistry, 7th Edition L. G. Wade, Jr. Amines Chapter 19 Biologically Active Amines The alkaloids are an important group of biologically active amines, mostly synthesized by plants to protect them from being eaten by insects and other animals. Many drugs of addiction are classified as alkaloids. Chapter 19 Biological Activity of Amines Dopamine is a neurotransmitter. Epinephrine is a bioregulator. Niacin, Vitamin B6, is an amine. Alkaloids: nicotine, morphine, cocaine Amino acids Chapter 19 Classes of Amines Primary (1 ): Has one alkyl group bonded to the nitrogen (RNH2). Secondary (2 ): Has two alkyl groups bonded to the nitrogen (R2NH). Tertiary (3 ): Has three alkyl groups bonded to the nitrogen (R3N). Quaternary (4 ): Has four alkyl groups bonded to the nitrogen and the nitrogen bears a positive charge(R4N+). Chapter 19 Examples of Amines Primary (1º) Secondary (2º) Tertiary (3º) . | Chapter 19 Copyright © 2010 Pearson Education, Inc. Organic Chemistry, 7th Edition L. G. Wade, Jr. Amines Chapter 19 Biologically Active Amines The alkaloids are an important group of biologically active amines, mostly synthesized by plants to protect them from being eaten by insects and other animals. Many drugs of addiction are classified as alkaloids. Chapter 19 Biological Activity of Amines Dopamine is a neurotransmitter. Epinephrine is a bioregulator. Niacin, Vitamin B6, is an amine. Alkaloids: nicotine, morphine, cocaine Amino acids Chapter 19 Classes of Amines Primary (1 ): Has one alkyl group bonded to the nitrogen (RNH2). Secondary (2 ): Has two alkyl groups bonded to the nitrogen (R2NH). Tertiary (3 ): Has three alkyl groups bonded to the nitrogen (R3N). Quaternary (4 ): Has four alkyl groups bonded to the nitrogen and the nitrogen bears a positive charge(R4N+). Chapter 19 Examples of Amines Primary (1º) Secondary (2º) Tertiary (3º) Chapter 19 Common Names Chapter 19 Amine as Substituent On a molecule with a higher priority functional group, the amine is named as a substituent. Chapter 19 IUPAC Names Name is based on longest carbon chain. -e of alkane is replaced with -amine. Substituents on nitrogen have N- prefix. 3-bromo-1-pentanamine N,N-dimethyl-3-hexanamine N H 2 C H 2 C H 2 C H C H 2 C H 3 B r C H 3 C H 2 C H C H 2 C H 2 C H 3 N ( C H 3 ) 2 Chapter 19 Aromatic Amines In aromatic amines, the amino group is bonded to a benzene ring. Parent compound is called aniline. Chapter 19 Heterocyclic Amines When naming a cyclic amine the nitrogen is assigned position number 1. Chapter 19 Structure of Amines Nitrogen is sp3 hybridized with a lone pair of electrons. The angle is less than . Chapter 19 Interconversion of Chiral Amines Nitrogen may have three different groups and a lone pair, but enantiomers cannot be isolated due to inversion around N. Chapter 19