theodori-Chapter_23___Amines-504943111

theodori-Chapter_23___Amines-504943111 - 23-23-1CHAPTER

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Unformatted text preview: 23-23-1CHAPTER 23AMINES23-23-2Structure & ClassificationStructure & ClassificationAmines are classified as: 1, 2, or , 3 amines:1, 2, or , 3 amines:Amines in which 1, 2, or 3 hydrogens of NH3are replaced by alkyl or aryl groups.Methylamine(a 1 amine)Dimethylamine(a 2 amine)Trimethylamine(a 3 amine)CH3- NH2CH3- NHCH3- NCH3CH3CH3:::23-23-3Structure & ClassificationStructure & ClassificationAmines are further divided into aliphatic, aromatic, and heterocyclic amines:AliphaticAliphatic amine:amine:An amine in which nitrogen is bonded only to alkyl groups.Aromatic amine:Aromatic amine:An amine in which nitrogen is bonded to one or more aryl groups.Aniline(a 1 aromatic amine)N-Methylaniline(a 2 aromatic amine)Benzyldimethylamine(a 3 aliphatic amine)NH2N-HCH2-N-CH3CH3CH3:::23-23-4Structure & ClassificationStructure & ClassificationHeterocyclic amine:Heterocyclic amine:An amine in which nitrogen is one of the atoms of a ring.PyrrolePiperidinePyrrolidinePyridine(heterocyclic aliphatic amines)(heterocyclic aromatic amines)NNNHHNH23-23-5Structure & ClassificationStructure & ClassificationExample:Example:Classify each amino group by type.OOC6H5NCH3COOCH3HNHNNCH3H(b)(S)-Coniine(a)Cocaine(S)-Nicotine(c)23-23-6Nomenclature Nomenclature Aliphatic amines: replace the suffix -eeof the parent alkane by -amineamine.1,6-Hexanediamine(S)-1-Phenyl-ethanamine2-PropanamineNH2NH2NH2H2N23-23-7NomenclatureNomenclatureThe IUPAC system retains the name aniline.3-Methoxyaniline(m-Anisidine)4-Methylaniline(p-Toluidine)Aniline4-Nitroaniline(p-Nitroaniline)NH2NH2CH3OCH3NH2NO2NH223-23-8NomenclatureNomenclatureAmong the various functional groups discussed in the text, -NH2is one of the lowest in order of precedence.COOHH2NOHNH2H2NOH4-Aminobenzoic acid2-Aminoethanol(S)-2-Amino-3-methyl-1-butanol23-23-9NomenclatureNomenclatureCommon names for most aliphatic amines are derived by listing the alkyl groups bonded to nitrogen in one word ending with the suffix -amineamine.CH3NH2 NHEt3NNH2TriethylamineDicyclopentylamineMethylaminetert-Butylamine23-23-1010NomenclatureNomenclatureWhen four groups are bonded to nitrogen, the compound is named as a salt of the corresponding amine.Me4N+ Cl -NCH2(CH2)1 2CH3Cl -Ph CH2NMe3OH-+Benzyltrimethyl-ammoniumhydroxideTetramethyammoniumchlorideTetradecylpyridinium chloride(Cetylpyridinium chloride)23-23-1111Chirality of AminesChirality of AminesIf we consider the unshared pair of electrons on nitrogen as a fourth group, then the arrangement of groups around N is approximately tetrahedral.An amine with three different groups bonded to N is chiral and exists as a pair of enantiomers and, in principle, can be resolved.23-23-1212Chirality of AminesChirality of AminesIn practice, however, they cannot be resolved because they undergo pyramidal inversion, which converts one enantiomer to the other.23-23-1313Chirality of AminesChirality of AminesPyramidal inversion is not possible with quaternary ammonium ions, and their salts can be resolved....
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This note was uploaded on 04/02/2011 for the course GENETICS 8383 taught by Professor Love during the Spring '11 term at Rutgers.

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theodori-Chapter_23___Amines-504943111 - 23-23-1CHAPTER

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