Slajd 1

Aminy

chlorofil

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Slajd 2

amoniak trietyloamina

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Slajd 3

Wypadkowymomentdipolowy

1° lub 2° aminy:donory lub

akceptory wiązania wodorowego

3° aminy:mogą być wyłącznie

akceptorami wiązania wodorowego

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Slajd 4

Nazewnictwo amin

• Klasyfikacja amin•• 11°°, , 22°° lublub 33°° aminaminyy: pochodne amoniaku, w których

1, 2 lub 3 atomy wodoru zastąpione zostały grupami alkilowymi lub arylowymi

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Slajd 5

••44°° aminaminyy: jon, w którym atom azotu połączony jest z czterema atomami węgla i obdarzony jest ładunkiem dodatnim

+CH3

CH3

CH3 - N-CH3Br-

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Slajd 6

•• aminaminyy alialifatycznefatyczne : aminy, w których atom azotu połączony jest tylko z atomami węgla grup alifatycznych

•• aminaminyy aromataromatyczneyczne : aminy, w których atom azotu połączony jest z jedną lub większą ilością grup aromatycznych

CH3

CH3

CH3 -NH2 CH3 -N

N-H CH2 - N-CH3

CH3 CH3NH2

metyloamina

trimetyloamina

anilina N-metyloanilina N,N-dimetylobenzyloamina

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Slajd 7

•• aminaminyy heterocyheterocyklicznekliczne : aminy, w których atom azotu jest jednym z atomów pierścienia

PyrrolePiperidine Pyrrolidine Pyridine(heterocyclic

aliphatic amines)(heterocyclic

aromatic amines)

NN N NHH H

Piperydyna Pirolidyna(heterocykliczne aminy

alifatyczne)

Pirol Pirydyna (heterocykliczne

aminy aromatyczne)

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Slajd 8

(R)-etylometyloamina (S)-etylometyloaminastan przejściowy

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Slajd 9

(S)-2-butyloamina (R)-2-butyloamina

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Slajd 10

Reakcje amin jako nukleofila

Reakcje amin jako zasady

nukleofil elektrofil

zasada kwas

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Slajd 11

słabsza zasada

mocniejsza zasada

stabilizowana przez grupę alkilową

Zasadowość amin

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Slajd 12

anilinastabilizowana poprzez

nakładanie z pierścieniem

jon aniliniowynie ma stabilizacji

amina alifatyczna

amina aromatyczna

efektnakładania mniej

zasadowa

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Slajd 13

Reakcje amin

Alkilowanie

amina 1° halogenek 1° sól aminy 2°

amina 2°

sól aminy 3°amina 2°

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Slajd 14

Acylowanie

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Slajd 15

Sulfonowanie

sulfonamidchlorek sulfonylu

amina

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Slajd 16

Reakcja diazowania

kwas azotawy protonowany kwas azotawy jon nitrozoniowy

amina 1°N-nitrozoamina

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Slajd 17

N-nitrozoamina protonowana N-nitrozoamina

jon diazoniowy

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Slajd 18

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Slajd 19

∆

∆

przykład

Przykłady wykorzystania związków diazowy

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Slajd 20

Reakcja Sandmeyera

Przykład

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Slajd 21

borofluorek diazoniowy

∆

∆

przykład

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Slajd 22

przykład

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Slajd 23

-H

przykład

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Slajd 24

jon diazoniowy (aktywowany) związek diazowy

oranż metylowy (wskaźnik)

przykład

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Slajd 25

keton lub aldehyd oksym amina 1°

2-pentanon 2-pentamina

benzaldehyd benzyloamina

przykład

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Slajd 26

keton lub aldehyd N-podstawiona imina amina 2°

aceton fenyloizopropyloamina(75%)

przykład

Alkilowanie redukcyjne

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Slajd 27

Utlenianie amin

R NH2 R NH OH R N O R N+

O-

Ooxd oxd oxd

R NH

R

+ H2O2 R N+

R

OH

H + OH- R N

R

OH

+ H2O

R N

R

+ H2O2 R N+

R

OH

R + OH- R N

R

O_

+ H2O

R R

a hydroxylamine a nitrosocompound

hydroksyloamina związeknitrozo

związeknitrowy

utlen. utlen. utlen.

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Slajd 28

Otrzymywanie amin

halogenek lub tosylan

musi być 1° lub 2°

azydek sodu azydek alkilu amina 1°

1-bromo-2-fenyloetan azydek 2-fenyloetylu 2-fenyloetyloamina (89%)

azydek cykloheksylu cykloheksyloamina (54%)

bromek cykloheksylu

przykład

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Slajd 29

halogenek lub tosylan

musi być 1° lub 2°

przykład

nitryl amina(o jeden atom dłuższy łańcuch)

1-bromopropan

butanonitryl 1-butyloamina (70%)

Redukcja nitryli

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Slajd 30

przykład

2-nitropentan 2-aminopentan (85%)

o-nitrotoluen o-toluidyna (90%)

H2/kataliz.

lub aktywny metal i kwas

Redukcja związków nitrowych

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Slajd 31

Przegrupowanie Hofmanna

amid 1° amina

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Slajd 32

Wybrane typy związków zawirających azot

imina sól amoniowa hydroksyloaminaamina

aminotlenek nitrozo nitro

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Slajd 33

Ważne aminy występujące naturalnie

dopaminaneurotransmiter

epinefrynahormon

L-tryptofanaminokwas

piperazynazabija robaki

w jelitach

kwas nikotynowyniacyna, witamina

pirydoksynawitamina B6

histaminarozszerza naczynia

krwionośne

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Slajd 34

Kokainaliście koki

Nikotynatytoń

Meskalinakaktus peyote

Morfinamak lekarski

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Slajd 35

Porfiryna

pierścień porfirynowy

hem

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Slajd 36

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Slajd 37

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