PHARMACEUTI

CALORGANI
C
CHEMISTRY–I
I
UNI
TII
UNI
TII A.Phenols* 10Hours
B.AromaticAmi nes*
C.AromaticAcids*
Aromat
icAmines*-Basi ci
tyofamines,
eff
ectofsubst
it
uent
sonbasi
ci
ty,
and
synt
het
icusesofaryl
di azoni
um salt
s
Note:Needtost
udy
,gener
almet
hodsofpr
epar
ati
onandr
eact
ionsofcompoundssuper
scr
ipt
edwi
th
ast
eri
sk(*)
.

Ar
omat
icAmi
nes
Ami nesconst i
tut
eani mpor tantcl assofor ganiccompoundsder ivedby
repl
acingoneormor ehy drogenat omsofammoni amol eculebyal kyl
group(s)( al
ky l
amines)and/ orar ylgr oup( s)(aromat icami nes).Innat ure,
theyoccuramongpr ot eins,v i
tami ns,al kaloids( e.
g.l ikeopi um alkal
oids
mor phine,codei ne,ni cotine al kaloid oft obacco,et c.)and hor mones.
Syntheticexampl esincludepol ymer s, dyestuffsanddr ugs.Twobi ol
ogicall
y
acti
v e compounds,namel y adr enal i
ne and ephedr ine,bot h contai
ning
secondar yami nogr oup,ar eusedt oi ncreasebl oodpr essure.Nov ocain,a
syntheticami nocompound, isusedasananaest heti
ci ndent istr
y.Benadr yl
,
a wel lknown ant i
histami nic dr ug al so cont ai
ns t ertiar
yami no group.
Quat er
naryammoni um sal tsar eusedassur factants.Di azonium saltsare
i
ntermedi ates int he pr eparation ofa v ar i
etyofar omat i
c compounds
i
ncludingdy esandst artingmat erialint hepr eparati
onofmanysubst it
uted
benzenecompounds( bot hinlabor at oryandi nindustry).

Ami nes can be consi

der
ed as der
ivat
ives ofammoni
a,obtained by
repl
acementofone, t
woorall
thet
hreehydrogenat
omsbyalky
land/orary
l
groups.Forexample:

Funct
ional
group:
PHARMACEUTI
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PHARMACEUTI
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CHEMISTRY–I
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Cl
assi
fi
cat
ionofAmi
nes:

 Primary(1o)ami ne:onealkylorary
l(C6H5NH2)gr oupat
tachedt othe
ni
trogenat om.
 Secondar y(2o)amine:twoalkylorarylgroupatt
achedtot henitr
ogen
atom.
 Terti
ary(3o)ami ne:t
hreealkyloraryl
groupat t
achedtothenitrogen
atom.
 Quaternary(4o)amine: anioninwhichni t
rogenisbondedt of
oural ky
l
orarylgroupsandbear saposi ti
vechar ge.

Aminesaref ur
therdivi
dedint
oali
phati
c,ar
omati
c,andheter
ocycl
ic
amines:Ali
phati
cami ne:Anamineinwhichni
tr
ogenisbondedonlyto
al
kylgroups.Aromaticamine:Anamineinwhi
chnitr
ogenisbondedto
oneormor earylgroups.

Het
erocy
cli
cami
ne:
Anami
nei
nwhi
chni
tr
ogeni
soneoft
heat
omsofar
ing.
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Nomencl
atur
e:

Commonnames:-formedf r
om thenamesoft heal ky
lgroupsbondedto
ni
trogen,
fol
l
owedbythesuff
ix–amine.-thepr
efixesdi-
,tr
i-
,andtet
ra-ar
e
usedtodecr
ibet
wo,
threeorfouri
dent
ical
substi
tuents.

I
UPACnames

Al
i
phat
icami
nes:
repl
acet
hesuf
fi
x-eoft
hepar
ental
kaneby

–ami
ne.ORsi milartothatalcohols
t helongestcontinuouschainofcarbonatomsdet er
minetherootname.
t he–ei nalkanenamei schangedto–amine,andanumbershows
thepositi
onoft heami nogroupalongthechain.
 othersubstit
uentsont hecarbonchainaregivennumbers,andt
he
prefi
xN-isusedf oreachsubstit
uentonnit
rogen.
PHARMACEUTI
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 Theprefi
x‘amino’
isusedtoi ndi
catet
hepresenceofan–NH2
groupinamoleculecontai
ningthanonefunct
ional
groupOR
 Amongt hevar
iousfuncti
onal gr
oups,
-NH2isoneofthelowesti
n
orderofpr
ecedence.Forexampl e,

Ar
omat
icami
nes:

 Ar
omat
icamineshaveanami
negroup(-
NH2)attacheddi
rect
lyt
othe
ar
omat
icr
ing.
 Ar
omat
icaminesknownasar
ylami
nes.Exampl
es,

Compoundswit
htwo–NH2groupsarenamedbyaddingthesuf
fi
x
‘
diami
ne’tot
henameoft
hecorrespondi
ngal
kaneoraromati
c
compounds.
PHARMACEUTI
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THEBASI
CITYOFAMI
NES

Ami
nescanactas:

 anucleophi
le(
aLewisbase)becauseit
slonepairnonebonding
el
ectr
onscanf or
m abondwi t
hanelect
rophi
le.
 aBrønsted-
Lowrybasebecausei
tcanacceptapr ot
onfrom aprot
on
aci
d.

Gener
alReact
ion: B+H+→ +BH(conj
: ugat
eaci
d)

 Thebasici
tyoftheami nesdependsont heabili
tyofthel
onepai r
nonebondingelectronsatnitr
ogenat om toform bondwithanacid.
 Themor eeasierthelonepairelectr
onsf or
medbondwi t
ht heaci
d,
wil
lmaket heaminesast rongerbase.
 Theequili
bri
um constantforthisreacti
oniscall
edbase-dissoci
ati
on
const
ant,symbolizedbyKb.
+ +
 Kb=[BH ]/[:
B][H ](Str
ongbasehav ehigherval
uesofKb)
 pKb=-logKb( Str
ongerbasehav esmallerval
uesofpKb)

:
NH3 (
1°)R- (
2°)R-NH- (
3°)R3-
NH2 R N
pKb 4.
74 3.
36 3.
27 4.
19
pKa 9.
26 10.64 10.73 9.
81

Not
e:St
rongbaseshav
eweakconjugateacids,
andweakbaseshav
est
rong
conjugateacids.
PHARMACEUTI
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Fact
orsThatAf
fectt
heBasi
cit
yoft
heAmi
nes

Aminesar ebasi cbecauset heypossessapai rofunshar edel ectrons,

whi
cht heycanshar ewi thotherat oms.Theseunshar edelect ronscr eate
anelectrondensi t
yar oundt heni t
rogenat om.
 Thegr eatertheel ectr
ondensi t
y ,t
hemor ebasi cthemol ecule.
 Gr oups t hatdonat e orsuppl y electr
ons ( by means ofposi t
ive
i
nduct i
veef fect)willi
ncreaset hebasi ci
tyofami neslikeal ky lgroups
(-CH3,et c.)whi l
egr oupst hatdecr easet heel ectrondensi tyl i
ke- NO2
etc.,(bymeansofnegat ivei nduct i
veef fect)ar oundt heni tr
ogen
decr easet hebasi cit
yoft hemol ecule.
 Duet othispr oper t
yoft heal kylgroup( electron-
donat inggr oupsuch
asCH3-andCH3CH2- )at tachedt ot heni tr
ogenoft heami ne,t he
electrondensi t
yar oundt heni trogenat om increasesandi tsel ectron
releasingabi li
tyincreasest oo.
 Duet ot hegr eaterandeasi erreleaseofel ectronsi ntheal kylami ne,
themol eculebecomesmor ebasi cthanammoni a.
t heor derofbasi ci
ty:3>2>1>NH3

 Wher eas i n ammoni a,no such r el

easing gr oup at tached.So,
obviouslyt hebasicit
yofammoni aismuchl esst hant hatofanal kyl
amine.
Incompar ison, t
hebasicityoft healiphaticaminesi.e.terti
aryami nest obe
thegreatest ,fol
lowedbysecondar yami neandt henpr i
mar yami ne.BUT
THISI SNOTSO.Theor derofbasi cityisNH3 <pr imar yami ne~t ert
iar
y
amine<secondar yaminer espectiv
el ybecauseofduet o
Steri
chindr ance:
 Thesi zeofanal kylgr oupismor ethanthatofahy drogenat om.
 So,anal kyl gr
oupwoul dhindert heatt
ackofahy drogenat om, thus
decreasingt hebasicityofthemol ecul
e.
 Themor et henumberofal kylgroupsattached, l
esserwi l
l beit
s
PHARMACEUTI
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basi
cit
y.
PHARMACEUTI
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 So, t
hedecr easingor derofbasicit
ywi l
lbe:Pri
mar yamine>
secondar yami ne>t erti
aryamine.
Hy
drogenbondi ngorSol vati
onef f
ects:
 Ami nesar efairl
ystrongbaseandt hei
raqueoussol uti
onsar
ebasic.
 Thedi f
ferencesi nthebasi ci
tyorderinthegasphaseandaqueous
soluti
onsar et heresultofsolvati
oneffects(hydrogenbondi
ng).
 Anami necanabst ractapr otonfrom water,gi
vinganammoni um i
on
andahy droxideion.

+ -
Kb=[
RNH
3 ][
OH]/[
RNH]

Inwat er,t
heammoni um sal t
sofpr imaryandsecondaryaminesundergo
solvati
oneffects(duet ohydrogenbondi ng)t
oamuchgr eat
erdegr eet
han
ammoni um saltsoft erti
aryami nes.Thesesolvati
oneff
ect
si ncr
easethe
electr
on densityon t he ami ne nit
rogen to a gr
eat
erdegree than t
he
i
nduct i
veeffectofalkylgroups.

Whenami nesaredissol
vedinwat er
,theyform pr
otonatedami nes.Al
so,
t
henumberofpossi bi
li
ti
esofhydrogenbondingfor
mat i
oni ncr
eases.Mor
e
t
henumberofhy drogenbonding,moreisthehydrati
ont hatisrel
easedi
n
t
heprocessofthef
or mati
onofhy dr
ogenbonds.

Themor ethehy dr
ati
onenergyofthemolecul
e,moreisthest
abil
it
yoft he
amine.Experimentshaveindi
cat
ed,inter
msofhy drat
ionenergy
,thatthe
ter
tiar
yami nesaret heleastst
ablefoll
owedbyt hesecondaryami nes
fol
lowedbyt hepri
maryamines.

Thiscanbeexpl ainedont hebasi

softhef
oll
owi
ng
react
ions.I
npr i
mar yami ne:RNH2+H
3 2O→ RNH++OH-
I
nsecondar yami ne:R2NH+H2O→ R22NH++
OH-Interti
aryami ne:R3N+H2O→ R2NH++
OH-
PHARMACEUTI
CALORGANI
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CHEMISTRY–I
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TII
So,t henumberofhy drogenbondspossi blewhenprimar
yaminesare
dissolv
ed i
n wateristhegr eat
est,implyi
ng t
hattheyaremoststabl
e
speciesofamine,t
hel
eastbeingthetert
iar
yamines.

Conclusi
on:Thecombinedeffectofthepushi
ngeff
ectofthealky
lgroup
(+Ieff
ect)
,st
eri
chindr
anceandt hesal
vat
ionofami
nescausesthebasici
ty
ordertobe:(
basi
cit
yofter
ti
aryisalmostt
hesameasthatofpri
mary).

NH3<pr
imar
yami
ne~ t
ert
iar
yami
ne<secondar
y

ami
neAr
omat
icAmi
nes:

Aromat i
cami nesar el essbasi ct hanal iphaticami nesand
ammoni a.Reason: -
 pKbv al
ueofani l
ine( pKb: 9.
4)i squi t
ehi gherthanammoni a( pKb: 4.7)
.
Iti
sbecausei nani l
ineorot herar y
lami nes,the-NH2gr oupi sat tached
dir
ectlytothebenzener ing.Itresul t
sint heunshar edel ectronpai ron
nit
rogenat om t obei nconjugat ion( Thel onepairofel ectronsont he
nit
rogenat om isdel ocalisedi ntothebenzener ingont ot heor thoand
para posibiti
ons)wi t
ht hebenzener i
ng and thusmaki ng i tl ess
avail
ableforpr otonat i
on.
I ncaseofar ylamines,t her eactioni sshi ft
edt owardt hel eftand
makesani li
neaweakerbaset hanammoni aorali
phat i
cami nes.
I fwewr it
edi fferentr esonatingst ructuresofani l
ine,wewi llfindt hat
anil
ineisar esonancehy bri
doft hef oll
owi ngfivestructures:

Butf
orani
l
ini
um i
onnoot
herr
esonat
ingst
ruct
uresar
epossi
ble.
PHARMACEUTI
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TII
Weknow thatgreat
erthenumberofr esonat
ingstructur
es,gr
eateristhe
st
abil
it
y.Thusyoucaninferthatani
l
ineismor est
abl ethanani
li
nium i
on.
Hence,theprot
onaccept abi
li
tyorthebasicnatur eofanili
neorot her
ar
omat i
camineswouldbelessthant
hatofammoni a.

Otherf actor
(s)to consi
derincomparisoni st hatt
hegreat
erel
ectr
on-
2
withdrawinginduct
iveeffectoft
hesp- hybri
dizedcarbonofanar
omatic
3
ami necompar edwi t
ht hatofthesp-hy br
idi
zedcar bonofanal
iphat
ic
ami ne.

Anil
ine i
s subst
ant
ial
lyless basi
ct han methylamine,as i
s evi
dentby
l
ookingatthepKav aluesforthei
rrespect
iveammoni um conj
ugateaci
ds
(r
emembert hatthelowerthepKaoft heconjugateacid,t
heweakerthe
base).

Wor
kingExampl
e1:
Compar
ethebasi
cit
yofani
l
inewi
thcy
clohexy
lami
ne

In Anil
ine (Arylamines),the lone pairon ni tr
ogen ( which i sf r
ee f
or
prot
onat i
on in a cy cl
ohexylamines)is presenti n conjugation withthe
benzene r ing, so ani li
ne can' tl ose el ectr
ons as easi l
y as a
cycl
ohexy l
ami nescan.Thebasi cit
yofami nesi sduet otheni trogenofthe
aminedonat ingi t
slonepai rofelectr
ons.Sor esonancest abi l
izedamines
arelessbasiccompar edtonon-conjugat
edami nes(alky
lami nes).
PHARMACEUTI
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Incaseofsubst
it
utedanil
ine,i
tisobser
vedthatelect
ronrel
easi
nggroups
l
ike–OCH3,–CH3 i ncr
easebasicstr
engthwhereaselectr
onwi t
hdr
awing
groupsli
ke–NO2,–SO3H, –COOH,-CHO,&–X( X:hal
ogen)decr
easeitbya
combinati
onofr
esonanceandinducti
veeff
ects.

Anythi
ngort
hototheamine,nomat terwhetheritiselectr
ondonati
ngor
wit
hdrawi
ng,wil
ldecr
easet hebasicit
yoft hear omat i
camine.Thisi s
becauseoftheort
hoeffect
,whi chisbasicall
yst eri
cs.Theprotonat
ed
aminewil
lhaveagr
eat
erster
icint
eracti
onwiththeor t
hogroup,
soitwill
be
l
essstabl
e.

Wor
kingExample2:Compar
ethebasi
cit
yof4-
met
hoxyani
l
inewi
th4-
ami
nobenzal
dehy
de.

Inthecaseof4- methoxyani li
ne( t
hemol eculeont heleftsideofthefigure
abov e),t
helonepairont hemet hoxygroupdonat eselectr
ondensitytot he
aromat i
csy stem,andar esonancecont ri
but orcanbedr awni nwhicha
negat i
vechargei spl acedont hecarbonadj acenttot henitr
ogen,whi ch
makest helonepairoft henitrogenmor er eactiv
e.Inef f
ect,themethoxy
groupi s'pushing'electrondensi t
ytowar dst heni t
rogen.Conv er
sely
,t he
aldehydegroupont her i
ght-si
demol ecul
ei s'pulli
ng'elect
rondensityaway
fr
om t henit
rogen,decr easi
ngi t
sbasicit
y.

Theser esonanceeffectsarepossi bl
ewhent hesubstit
uentislocatedat
theorthoorpar aposit
ion,butnotatthemet aposit
ionbecausecannotdo
thi
skindofr esonanceatthemet aposi t
ion.Forexample:3-
nitr
oanil
ineisa
str
ongerbaset han4- ni
tr
oanil
ineduet onon- r
esonanceeffectlonepair
remai
nswi t
hami nefordonati
on/reacti
on.
PHARMACEUTI
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Ov
eral
l

React
ionsofAmi
nes:
1.React
ionofaminesandaci
dwil
lgi
veaminesal
t.
Ami nesal
t:-composedoftwot
ypesofi
ons:i
)thepr
otonat
edami
necat
ion
(anammoni um i
on)ii
)ani
onderi
vedf
rom t
heacid
PHARMACEUTI
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2.React
ionwi thnitr
ousacid:
 Nitrousacid( HNO2)isunst abl
eandi spreparedinsit
ubyt he
reactionofdi l
uteHCl ordil
uteH2SO4wi thsodium nit
ri
tei nthe
absenceofheat .
NaNO2( s)+HCl (
aq)→ NaCl (
aq)+O=N- OH( aq)ni
trousacid
 Nitrousacidcanbeusedt odif
ferenti
ateprimary,
secondar yandt ert
iar
yaliphati
cami nes.
 Primar yaromat i
cami nesreactwithcoldHNO2anddi ssolvedin
diluteHCl at0-5°Cwi l
lproduceddiazonium salt.Whent his
col dsalt
sheat edatroom temperat ur
e,nit
rogengaswi ll
ev olv
ed

 Terti
aryaromati
cami nesr eact
swi t
h nit
rousacid byundergoing
substi
tuti
on atthe para posit
ion oft he benzene r
ing tof or
m
+
ni
trosoanil
inewhi
chi say ellow preci
pit
ate.Here,NO i saweak
el
ectrophi
leandpar
ti
cipat
esi nElect
rophi
li
cAr omati
cSubsti
tut
ion.

Format
ionofNO+f
rom HNO2:
Step1:
Prot
onat
ionofHNO2&St
ep2:
Lossof
H2O.
PHARMACEUTI
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3.Acylati
on:Al i
phatic and aromat ic pr
imaryand secondar yami nes
reactwi t
h acid chlorides,anhy dri
des and esters bynucl eophi
li
c
substit
uti
onr eacti
on.Thi sr eact
ioni sknownasacy lati
on.Youcan
considerthi
sr eacti
onast hereplacementofhy dr
ogenat om of–NH2
or>N–Hgr oupbyt heacy lgroup.Thepr oductsobtai
nedbyacy l
ati
on
reacti
onar eknownasami des.Ther eacti
oni scarriedouti nthe
presenceofabasest r
ongert hant heami ne,li
kepy r
idi
ne,which
remov esHClsof ormedandshi ftstheequili
bri
um tot herighthand

si
de.

Note:Theami deisalesspowerfulacti
vatinggr
oupthanthesimpleamino
group,
-NH2 si
nceresonancewithi
nt heN-acetylgroupoftheamidecompet es
withdel
ocal
izati
onoftheNl onepairi
ntot heri
ngandSter
iceff
ectsint
he
amidealsooft
enleadtoadecreaseintheamountoftheort
ho-pr
oducts.

Thegr oup–NHCOCH3 i slesspowerfulort

hoandpar adirectorbecauseof
the electron-withdrawing charact
erofoxy gen makes ni t
rogen a poor
sourceofel ectrons.Thisf acti
smadeusei npr epari
ngmonosubst it
uted
anil
ine.The–NH2gr oupi ssuchapower fulact i
vator,thatsubst i
tuti
on
occur satallav ail
ableorthoandparaposi t
ionsofani li
ne.If,howev er,
–NH2
groupi sconv ertedt o–NHCOCH3,t hemol eculebecomesl esspower ful
acti
v ator.Henceonl ymono subst i
tuti
on pr oductsar eobt ained.Finally
–NHCOCH3 i sconv ert
ed backt o –NH2 byhy drol
yzing with acid.This
techniquei sespeci al
lyused whileni t
rat
ing ani l
ineasst rong oxidizi
ng
agentdest royst hehighlyreacti
ver
ing.
PHARMACEUTI
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Aminesal
soreactwithbenzoy
lchl
ori
de(
C6H5COCl
).Thi
sreact
ioni
s
knownasbenzoy
lat
ion.

4.Ringhal ogenationofphenylamine:Whenbr ominewaterisaddedto

phenylami ne (ani
li
ne)atr oom temper at
ure,decol
ori
sation oft
he
brominewat eroccursandawhiteprecipit
ateof2,4-
6-t
ri
bromoanil
i
ne
i
sobtai ned.Thisreacti
onisusedasat estforani
li
ne.

Preparati
onofAr omaticAmi nes:
Reductionofni trocompounds:
 Nitrocompoundsar ereducedtoami nesbypassinghy drogengasin
thepr esenceoff inel
ydi v
idednickel,pall
adium orpl
atinum andalso
byr eductionwithmet al
sinacidi
cmedi um.
 Nitroalkanes can also be simil
arl
yr educed tothe correspondi
ng
alkanami nes.
 Reduct ionwithironscrapandhy drochl or
icacidispref
erredbecause
FeCl 2formedget shy dr
olysedtoreleasehy drochl
ori
caciddur i
ngthe
reaction.
PHARMACEUTI
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Thus,onl
yasmal
lamountofhy
drochl
ori
caci
disr
equi
redt
oini
ti
atet
he
react
ion.
PHARMACEUTI
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Sy
nthesi
sandSy
nthet
icusesofAr
ylDi
azoni
um Sal
ts:
TheseAry ldiazoni
um saltsareprepar
edbytreat
ingapri
maryami newi
th
NaNO2 inpr esenceofcon.HCl ;thetemper
atur
ebeing0-5°
C.( Her
ethe
temperat
ur ehast obet akencareofandi ft
hetemperat
ureexceeds5°
C,
thereact
ionwi ll
nottakeplace.
)

Gener
alReact
ion:

Mechani
sm:

Pr
imar
yaromati
caminesareusedasast
art
ingmat
eri
alf
ort
he
manuf
act
ureofazodyes.

 Azocompounds:
-compoundsbear
ingt
hefunct
ional
groupR-
N=N-
R',
i
nwhichRandR'canbeeit
herar
yloral
kyl
.
 N=Ngroupi
scall
edanazogroup
 HNNHiscall
eddii
mide
PHARMACEUTI
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 Arylazocompoundshav evi
vidcol
ors,especial
lyreds,oranges,and
yell
ows
 Ami nesr
eactwi
thsodium ni
tr
it
eornit
ri
c(II
I)acidtoform diazoni
um
salt
,whichcanundergocouplingr
eacti
ont of or
m azocompound
(col
oredcompounds)
.

Exampl
e1:

Exampl
e2:
PHARMACEUTI
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Uses:

 Azo-compoundsar ehi ghl

ycol oured,theyarewidel
yusedindy ei
ng
i
ndustries,suchas:i )Met hylor angei i
)Directbr
own138i i
i
)Sunset
yel
lowFCF
 Methylor ange-usedasaci d-basei ndi
cator
sduet ot
hedi
fferent
col
orsoft heiracidandsaltf orms
 Art
ist’
spai nts–cl ays,yell
owt oredr ange
 Dyeinfoodandt exti
lesUsesandi mpor t
antofazodye
 EXAMPLESOFAZODYESUSEDI NFOOD:
E102:Tar tr
az i
ne,E107:Yel low 2G,E110:SunsetYel l
ow,E122:
Azorubine,E123:Amar ant
h,E124:Ponceau4R,E129:Al l
uraRed&
E151: Brill
iantBlack.