References

Chapter-5
References
It9
C[.pt.r-5
REFRENCES
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N.
Appendix A
(Papers Publ;shed / Communicated)
electronic reprinl
Penlacarbonyl(N,N-dimethylbenzylamineXungslen
Tariq Mahmud, laved lqbal, Muhammail l6had, Mark R
cry{i'
o
hFirqrrldsd c+! !04r,
lrsl,rllrsnflt"l*,@
,
Elsegood and
\4'kie
metal-oirgalic paperc
Pentacarbonyl(N,Ndinelhylbenzylamine)tunSsten
el|l:dn.d n$rd,. k* r' }
rlqood rd t/Eu. acxEr
ftc ,ir! dpord, lt(c1r'',N)(corl' f, PE.'i.d
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w' t, MD'mdny'b44l irGrqdd-
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llF gdi,b rPF..dr dd{h Ltfu
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i
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in dra
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u!de! .a dF uri{ wr nd'ibcJ LY rr'IR
rE -rvd w -.r'&r r, sdlb"k
ro
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dqrd;{ b d'E tsd.dw a dd'ib.d rd d'
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or
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nu $ii,6id le{d w fud-lddre8'uf
b vFd
b kbl abr B mryMdtr' 3'vl l uEnd)
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dqi.E
onplad Cig. l) Bdhth.
r-ud.
r Flor rd e. ud lorubl' io dsorc
aE whi! '*l
l) d'r'N
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ro F
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c.l{ of dE iItI or ll! baal sP+ ft.FsE or'
bdd d l5'3 dr Cn).o ftibe b c.c thbln'l8. rh
dlddit, nlqudy orr GN tdn or$. D?. clii{
(cu)twd.t4d!d d l2t2 q- GI
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d. H-5 r.6 (dno) i, t! ddi. r & amdr
mur'iDh d d6.e€ d b. Dd..d b e F6 n
ddo ru A rakr ot!.rEd d dr'rl i du b m
;!'r r.F @M ldren ,o ddGdslh. m'c€(n
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c-mrMd, b tu $shirY sb@ Th'o P'& n
I { t..d dl t ? - d. b c2.'d c50f o" dd.
q, EtFcd$ly wHL uE FlIt d 3l lr 0 i'd 4 0r ' o
dla&db c-! 6d o5.6F4Ydt AFrrorov
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tr dEbc! A Fr.0d $ i d6 b
atnFlddl''IFo}tblyfubm.t'y|.lnv
(roll' 1) abd
dbtR|l@rof
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o e r+rdl
rh&hi'{ GcquEd ot r{ioE boilr
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5i
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lfifi n obdql dfdt rh. loc E3io al'i'n
ff'rn d! qqlGnm or oF lisbd n dD n&l
tu"!d, nirq'i rb! f&r ! '4!.n d bY h('r
,oF;!k ur ! n.{ ld ftq.n v b{d r 133 o_
-",.t.'o"r"0,"9.'b6dfmdidlYulbq
*'u.*"-,ru'*''m*,u*t'l"lu.u (,
.lcr*i,lRrsrsEvolcorm?mrbl3a3o o
rroqF t or
iD d6 nlbl .o+14 The &.ra- in
6'rYq
d
drBG
cbd,o tr b 'o @dij{
it
@bEEs
&|l
holybrflm rcn *h.h ftbilia
n L6er b B FilY co (. tri@P6 4r'd).
L'N|Lt['ll!dlhlftbl|b.$dor.@
si&hr ido cldrd dclr 'rl rM lR rft@4
idrqd'trn]4iTlrk'r4o.v(@lddrrd!
i!;dYrNnxorqrbrs45r*)m_ssedtub'
r."i a* a.u* *.-,v t- v o w
'
fndb.crdoEloluP?d|tn!lrlilFdoNl!
&DNLynoglmfid2'b.qo.DMRAuqn6
x@d'&rddn TIE drd'l nrad' .ryuds-u
"r-."'c.".tuy't",PF",,*"to"uo",qnr6'ruJdrbv(MN)
fl. ! Nl'a .Fh
!u'uhlhq'alrnLFM{r(llonPb (I$k trw
dFndabH r''Nt'dd
ns
b Hr !'d c I'aB & o@
.tri d.F
Ilffu'mmd!Ifdddsb|I.4Ndry|@Fln
'|d|.$*lcjdr'4dl[N{d'|Fer|ll', i(r,,i; d a716
ir.":',".il
::"lHffi ilS"l,:ilH:itr;
..wt.u*"a..'t'yt.*t'""'mp*..
, e;i'd-'rn".ruo'i$a'd H"*d"dYs*
p"' ptu' to q
,r'n.r.qar rd Elb ForG
,,L.ro r" rcrFl'l $a ofo
@
rd
o
r 3
lpm ra
htrtl
nJuddbE@cd'lbdd@*'!fu4cI4
A
'r".,,r.|d 'h,r\
"r.l't 0 3 I'i"" o "*
^d"i
'tuldrd@d@ilds!{rxldsndllfl
oFD torFrr !i@ Thul r6ldftn bndrl
*di,t*pt-'uocw'au'""Y'*
qib 40 Fn huutb
tbrltwdfr'n'drjh4[d.63I!ql|i5wo'
dqr
a rA d .tdr dllo. r9l :02 tu Lv'
"r
-T,""rii.'frif:;*
H:ilri*'l:"iHrllK'lii]:
cmlod'aloll.r'im,jlplddd.?,5
ffi:,rlri,t.F*'rtr'
rt"-F-"'
I
l* 'b"
"
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z6a
*m;rtx"-;:#ffi;m.*
:tr"T,#Til'ffi"'fr*iH'ffiT
xi.sffi $u*Js'H,r"rlqi i;
lf#'ffiliffiffi",#
mlg:m;""r#"ll'mr:;t
ffirta5;ilHTlf;:-tr','J
l@@ rlh unslo urqh ddd'
'xrq
^CK^O\IAEDCMENI
,"#"ffiff.*'lTfrs;tt#';ji
i:"ffi"ffi#**#-d*;u;
oI
r..( s..r.1,2m4. sdi-i. od clrtdidim drl!
Ndud [d dioo of\,loLt clnd'YL Pl (co,
iM c'. Mo. w). tu (co), Br, M! (co), cpl vid,
l,q'zylanierevitibd.Pdylato'r?2 23r 291.
M,is, c , s/, 2lI)1 oid!'ql hiBry oryn'l rn
n.r}t.rridioo dqlilEnic Pd (tl) @{t!G in
. ls&lu! rgi"E bdv€' iMlFr ui l,liilirt
Drld'To'r., lo 13521351
r{ut, lt 14 dcr.l99. nH'ddss'irtmFrh
or,v. i'|Di"dlvlsEyr&Di'E d'dG ri'h rlvd
0), sd,r (uu zid (IIl sdnim oDdd mefr ([)
t. A'sl AppliqlPyrcl, 52: 119-l50
hQlrzd. risr.d rmtu r,!.l6o,2e ]|_3'a
r-jq, M .! ql. ?00t. rdEttdt{4 r.
Dhurhylbaldtr) trr@ Ad GYtun.s.,
YmaS.O,ral.,20O:S9..Mhd elin.tis{idd
a[,on,
J,,t,
2co3
rlr cyohil.(|donEdioo
as,lr,o/,r.,/r.firldimmii!.d'dNb'lRddn
ti|ic!i|PPoeddd'tdlydNw'I'q!n.'
r-i!*nc rq!240.] q,rlsi.n x.trr rtu d
qnn'it
liaid. L ollddn
sn Nrl encrb qd6
dpr'Ellanwn2diE
h,iq K. r,i, 2md Thmmlti!.! iMradtm of
ljtuis (vI) &d duiM (IV) .mpLxd. Rdio
&licyldd.td! I\,LuuHlroylb^+rzm,
cad chd. 5?: 13'133
Tir, L.F. a .r, ,04. stnosL or dirule sdrp
6 idd €nc/ tnPldc rtidsd bt .{ a.
p.n@boryl (!rdzi$) n.d (0) cmdds of
sdrp 6ddd. z. N.&fo@\ s?L 9! 93
!||trdtt*oa
d{2..tloroi.BD&4}r!.tu b.old.
Ar
v
tura*r.*rrrrl*athr.IEa.}dllaH'F
trn . .a (bbv, Ihlilt o, lb lu|., r&' tljtollnPi-'
3IU'
rody DFl4 trabcrt tb[{', k alql rd.
c6.r&.dl$arf
(B.hgsbi!.db,,LaCr-&|'lfels'cidB)
.
By the etion of h*adecyl halid. on hel.rocyctes seh
6
Prtidinei for
dmple m.ilyb.rld€ylPridinim bsnidct2l
.
By ihe
.
.$eB of Fdimelh/dino b€mic &id[]1.
By lhe eelon ofs conpoud hlving a leftiMl .poxy gtoup viih t rli.ry
&im
&lior of I'haloalkdes ed alied
followed by dE .ddilion
compoqnds on th€
hiels
alkvl
ord &id[4]
.
By ihe @tion of a teniaty
di!e, d
.
coryoud giving qut€h!ry amonim conpomdt5l
By lhe rcedon of d au(yl halidc wiih ptridire or inid@I. at
alkylahng agen(
ald
&
.poxv
l2O0C (o
35ooc16l.
.
dins, mc|hml ald a cyclic Ble{71
The appticltions of qual€n..) lmodiM coDpouds e.xtenelv wid. ranging in
difr@ fields. Th.y @ g€ffilly su.d d antisltic tgen! disitrIdt4! invcd sP
sdirizo in debrScitl8l. pr€sru.liv€. active gndie lor condidon$ lntistalic
By the
twhor
of teniary
.genl, soIiGM for l€xtilA
4d paps producs, w@d prcsdativ.,
emuNrying
agqr
disFrsd, lub.icmt, slani.8 marcrial for ncdicines, P€sticidcs' ionic liquid
in.leu@lFmical prl)(xs, brishtqs in clarropltline" cle$ tehmloev' (@val
pignenl
ol pollutant) ed as phdetrnnsfer et lysls.
syMgjsric qtretion of met ls.
These
@
also vetv usetul for the
us of thse compounds d biocides in wd prc*Natile, paint &d
liq@E is inc@ins dpidly. Qulq.'ry amonim @nPodds hlw b€en
enthusi$tically utilidd for vdious Poltmd lpplicatio.s i.cludilg honoid
sJarh€b, polld.riz,tion, ituluding @trdlneiolr aionic ad fie adi€l' and
Tbe
pollhei modrfi€tion by polymd ch€nisK
[91
dL , I o nnole ) {as dissolled in 25 nL
nL of t .thvlmirc h ldded' folloeed bv th€
2{hlorobenzyl bonide ( 0.65
dichloomdtr4 aod th€n one
of a solutio! of 33% dinclhylmine (0 20 n[ l 5 m.@le ) in €thmol was
add.d dreFwi* to the Eacii@ binw ed nired fd eight how in a quick_lll
Il6k.It ss thd n€ulrali&d wilh loolo sd@ bicebomt€ solution. The mixorc M
.gain $i.ed od orgmic lay€r *s *p.dlql, dried ow lrhvdrcs nagnesiun
addition
B
coMnlr.t d on . rclsry €vaponloi, It s6
th.n c.olcd in Eliigmro! b ga the pw pDdud .$ @ldl6s ne.dlc litc cqslsls.
sulfat€. filler€d off and rh.
The yield
ellenr
wa about 4l%.
moniun bremide @ holabd
in p@ fom and ch@tcri&d by difrdit sFcoosic t4hriqEs, i.q IR,NMR
Thc conpomd di(2-chloobsuyl)dincilyl
IR:
TrbrFr: IR slr.l.titrg
fr.qlldi*
of
bl{2r
(-cE
c-H
3053
2861
G)
(m)
Thc srucruE of ftc qu|.maly
)
c-N
c-cl
t5l
n6
I
mBonim ws .st
spcrroscopic d4a. The absoryrioi peaks
b.i4
osbenzyl) di@thyla|rmniM
c-c
1600
blished on rhe b6is of IR
ofvsion! vibdtioN
in the conpound were
nt€ absrltion bsd ar l053cmic) M assigftd to C_H siteiching of the
dng \tilc tlE pel.t 285lhn(m) @'Esponds to C-H ofn thvld. ofih.
b.nzyl 8roup. Simildly rh. pr€sne ofabsorplion bmds at l60ocni(n) ed ?76cnad C4l srrebbjrs Bperivdv The chret€nstic
\n) tuy b. Nigned to
C{
teqMcy
of a C-N bond of the
O!. CHr-N(CHr, \ta! obsw.d at I lslcDi(n)
lboolplior bandr in tlc ESid 69G5t5cEr(n)
dd N-H vibralio$
respectively ofthe
ofrh€ roducq indionig $al both lhe
ad 340c3250cn'r(d)
siding @edal, de absol in
Eetltll
Tbe
due to c_Br
the IR
sFcllm
hav€ heen cotrv.rted inro the
dcstld
NMR:
T.bb2: NMR spelll
.H-
dlta of bi5(2ahlocb.nzyl)dimedylumoniuo bromide
Itc- NMR
NMR
N,CHr
2l5k)
N-CHr
45_54
4H:
{H2
6t.10
H.l
3.45(5)
7.34(d)
c-l
140.02
H-4
7.10(m)
c-.2
c-l
c4
D6.40
1t4.30
t24.20
c-6
127.10
110.40
HJ
H{
Ii
1.12 (d)
the preton
NM&
tb€ p.ak at 6 3.26 (ppn)
cotBponds to two
{til
sreups
ath.h.d !o a quandaary Nirrcscn.'I1,e pdr at 6 5.38 (!ph) @ftsPonds to fou
beuylic pbtoG
ti.
sidc md on
beaw
t
wbon
the
viciniry of
b.tw6 6 ?.48 -
e
aryl eroup *hicb caued a hieh
?.56 (ppm)
(rftslond to six NDali€
ptlst@ of thE Pblo6 on @bon alotu 1.4,5 @
while the peat at 6 8.16 (ppm) co be aiiribured lo two potons
prcb.bty
bo$ domalic dnss
anached ro
..c di@tly atlached lo +vely chdged lr'dom on oE
otha side it ey @ in
The nultipl.r
poronr,ll
they
du
arom 6
to lhe
i.
bolh
enalic
rirys.
Duing rhe diMiion of 2{blorb.nzylbronidc, uusual cr}sials fomed which
wse ielaled. ln ord4 to esrablbh th. structe oI thes. crystab, ihev w€e
alrlysiz.d by single cryskl XRD ie.hniqE.
cry$ak
@ of
bc(2<hlocbetzyDdi@thyl
Ii w obsflcd thal ihet ielated
amonim bomide. a qut m.ry
, TlE XRD par&Elcs includine bond len€lhi boid dgLs dd
ietropic d EU as &isropi. displencDt plmct rs wF int€Ipl.i.d which @
a@onim
sla
@[.di@: Sr44ir Grub, 198! ccl r!ftdot ${.a T (Bn*q, 198)r dtt
Ed&1id: vnlrl: p6ognD(t) u!.rl lo soll/! .lEor!: .51iit4l'7l (Sb.Llrid.. 2001I
procnh(!) u!€d ro |lfrc ttructuE: SHEIXILi tmllfrn{ 8nPhi6: SltEzrli
Dala
roi*4 sd
ro
F4G orLtil
fo.
F$li.aioo
SIIETXTL
nd h.d
F.8rbr
Q*n
rL-l
Siqb dyr.l x{ry 4.(t'm of bid2{ibo-hdzyl)din ltyl
.'!@iE
o
nF2.
Amlb via of tit'gle qFd t{tt rpcdu of
b.@ylldiDctn 'l dDoiu hmid.
6
Ud2{hlol!-
F
S-!.
clos psking x-6y
of
bis(2-chlocb€nryl)dim€rhyl
CrFtrl drtr rod dctur.
refireD.nt
boDrde
bdzyl)do.rhyL@olird
C6HTBICITN
J75.t2
150(2)K
C.rslat syst m,
slse gooP
a=11.9427(5)A
b= 8.9771(4) A
c = 15.0759(6)-A
9=97.41r(2f
1602.80(12)4',
z
2.EE8mj
760
F(000)
coloulds,0.E2
R.fl€.tios for @ll
EfircfBt
r&g.
for data
CmpLt
re
colle.tio.
to0=26.00p
O.t6 x 0.32
imr
(0tuse2.33ro28.71')
8351
Bnrtcr SMART 1000 CCD
o etatio. wi$
0
t
2.05
nmw fi"des
$2a.n'
h-151015,[-ll
to l
l,l
19 !o
v
t3470
3816(Rh=0.0145)
3462
*mi-dpind
Mir &d ma. Famision
frcm cquival4ts
0.201 and 0.458
di!€cl netho&
Full-nairix l.st.squdes o. F'
Weiehti4 pamelea 4 b
Dr, / NE8inls / pqrancld
0.0215,0.7575
38t6/ 0/ 183
Rl = 0.019, wR2 = 0.0461
R I = 0.021 l, wR2 = 0.0474
1.025
L{sesr dd mee shiwsu
Laqe$ difl. p€al dd hol.
0.385
ild
0.209 e
A
r
20
Atodc.oodi!.tec ud.quivrL.t boircpi. dbPl.cenenl p'nh.l'r3
(F) for blt{2-clloEb.lzyl)di6.Ovl.Eno ud bromid€ Ua ir
;.fberl .t o!. dlird of th. ltft. of rlE o.thotodlial U' t'!mi
ql?
-0.10616(12)
T.blFs: Bond Llgth! l^l Dd .!g16 lol ror b!(2{tloGbttzyldiDdhyl
.nnoniln hmDide
q2lc(r)
r.3r3Q)
c(7fN(r)
r.534(r6)
N0fc(9)
c(r?lcr(2)
rira(2)
c(2fa( r){(6)
c(6!c( r)-c(7)
qrl4(2)-c(D
qllq2)-c(D
c(2)-c(38(4)
cal.{4)-c(31
C(9FNOF(10)
qsfN(rlc(7)
qrrlqro)
c(
ll1.24(r0)
c(ets{ofc{7)
l|0.3r(r0)
N0)
co3}{( l1}{(
l4F(r 3)-c02)
t0
r5)
rre.9J(r4)
Alit.repn did&6.n1 p.nd...B (45 for bu(2dlon'
b.rryl)din.tlylmrolirD bt nlii4 IL uirotnpic dltPLeD.
ftcror dDoo.nr
..kd
rb.
fod: -2lD:. rUrr
utt
ll
Uts
+ ...+
2hlt!'b'U':1.
UB
UD
r.rb?r
Aydi.sr oqdi..tr .!d aoa[pi.
rot
dLtlr@t Fru.&r| (f)
|t{t _Lrqta.5iFb,I!i-@5n
b|uida
BG)0.5336
l(r)0,3957
l(6pr?ra
H(7 )
H(7a)
r(rB)
0.t2t1
0_1322
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ACKNOWLEDGEMENTI
Th. adno6 tbant tbc Udvdily of l[ Pujah t hoE, Pal$tan, dd rh.
cheles Wall@ Patislln Trust fo. fimial $ppon. $d N tle 8!.1€tu1 to
D@arttned
of
Ch€mistly. Louehboreugh Univdsily. Lrughboough, UK, idr
ptuviding Fs.@h
facihi*.
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