phrrong phrip srl dung chdt itc che dang duoc rlng dung mdt c6ch rdng r6i do vi6c srl dung thuAn loi vi d6 ddng hdn so v6i c6c phtiong phAp khdc.. Trong bAo c6o ndy chring tdi trinh bdy
Trang 1,
/ , 1 T
jl TlCl{ rr^
-j
'rgr{is$c$
r$sN -0868 -3224
T r g
4
2004
Trang 2Tap cht Ph6.n tr,ch H6a, Ly ud Sinh hoc - Td.p g, s6'4 - 2004
NGHTEN CUU SU TUONG QIJAN GITA CAU TRUC OIFr.r rfi
VA KHA ruAruc Uc cHE.Aru ruoN c&a oAy pAru xunr PYRIDIN
D€n tba soan 31 - 5 - 2004
Pharn Vin Nhi6u, Vfr Phddng Li6n Trxdng Dai hoc Khoa hqc TV nhi|n
Vfr Hirng Sinh ViAn Hoa hoc cong nghiep
SUM}IARY
STUDY THE CORREI,ATION BETWEEN ELETRONiC STRUCTURE AI{D
INHIBITOR EFFICIENCY OF PYRIDINE DERTVATIVES
Using inhibitors to preuent metals from corrosion is a simple and uery effectiue way Howeuer, the effectiue inhibitor for each kin,d of materials and certain enuironment must
be found The research on the relation betueen electron structure and corcosion (inhibited,) inhibition possibility on the basis of semi-quantum calculation method combined with multiple regression, allows us to predict, eL'en find the best anti-corrosion inhibitors and, mahe further plans for practical use and intlustries
nrd oAu
Sr: en mdn kim loai ldm thi6t hai ldn
cho n6'n kinh td qu6t dAn Nghidn ciru, tim
c6c giAi ph6p ch6ng An mdn, bAo vO kim
loai ld nhi6m vg c{p b6ch dat ra cho c5.c
nhd khoa hoc Trong s6 c6c phrrong ph6p
bio vQ kim loai phrrong phrip srl dung chdt
itc che dang duoc rlng dung mdt c6ch rdng
r6i do vi6c srl dung thuAn loi vi d6 ddng
hdn so v6i c6c phtiong phAp khdc Vdn dd
dat ra li cdn phii tim duoc chdt irc chd c6
hieu quA nhat cho hlng loai vAt li6u vd
o A
rrong trlng m6i tnrong cq thd Dd girim b6t kh5 khdn vd t6n k6m vd kinh rd cho c6c rhi nghiOm tdng hop chdt rrc ch€' cAn c6 nhr3ng tinh toAn lj thuydt tnJdc Od iam co s& cho vi6c dinh hu6ng t6'ng hop c6c chdt c6 khi ning rlc chd an mdn t6t nhdt
Trong bAo c6o ndy chring tdi trinh bdy kdt quA nghiOn ctu mdi quan h6 girla cau trric diOn trl cria c6.c chat r1c chd v6i hi6u suat rlc chd an mdn cria chring [1, 4, 5] bang phuong phAp tinh to6n b6n h-tong tr3
va hdi qu,v da bidn
Trang 3Bao cdo gdm: nlng ldm chdt rrc chd an mdn tol, thrrbng
, drra vdo 3 ti6u chi sau:
llghr0n cUu mor quan ne g"iua cau truc
dien trl v6i khi nang r1c chd an mdn Fe - Chdt d6 phii on clinh (bdn) trong didu trong mdi trddng HrS cua pyridin vd ki6n lim ric chd
dAn xudt melyl pyridin 3 cdLc vi tri - Tao mb.ng bam chat rr6n bd mdt vat khAc nhau bing phtiong phdp OU:
"d., U"o uC lrtong tt kdt hop v6i phrrong ph6p hr)i
Drr do6n khi n6ng r1c chd dn mdn cua C6c ydu to tr6n c6 srl li0n h9 chat chd c6c dAn xuat kh5.c cua pyridin v6i c6c thdng sd c{u tnic di6n tr} cria phAn
t r r P h A n m d m H y p e r C h e m ? 0 l a P h d n
PHIJONG PHAP NGHIEN CUU
P5rridin vd c6c dan xudt ciia pyridin Ih
nhting chat c6 kha nang ric chd An mdn
Ket quA thttc nghiOm da minh chrrng die'u
d6 Ngudi ta do khA ndng rrc chd h.n mi)n
(R"o"" - t6'c dd dn mon g/m2h) Fe cria pyridin
vd c6c ddn xu{t cria pyridin trong mdi
trudng dung dich HrS bdng phtiong ph6p
trong luong vdi c5.c mAu th6P :20
( d = 2 0 m m ) b d d e i ' b = 1 5 m m i n d n g d d c h { t
r1c chd: 5 x 10-3g-mol/l; HrS: 3.0mg/1 [a].
Khi ning r1c chd in mdn cria m6t chdt
phu thu6c vho thhnh phdn h6a hoc, cr{u
truc phAn tt DC d6nh gi6 mdt char- c6 ktii
mdm ding dd thiet ke phAn tli t6i rJu h6a hinh hoc vd tinh c6c ihdng sd luong tr.t cua phAn tu rat ti6n loi, d6 sii dung va cho ker qua d6ng tin cAy [8]
1- Trudc hdt cdn khAo s6t lua chon phrrong ph6p tO'i rlu h6a hinh hgc vh phrrong ph6p tinh phi hop cho pyridin vi c6c clAn xuat cua pyridin Chung tdi de toi riu h6a hinh hoc vd tinh cAc thong so iuong trl crla phAn trr p5'ridin bang tat ci' cac phrrong ph6p b6n h:ong tri c6 trong phfin mdm HyperChem 7.0 M6t so kdt quA thu duoc dem so sAnh v6i sd ii6u thr:c nghidm [71 'iuou iiria ra t,rong c6c bAng I vd 2'
Bd.ng 7 Cdc g6c liAn hA|
Phuong ph6p < c 6 N C 2 <NC2Ca <NCzHro <c2c3c.' < C a C r C , <crcrHu
AM1 L17.231 r23.504 1 1 5 7 0 8 1 1 8 4 3 1 1 1 8 9 0 0 121 162 Plv{3 l 1 v D / r - 1 2 1 5 1 6 I l D / / / 1 1 9 0 5 6 1 1 9 2 8 3 t 2 0 6 9 2
Z I N D O 1 1 1 n O t r ' 7 1 2 3 5 3 8 1 1 4 5 6 9 1 1 7 9 6 9 719.729 1 2 1 3 3 3 Ii6ut7l 1 1 6 8 123.9 115.9 1 1 8 5 ,I -TiJ.J 1 2 1 3
Bd.ng 2 DO d.di tiAn hA? ud m\men ltong c@ (D) Phrrong phSp N - \ , e C - C u U a - r r l l C r - C , C r - H t C , -H t o L)
AM1 L 3 4 7 4 1 3 9 6 1 0 9 ' , i 4 1 4 0 7 1 L 7 0 4 7 1 0 9 9 5 1 9 7 4 PM3 1 3 5 2 9 r 3 9 1 r 0 9 4 3 1 3 9 5 4 1 n o i o 1 0 9 4 8 I Y , J O
Z I N D O 1 1 3 5 0 1 1 3 9 3 r 0 9 4 2 1 3 9 0 5 1 0 9 7 9 1 0 9 6 5 2.387
I ? I
L i l
Tdi Ii€u 1 3 4 0 1 3 9 4 1 0 8 1 1.395 1 0 8 4 1 0 7 7 2 2 1 5
Trang 4Tir c6c sd liOu & bAng 1 vd 2 ta nhAn 2 Sr1 dung phrrong phAp ZINDO1 dd toi thdy tdi rru h6a hinh hoc bang phr:ong r:u h6a hinh hoc vi phrtong phip AM1 dd ph6p ZINDO1 vd tinh c6c thdng sd bing tinh c6c th6ng sd h6a lrrong tri cia ddy phrrong ph6p AM1 cho kdt quA tdt nhdt pyridin thd Kdt qui thu Cr.toc cho 6 cilc (phn hop v6i thdc nghi6m) bAng 3,'4
i1,r- -cos.-*rr,\
/-\r-at3l\ nr(.-\r.CH, r,\
H:\r\
t i t - i l | t t i l t i l t i l t i l l
(r) o F) (4) (, (6) HiC (7)
C6ng thtlc cd.u tao cia pyr;idin ud ctic dd,n xudt cia pyridin
3 C6c rh6ng h6a luong tit tinh drroc, kdt hop v6i c6c gi6'td R}, thrlc nghi6m [4] duoc dua vio phdn mdm xrl li so 1i6u vd quy hoach h6a thrrc nghiOm STATGRAPiCS 6.0 dd hdi qui da
bidn [e].
Ndt quA vA rHAo LUAN
Hinh I Ctic d.q.ng bidu d.i\n ph6.n tt 2,4,6- trimetylpyridin sau hhi da t6i ttu hoa hinh hoc:
(a: d'ang nJdng, b: dang ciiu, c: dang phdn b6'di€n tich) Bd.ng 3 Cd'c gid tri ndng ltong cia 7 phd'n tt tran
'.1 ' /
H
H , , - ' H
rY
l
- , ' C : , / H
- *.'r,' -.a'-'5'
: i l i
l \ , / i
./).r-_-' -/
.2.'Dr.-, ' v-'
\//
-\.- r H
N ; C H
!
it
PhAn trj ! b b l
n
I - 21107.937 - 1 1 9 5 5 0 2 - / / l-vo.ouo - 1 9 9 1 2 4 3 5 r 9 7 9 0.388
2 -2470r.907 - L 4 7 7 7 2 7 .i00788.660 23224.ri9 2 1 0 6 0 3 0 8
d -24699.453 ' 1 A n R o n Q
L a I u , L I O 100946.732 -23224.r79 r 7 1 7 0 3 0 4
^ -28295.84r L I D Y Y ) I - 1 2 6 4 8 9 6 1 9 26535.923 2.239 4 2 7 8
-28290.720 - L 7 5 4 7 9 6 - 1 2 6 9 1 3 9 2 1 -26535.923 1 4 0 0 0 2 5 0
o -28293.542 -1757.618 - 1 2 6 3 3 8 0 9 5 - 2 6 5 3 5 9 2 3 I I V I 0 1 9 4
7 , 3 1 8 8 4 8 7 1 -2037.203 -154730.257 -29847.667 1 7 7 9 0 2 1 0
2 6
Trang 5PhAn trl Eru'o E"on,o S(A') V(A) Ii
1 0 1 8 3 - 1 0 0 4 1 9 7 6 3 9 3 1 7 5 7 3 - 3 , I 1 7 l b b b 2 3 8 3 8 9 7 2 5 - 0 2 0 3
z 0 i 5 6 - 9 7 2 5 2 3 5 4 0 5'368.786 - 2 5 1 0 2 1 " 3 2 2 8 8 7 9 r 1 5 6 0 -'0 i'gs
0 r 8 r - v i , t D 234.286 3 7 r 2 9 2 -2.233 1 8 4 9 28.769 1 1 5 6 0 -o.242
4 0 1 6 5 , 9 5 2 5 2 7 2 r 3 94 2 1 5 0 8 r 2 1 6 2 5 9 9 3 3 9 2 1 1 3 3 9 5 0 1 8 7
0 2 0 8 - 9 4 6 4 269.255 425.186 -0.745 o n l 4 a ? ? n n 1 Q E O R - 0 2 8 0
o 0 1 5 2 9 4 3 5 273.197423.888 -0.924 2 3 i 6 3 3 8 1 0 1 Q ? O i 0 - 2 3 5
7 0 2 7 9 -9.412 3 0 5 2 3 8A ' 7 1 ' 1 2 0 4 0 0 2 5 0 1 38.742 1 5 2 3 0 -0.293
Et,,t,,t: Nd.ng ltgng t(ing phdn tt
(kcal lmol)
En: Ndng ltong liAn hAt &cal lmol)
E,: Nd.ng ltong electron (kcal lmol)
8,,! Nd.ng lxqng nguy1n tx (kcal lmol)
Ercv6 Ndng ltgng obitan phd,n ti trong
Iop thdp (kcal lmol)
Euovr,,: Ndng luong obitan phd.n tt diiy Ifu
cao (kcal lmol)
Pyridin chi:a c6 nh6m the c6 t6'c d6 irr
mon bang 0.388 g/m2h, s6 grAm xu6'ng
0.304 g/m'h; 0.250glm2h (tfc 1dm tdng hi6u
suat rirc chd tii 70% Idn 76%; 87%) tudn€t
rlng vdi c6c chdt 2-metyl pyridin;
2,6-dimetyl pyridin TOc d0 an mdn cdng nh6
trlc id hiQu dudt trc chd An mdn cirng cao
' I ' o c d 0
A n m o n g i d m c i r n g v 6 i Z y Z y 1
giAm trr -0.203 xudng , 0.280 s6 ihm giirn
tdc dO dn mdn tr] 0.388g/m'h xudng
0.250g1m2h hay t6ng srt fc chd trl 7A% l6n
8 7 o / o
Srl dung phAn mdm STATGRAPHICS
6.0 igl dd thuc hiQn ph6p hdi qui, tim m6'i
quan h6 gita l6c do dn mdn hay hi6u ndng
bAo v6 (R"o".) vdi cAc th6ng sd h6a luong tr:
Bdng 4 Cd.c thbng s6'ltong tt
T
L H ,
logP;
P ,
4 L , , LN!
Momen ltdng cuc
DiAn fich bd mdt phd.n tJ (A') Thd tich phan ilx @3)
Ndng luong hydrat hoa (kcal lmol) log hQ s6'phd.n b6'
Khd ndng phd.n ctc (A3) Chi s6'khuc xq (Ar) Mfi dA di6n ttch tr€n nguyAn fiJ N
(ndng ltlgng E, d0 phAn cuc D, c6c ydu t6' hinh hoc, ZN diQn tfch trdn nguydn trl nito, ) cria c6c chdt rrc chd da cir:oc tfnh to5.n 3 tren Phtrdng trinh bidu thi mo'i quan hO d6 c6 d4ng
R"o = const + la,x, a1: hO sd cria phrrong trinh hdi qui
*,' ie ydu td(E, D, S, V, ) i = t "5
Trong thong kO ngridi ta thttdng d,:a uao g"ie tri cria he s6' tlidng quan R2[9] (correlation coeffient-squared) Gi6 tri cria dai lrtong nhy thu ditoc cirng vdt const vb' cil.c a, trong phrtong lrinh tr6n khi tfnh theo c6c yeu to
Trong d6:
Trang 6A Tdb dQ an mdn phu thu6c uao ,7 yd,uj?', S
R.o,, = Rr = 0.713454 0.001713*S
-Vdi R! = 0.8061
O TOA dQ dn mbn phu thu6c ud,o 2 y€u t6': S,
Eruro
R.o" = R2 = 0.705581 - 0.001941*S
+ O,B4E444E"uro
V d i R ' z = 0 8 1 6 4
g T6c dQ dn mbn phu th.u6c ud,o S yeu t6': S,
Er,n o, Z*
R"o, = Rs = 0.?3?943 - 0.001?13*5 +
0.843707*Er,b'o + 0.7888gg*Zu
Vdi R? = 0.9120
O T6:c dQ d.n mdn phu thu6c ud,o 4 yei to': S,
Errro, Zr, Eron,o
R"o"" = Re = 8.902372 - 0.006389*5 +
2.586596*E"uno + 2.112425*ZN +
0.726993* Ello*,u
Vdi R'? = 0.9740
8 T6:c d6 d,n mbn phu thu6c ud,o S y6u t6': 5,.
Etuuo, Z7{, EHsy6, G
R"o, = Rs = -0.6M7 - 0.O03595*5 + 2.019082*Eru*c,'l,+ 2.561361x2,* -+ 0.247777* Eno"o + 0.03?546xG
Vdi R2 = 0.98b7
@ T6:c dQ dn mbn ph.u tnu6c uarc E yeu t6': S,
zu, G, Eroro, E, R"o = R's = - 3.245825- 0.02166?xS + 1.312767*2* + O.023372*G - 0.2109* Enoro - 0.002799*EB
Vdi R'? = 0.981b
A T6A dQ dn mbn phu thu6c ud.o 5 yA'u fi': S,
ZN, Eruro, Eroro, E, R"o, = R", = 4.602395 - 0.01073.3*5 + 2.63237*^1 * 1.61BI5*ELU-9 + 0.0941828 Enonro + 0.282g28*En
R 2 = 0.9788
Bdng 5 So sdnh gid tri R",,"th4tc nghi|m rd R),,,, h6i qui
M A u R"o."TN
Ri.,,,,Htii qui (g lmrh)
p
r L o r L 3 R D
I L
5 R " ,
1 0 3 8 8 0 3 7 4 8 0 0 3 8 5 7 7 n a o e A o 0 3 8 5 2 4 0.38982 0.39020 0.38404
L 0 3 0 8 0 3 1 0 0 9 0 3 0 3 0 6 0 3 1 2 5 4 0.32003 0.31067 0.31081 0.31360
0 3 0 4 0 3 1 2 0 9 0 3 1 4 0 50 2 9 8 5 6 0 3 0 0 1 50.29768 0 2 9 6 7 7 0.30822
i 0 2 7 8 0 2 4 7 1 5 0.23490 0 2 6 3 5 3 0.27093 0.27602 0 2 7 5 7 5 0.27516
0 2 5 A 0.25209 0.25549 0 2 3 1 3 8 0.24847 A q R > E t 0.2528r 4.24612
o 0 1 9 4 0 2 4 5 3 4 0 2 2 8 3 3 0.21289 0 1 9 4 6 1 0.19527 0 1 9 5 6 9 0 1 9 3 0 3
R2 0 8 0 6 1 0 8 1 6 4 0 9 1 7 0 0.9740 0.9857 0 9 8 1 5 0 9 7 8 8
Bing b cho th{y 916 tri R2 teng ti le v6i sd
ydu to tham gia vdo phrrong trinh hdi qui
didu d6 c6 nghia ld sq phr) hop cua phuong
2 B
trinh hdi qui phr; thudc rat nhidu vAo so ydu
to sd ydu td cdng tdng phutong trinh m6 ti cdng phr) hop v6i thrrc nghiOm (l-rinh 2)
Trang 7y = 0.0517x+ ().7441t
Rr = 11.9237
- a
.Sii rcu tii
1 1
, E I
L
Y 0 e
E
a-.3 o.e
0 7
Hinh 2 S( phV thu6c cia R2 udo so'y€u t6'
trong phttdng trinh h6i qui
Od aann gi6 mirc d6 tr:ong quan vd d6
chinh x6c cria phrrong trinh hdi qui, ta so
s6nh cac 916 tri t6'c d6 dn mdn tinh theo
phrrong trinh hdi qui (R,,,.,.) vdi cdc t6c d6
an mdn drtoc xAc dirih bing thr]c nghidm (R::,) Bhng cdch thay 916 tri cAc rh6ng so h6a lrrgng tr] vao c6c phrrong trinh hdi qui,
ta thu dr:oc c6c gi6 tri tdc dd an mdn ly thuydi (R:,,,,) Bidu di6n srJ tddng quan girla R"o"" v6i R-,, thinh 3), tr) hinh 3 ta nh4n thdy.gifia hai dai luong R",- vD R],,,, c6 m6'i trrdng quan rdt chet cho v6i nhau (ddu c6 R2>0.95) vd phtrong trinh hdi qui bidu di6n sq phq thu6c gifla R""* vdo c6c tham so h6a ir-rong trl cdng chfnh xac khi sd y'du to cdng nhidu (Dd tin cAy cria phrrong trinh hdi qui ti 16 thuAn vdi sd ydu td rrong phuong trinh h6i qui)
0 4
s 0.3 i6
T
, 3 o z
3
(' 0.3
:tr
) { a a
d a
0 4
U J
n {
R'=0,9976R+0,0007
* = 0,9976
R " , , t h u c n g h r 0 r n
( B )
Hinh 3 n6 thi bidu di€n m6i txong quan
gitra Rt:!,, - R),,,, (A): 3 y€u t6'; (B): 4 y|u t6'; (C): 5 y1u td
Srl dung c6c phrrong ph6p tfnh toen h6a iuong tt de lr-ta chon dd tinh cAc th6ng sd h6a h.rong trl cho c6c dAn xudt etyl vd nitro cria pyridin, kdt hop vdi phr:ong trinh hdi qui cri.a R" " phq thudc vdo 5 ydu td dtj tinh
du do6n t6'c dO dn mdn cria cSrc dAn xudt etyl vd nitro cria pyridin K61 quA thu diroc cho 6 bing 6
(A)
rc)
R * = 0 9 5 8 5 R + 0 0 ' 1 1 5
K = U 9 5 d 5
a
Rcorrth\tc nghi6m
R * = 0 9 9 1 3 R + 0 0 0 2 4 R2 = 0.9913
30
'4O
Trang 8Bdng 6 T6:c d6 d,n mbn irrt dodn cir:, m6t s6'd,6n xud't etyr ud, nitro cia pyrid,in
dxdc tinh qua phtong trtnh h6i qui @ ua @
Sri dilng phtrong ph6p ngoai suy d6nh
gi6 khi nAng ric che an mdn cria c6c dAn
xudt p1'ridin v6i c6c nh6m thd nucleophin
(-CrH, vd -NOJ 3 cac vi trf rhe khac nhau
cho- th{y 4-etyl pyridin vd 3-nitropyridin cir
khi nAng l1c chd An rndn t6t nh{t so v6i cdc:
dAn xuat khac cing ioai nhrrng vi trf nh5m
rl-re kh6c nhau
Nfl luAN
i Da tim dr:oc m6i quan h6 girta t6c d6
an mdn v6i cac thong so cau tnic tii6n trl
cua day hop chdt thd crj.a pyridin bdng
phr.rong ph6p rinh to6n b6n ldone t& kei
hop vdi phAn cich hdi qui tuydn-ttnh da
bien C5:c phrrong trinh hdi qui ddu d6ne
t i n c a 1 ' ( d d u c 6 R 2 > 0 g )
.2 .Gia cri crja he s6'tucrng quan (R) vA
sd ydu td trong phr_iong trinh h6i,qui tf lQ
thu4n vdi nhau (hirh A, B), trlc ld'ph6p-hdi
qui cdng chinh xdc hon khi s6'ydu tdtdng
3 Phr:ong ph6p kdt hop gita vi6c tinh
to6n h6a h"iong trl vdi hdi qui da bidn dd
khio s6t srr ii6n h6 dinh luong gllta cdu
tric - hhd ndng itc che rin mdn cria m6t ddy
c6c hop chdt hrlu co, c6 thd cho ph6p tim
dttoc c6c chat c6 khi nang rlc chd dn mdn
tdt hon bdng c5.ch ngoqi suy tr) phuong
trinh hdi qui fting'6)
4 Tt phrrong trinh hdi qui ta nhdn tha-v
4-etyi pyridin ld chat c6 khi ndng rlc che
an mdn tdi nhdt (td'c d0 in mdn R""- =
0.12937gim'zh)
J U
TAI LIEU THAI{ KHAO
[1] Trdn Hi6p Hii - Hodng Van H,:ng Cc ch€'d,n mdn uci m6i quan hd u6i hoa hoc Itrng tu - H6i nghi di6n h6a Todn Quoc (2002)
l2l Trdn ThAi Hda, Luan ud,n ti\n si hoa hoc - Trtiong DHKHTN (2002),
[3] i\guy€n Minh Thio, Hoa hoc cac hqp chat di udng Chrrong b NXB GD (2000)
t4l V.S, Saslri* and J.R Perumaredd.i**, Corrosion Science, Vol.50, No.6, pp.432.437 (1994)
i5l Reza Pavaherdasshii, Anti-Ccr:-osion Methods and Materials, y6T 47 No.1, pp.30-34 (2002)
[6] Corrosion inhibitors, Chapter 10 ( 2 0 0 0 )
l7l CRC Hand,book of chemistry and, physics- A ready-reference booh of chemical and pltysical data - Tgthod_ Boca Ratcn N.Y: CRC press, iSBN 0-8493-0478-4 (1997)
[8] Hyper Chem Release 7.0 for Windows, Molecular Modeling Sysiem,
F T r r n e r n r r h o T - ^
f r J
[9] Sfatgraphics 6.0 for Dos
2-etyl pvridin 2 5 4 1 4 9 q 7 1 q R 0 1 9 8 3 0 2 4 5 1 1 9 0 0 6 0 2 4 7 7 4 3-etyl pyridin 2 5 5 8 9 9 Y t t t x 0.7712 - 0 i 9 4 117.592
I I O U O D
0 2 5 8 5 7
9 < A A t r , ' l
9 9 7 3 9 0 2 0 5 3 - 0 2 3 i 0.72937
zN G(<C3NC,) R"or"6 ropyridin 2 4 0 4 9 3 1 1 1 2 0 -i354.444 - 0 0 7 2 3 I T O J J / 0.2822-0
J - n lropvrid n / - + ! , l o f 1 1 1 3 7 1 3 6 5 4 5 8 0 1 3 8 3 1 1 7 9 5 3 0 2 4 0 1 8
tropyridin 247.413 r 1.c3 L l a 9 / r O - 0 0 9 8 3 1 f i A F , 1 4 2 6 0 1 7