ࡱ>   @A<}{ bjbjzz >(mVV840$T"    3#`E  Y   "'U]vo0#1j#r#6d#V v: 1. Frontier Molecular Orbitals a. Determine how many  real  electrons are in each molecule. For each molecule in the GROUND STATE, indicate which  molecular orbital (1,  2, etc.) is the HOMO and which is the LUMO. Indicate the symmetry of each FMO.  EMBED ChemDraw.Document.6.0  b. Repeat part a assuming each molecule is in an excited state.  EMBED ChemDraw.Document.6.0  2. Electrocyclization Reactions For each reaction: Indicate which  molecular orbital is the HOMO and its symmetry Determine if the ring closure would be conrotatory or disrotatory Draw an arrow pushing mechanism Draw the structure of the major product (include stereochemistry)  EMBED ChemDraw.Document.6.0   EMBED ChemDraw.Document.6.0  3. Cycloaddition Reactions For each reaction: Describe the cycloaddition e.g. [3+3] Determine if the addition would be suprafacial or antarafacial Draw an arrow pushing mechanism Draw the structure of the major product (include stereochemistry)  EMBED ChemDraw.Document.6.0   EMBED ChemDraw.Document.6.0  4. Sigmatropic Rearrangements For each reaction: Indicate which  molecular orbital is the HOMO and its symmetry Determine if the rearrangement would be suprafacial or antarafacial Draw an arrow pushing mechanis<>D* , V X ^ b  > @ B D F H L Z f  ʾʾʢwh\L\h;Xh;X6CJOJQJaJh;XCJOJQJaJh5hKxCJOJQJaJhGX-CJOJQJaJjhGX-UjQU hGX-UVh;Xjh;XUh5CJOJQJaJhKxhKxCJH*OJQJaJhKxCJOJQJaJh.cCJOJQJaJh5h5CJOJQJaJh2U5CJOJQJaJh55CJOJQJaJ> F L ; [ $a$gdZF$a$gd6 $a$gd6^`gd6^`gdQPgdQP dgdKx $da$gdGX- dgd;X dgd^     8 H L r t + / : < Z \ d ˾˱wiia]RjO h6UVh6jh6UhQPhQP5CJOJQJhCJOJQJaJhCJOJQJh6CJOJQJhQPCJOJQJh,+kh^5CJOJQJaJh*5CJOJQJaJh^5CJOJQJaJh2U5CJOJQJaJh*19CJOJQJaJjh;XUj]hGX-UjQU hGX-UV    1 4 5 ; < M U _ j m z ĺuk``XThK!jhK!Uh5[5CJOJQJh5[CJOJQJh.CJOJQJh];CJOJQJhtrCJOJQJh'CCJOJQJh,+kh2U5CJOJQJaJh2U5CJOJQJaJh1eCJOJQJhQPCJOJQJjh6UjO h6UVh6CJOJQJh6jh6Uj5h6U  < {   RTVXZ<gd'C dgdO& $da$gd^^`gd'C^`gdtrgd5[ dgd2U   JLNPRTZ\^xŽйܬxlxbxWbWxUxUh5[5CJOJQJh5[CJOJQJh'CCJOJQJaJh'CCJOJQJh,+kh2U5CJOJQJaJh2U5CJOJQJaJh*5CJOJQJaJh];5CJOJQJaJhO&jph];UjA"O h];UVjh];Uh];hSp hNjhK!UjhK!Uj/O hK!UVm Draw the structure of the major product Describe the rearrangement e.g. [3,3]  EMBED ChemDraw.Document.6.0   EMBED ChemDraw.Document.6.0      CHEM 302 - Dr. Hartel Winthrop University Problem Set 11  Pericyclics PAGE  PAGE 2 T68:<>BDHJNPTV dgd#w $da$gd^ $da$gd$^`gd'CT.024<>@DFJLPRVƾݲј݁yuyuyuyulcWh hK!5CJ aJ hGX-5CJaJ hGX-5CJ aJ hZ]jhZ]Uh8h^CJOJQJaJjb[h&]Uj'O h&]UVh yh&]CJOJQJaJhCJOJQJaJjfAh&]Uj'O h&]UVh&]jh&]Uh yhCJOJQJaJh.CJOJQJhmUzCJOJQJV $da$gd^ &`#$gd#w$a$gd#w $da$gdGX-   Ǹh8h^CJOJQJaJhZ]hGX-0JmHnHu hK!0JjhK!0JUhK!h hK!5CJ aJ hK!5CJ aJ <P1h:p#w/ =!"#$% Dp]Dd )llb  c $A? ?3"`?"]8ͼX7pXGtl\Dg@=\8ͼX7pXGtlgg9\x ^EOzIw@eCH "$I DCb,L,,-#(ʰ# .hH`dAQYīxC,u=×aEQDvΪ8NܶSm#bX}Ê_.{bZMQ| <=5踿Fz(M(qο'αfϦâ(>WL{]Ub^V]58XU,+m{?\@6Ekqw1mZ^oDoAٽhc7xj\ߞPzx(:}gMGwwkz6ꌢ;}~ȿOmy{tjlW*&csV ^VՎ?a3Jzֽ w(̩$fE[jkuP'G3DĽ{u˽ҳQ1qط~^W"vv'q{0}eWlu6ڥ=NdL/s*iB<l{_1?)fpR:p?>?e4^}XoR|D.۽:yT|w|0}eꇜ1u?=?3񔝿qKl7'Ɯ|BE7FzܫcڿLFaWkQCA]1-5WS3f1Zrx]ębu]ڡy3ڤn+?nTV^h>x헾 @|3 }d>a[򓘸ԷOn~6=;J?N~_ZRTZ*n>cCGơuےĥMvWh7Qٽ`W7,{)=2_ߗ(fbu=I_3m[)N>v6Np>}6k觭=OٹAR<+ bG9Xy ~3-k^/'E~b|T8d` 6{Zƃ?x_'#[=S;uULG@/Ξm1~ y~*{爢X]<zܝr|;y njk~Ǘ965׋IOIl{~hMg yRv??l]Pv[1ql:v&x*;ךG͡2SWG^J>_T\sol-5-6U}E_mV΁l3 LkqT^7-7盾Kܽx[u߸a6??ZMIqo3~kn944C+F 6\/ۜϼߍ~߆p~~=-s][Ns1Ē+\1~&6\z ΊkƐ¶TmlCFx.}]Dq"7y칱lp??Ʈ+Ew^ o<7o.v)hX1cBH-ۻ  \#5xj1ř]w1Rqg?K6a1ñh5| CسAB{}͇n>LkQ Cٷ (Q>+p̘RLl,v-(j b)6!{ܷlz p6Kol2½+P6\zzu_+}bi;p-vލ6ּX(v}pna|HgP:f;[qP֩=p<@jۆ}|A(![:Mdy<jA YЦt}tdl,2hf}ΊK3fdFYnhSo2칎 –bͰxX\FY\aI[:;>td3׆q.^m*ɰ${E-ԂҌ҈\R;]ֻ qR]Yn{N,5PE=(3x6ºc ٜ?(>[:4_c|Gq((>[:=:;1JulK>?^ҋ⳥Yn`%ۋ⳥] U#$JeN+eKt)?216BX-΍=>–bb {O7–bn8s1t i^L̰ߊȞt{!!^aO(![:mN`f~YUNCu>f~݌-`ΰ;[:%fG;tԳ;2Ŏ}|-^awe'86t;o)/wt{:2QpꐊʵJf\S8fAsŗPF܀B H?;#$%&'()*+,-./0123456789:;<=>*CDEFGHIJKLMNOPQRSTUVWXYZ[\]^_`abcdefghijklmnopqrstuvwxyz{|}~Root Entry, F#'U]!Data yWordDocument+>(ObjectPool.!'U]#'U]_1431423105!mA. 'U]'U]Ole ObjInfoCONTENTS":9    VjCD0100ChemDraw 8.0Microsoft Word - C:\Users\hartela\Documents\Courses\CHEM 302\CHEM302Webpage\chem302home_files\Problem Sets\PS11 - Pericyclics.doc %U f̌ @1 :;<  w `  QzG"x# $$$$8 @@%Times New RomanSymbolxXXjdVg(XXd'`&"5&$$#m"h#f. 7#. 7#/ 7#fB 7#/ 7M$;U 7O$fFg 7# ## $## ## $ ## N$$$ ## N$ #M$ P$ M$O$T$C---Q$I 7S$" 7U$}-Z8 7W$" 7Y$I  7[$}JZ8 7]$ Q$S$ ^$ S$U$ ]$_$_$ U$W$ `$ W$Y$ a$ Y$[$ b$ [$Q$ a$]$z$+Fvw$aӦ6+ 7y$l6+  7{$9>  7}$lFQ  7$aӦFQ  7$>  7l%9c 07n%lOv 27%c N7$ w$y$ $$$ y${$ $ {$}$ $m%$ $$ %$$ $w$ m% 1}$l% o% 3l%n%% O$% $V Meq*c$IM 7$0*M 7$0*&c 7$I&c 7$ $$ $ $$ $ $$ $$$ $$ Q%3TiN%/ 7P%/ 7R%8# 7T%T 7V%N 7X%h  7Z%S !7\% "N%P% ]% #P%R% \%^%^% $R%T% _% %T%V% ^%`%`% &V%X% a% 'X%Z% b% (Z%N% a%\%e%/ &d%R&/P )7f% *7h%R& ,7j%n .7g% +d%f% i% -f%h% g%k%k% /h%j% }%*'Nc|%$/+ 47~%= 57%$yP 77%.c 97% 6~%|%% 8%~% % :%%%ti% ;7%s <7%@hi =7%s >7% ?7% 5i @7%@hb F7%s( G7%( H7% 5b I7% A%% %%% B%% % C%% %%% D%% %%% E%% % J%% % K%%% L%%% M%% %'$F).PvO%'J1 T76&];b&XDL0&=?1 +CY5];b&(DCY5#`OH1&=?NG 3MCB];B'lCDL# `M2&T/< +"X/8*P/8X/0C#`O:3& 0&1&'M).'$F).PvO#HOMO:%'GQ6%'Kȁ b77&<bPZDS%@ȁ Y+D<b(D#`OH%@ Z3MD<'DDS# `M%JV/H [+"*Z/Q/PZ/#`O:% \%%'dO'GQ6#HOMO:%'Gȩ=Q^%'KAA p78&<bs6PZD\%@AA g+DD<bs6(DD#`OH%@V h3MDZR<ZR'DD\# `M%JV/L i+"*Z/pHQ/pHPZ/R#`O:% j%%'dOȩ='Gȩ=Q^#HOMO:%'dHȩPR%'DLA ~79&=bs[D%}AA u+]E=bs(E#`OH%}A v3M]EZ=Z'ED# `M% W/ w+"Z/pjR/p[/#`O:% x%%'$Pȩ'dHȩPR#HOMO:%? . 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TTBPT@1@.LP: % % M % M % M  TT X(fT@1@M LPH8   TT*X2fT@1@ LPO8   TT3X>fT@1@ LPMK  TT?XGfT@1@LPO8 K TTIXKfT@1@KLP  ` TTLXRfT@1@`LPS,  TTTXZfT@1@LPy,  TTZXbfT@1@LPm8  TTdXlfT@1@LPm8 8 TToXtfT@1@8LPe& ] TTuXxfT@1@]LPt t TTxX{fT@1@tLPr  TT}XfT@1@LPy,  TTXfT@1@LP: % % V H % V H % V H  TT"o(}T@1@V H LPL,  H  TT*o2}T@1@ H LPU8  H  TT3o>}T@1@ H LPMK H  TT?oG}T@1@H LPO8 KH  TTIoK}T@1@KH LP  `H  TTLoR}T@1@`H LPS, H  TTToZ}T@1@H LPy, H  TTZob}T@1@H LPm8 H  TTdol}T@1@H LPm8 8H  TToot}T@1@8H LPe& ]H  TTuox}T@1@]H LPt tH  TTxo{}T@1@tH LPr H  TT}o}T@1@H LPy, H  TTo}T@1@H LP: % % % %  TT[,c:T@1@LPH8  TTd,l:T@1@LPO8 4 TTn,y:T@1@4LPMK ~ TTz,:T@1@~LPO8  TT,:T@1@LP: % F6% % V,89HH% %  % %   % '%  % ( % F-6-% % V,NNH//+H+% %  % %   % '%  % ( % F6% % V,deHH% %  % %   % '%  % ( % F6% % V,"#HH% %  % %   % '% F CDIFVjCD0100ChemDraw 8.0Microsoft Word - C:\Users\hartela\Documents\Courses\CHEM 302\CHEM302Webpage\chem302home_files\Problem Sets\PS11 - Pericyclics.doc U f&̌ , :;<  w `  QzG"x# $$$$8 @@%Times New RomanSymbolxXXjdVg(XXd'`&T5&$$#;h#. 7#. 7#]/ 7#B 7#*M/ 7M$)M;U 7O$Fg 7# ## $## ## $ ## N$$$ ## N$ #M$ P$ M$O$T$C---Q$I 7S$" 7U$}-Z8 7W$" 7Y$I  7[$}JZ8 7]$ Q$S$ ^$ S$U$ ]$_$_$ U$W$ `$ W$Y$ a$ Y$[$ b$ [$Q$ a$]$z$Q+vw$h6+ 7y$6+  7{$X>  7}$FQ  7$hFQ  7$%>  7l%Xc 07n%Ov 27%$c N7$ w$y$ $$$ y${$ $ {$}$ $m%$ $$ %$$ $w$ m% 1}$l% o% 3l%n%% O$% $V Meq*c$IM 7$0*M 7$0*&c 7$I&c 7$ $$ $ $$ $ $$ $$$ $$ Q%ÜTBviN%5 7P%5 7R%R8# 7T%CT 7V%] 7X%Ch  7Z%RS !7\% "N%P% ]% #P%R% \%^%^% $R%T% _% %T%V% ^%`%`% &V%X% a% 'X%Z% b% (Z%N% a%\%e%/ &d%R&/P )7f% *7h%R& ,7j%n .7g% +d%f% i% -f%h% g%k%k% /h%j% }%*'Nc|%$/+ 47~%= 57%$yP 77%.c 97% 6~%|%% 8%~% % :%%%tNHi%i ;7%1 <7%i =7%1 >7%i ?7%ʘi @7%b F7%1( G7%i(F CDIF H7%ʘb I7% A%% %%% B%% % C%% %%% D%% %%% E%% % J%% % K%%% L%%% M%% %~C).K~MvO%~qG1 T76&8b&K>VsL0&<1 +@Y58b&~@Y5#`OH1&<NG 3M@B8B@sL# `M2&7R/< +"V/8M/8K>V/0C#`O:3& 0&1&~QK).~C).K~MvO#HOMO:%~EKN6%~Hȁ b77&K:bKWsS%+>ȁ Y+ BK:b~1B#`OH%+> Z3M BK:YBsS# `M%S/H [+"W/O/KW/#`O:% \%%~L~EKN6#HOMO:%~Eȩ=KN^%~HAA p78&K:bs6KWs\%+>AA g+ BDK:bs6~1BD#`OH%+>V h3M BZRK:ZRYBs\# `M%S/L i+"W/pHO/pHKW/R#`O:% j%%~Lȩ=~Eȩ=KN^#HOMO:%~EȩKO%~IA ~79& ;bsK~Xs%>A u+B ;bs~B#`OH%> v3MBZ ;ZCs# `M%wT/ w+"WX/pO/pK~X/#`O:% x%%~Mȩ~EȩKO#HOMO:%.ffO%1 7:&M3&kEL%M1 +MI5M3&I5#`OH%Mf>G 3MMfBMfBEL# `M%ex< +"E88k C#`O:% %%~..ffO#HOMO:%>ٵ+f&%q 7;&Mx3EC%MXq +M8 Mx3^ #`OH%MXf 3MM8fMxf܆EC# `M%8 +"E#`O:% %%ٵ>ٵ+f&#HOMO:%>=+f^%1A 7<&Mx3c6E\%MX1A +M8DMx3c6^D#`OH%MXfV 3MM8fJRMxfJR܆E\#F CDIF `M%K +"`HE`HR#`O:& %%=>=+f^#HOMO:&f&1 7=&M83cE&M1 +MM83c#`OH&Mf 3MMfJM8fJFE# `M& +"``#`O:& &&f#HOMO:%?:/ s2/ ?<vO P&ChemDraw can't interpret this label.1# of p Electrons:%[bC/TbC/]vO Q&ChemDraw can't interpret this label.LUMO:%KNlKdovO R&ChemDraw can't interpret this label.HOMO Symmetry:%}6u6QtvO S&ChemDraw can't interpret this label.LUMO Symmetry:%;/P3/P=6 ^&ChemDraw can't interpret this label.1# of p Electrons:%O]bUb|_6 _&ChemDraw can't interpret this label.LUMO:%Km܉Kf܉p6 `&ChemDraw can't interpret this label.HOMO Symmetry:%?wQ6 a&ChemDraw can't interpret this label.LUMO Symmetry:%;/3/=^ l&ChemDraw can't interpret this label.1# of p Electrons:%O]b>Ub>|_^ m&ChemDraw can't interpret this label.LUMO:%KmKfp^ n&ChemDraw can't interpret this label.HOMO Symmetry:%?wQ^ o&ChemDraw can't interpret this label.LUMO Symmetry:%</4/> z&ChemDraw can't interpret this label.1# of p Electrons:%^bOVb<` {&ChemDraw can't interpret this label.LUMO:%KnKfBq |&ChemDraw can't interpret this label.HOMO Symmetry:%?xQ }&ChemDraw can't interpret this label.LUMO Symmetry:&m M mgfO &ChemDraw can't interpret this label.1# of p Electrons: &33/=33/)gfO &ChemDraw can't interpret this label.LUMO: &{   / ffO &ChemDraw can't interpret this label.HOMO Symmetry: &f&-f&ffO &ChemDraw can't interpret this label.LUMO Symmetry: &@M @g& &ChemDraw can't interpret this label.1# of p Electrons: &}33g& &ChemDraw can't interpret this label.LUMO:& ̉;̉ f& &ChemDraw can't interpret this label.HOMO Symmetry:&mff!f& &ChemDraw can't interpret this label.LUMO Symmetry:&M g^ &ChemDraw can't interpret this label.1# of p Electrons:&}3>3>g^ &ChemDraw canF\ N CDIF't interpret this label.LUMO:& ̌;̌ f^ &ChemDraw can't interpret this label.HOMO Symmetry:&mff!f^ &ChemDraw can't interpret this label.LUMO Symmetry:&Mg &ChemDraw can't interpret this label.1# of p Electrons:&=3}3ig &ChemDraw can't interpret this label.LUMO:& ̌̌of &ChemDraw can't interpret this label.HOMO Symmetry:&-fmff &ChemDraw can't interpret this label.LUMO Symmetry:H$u}x|u}R  %Kx|KR U %[x|[R V %lx|lR W %m:x|m:R X %~8~ ] %*M8*M c %C]8C] d %n8n e %mQ<8mQ< f %~~a k %*M*Ma q %C]C]a r %nna s %mQ<mQ<a t %ǵǵ y %MM  %^^  %nn  %m=m=  &h|R  &h|R  &h|R  & h| R  &h|R  &"("  &W(W  &p(p   &I (I   !&~(~  "&""a  #&WWa  $&ppa  %&I I a  &&~~a  '&  (&  )&00  *&    +&>>  FDMHCGRTSO x9 `: j: jU:+ +jV:| |jW: jX: T ]:Tc:ITId:Te:Tf:  k:q:IIr:s:t: ){ &,y:){&,:X){X&,:){&,:){&,: i:0 0i:r ri: i: i:2S2:NSN:S:S:S:22:NN::::A)zA&+:])z]&+:)z&+:)z&+: )z &+ #|#~p~bT "2;w"2<O#=w%> %? #@O&Fw( G ( H &I]45I79#.)&$*&,&'.|)|*   | *!KK mtm L tY Y  L0tE2 ND-D FFZ 2    A B C D E JKL M68:+-/"#$%& ' (!""##$$!%&&''()**%(+1+,3)-O.//00112233.45567884799:HOMO:HOMO:HOMO:HOMO:HOMO:HOMO:HOMO:HOMO:  V#[#[%  Gsi  G44s  )U3  #]t#]:%  e+k  6e6+  G 5    P5# of p Electrons:  ,QW5LUMO:  v*R*5HOMO Symmetry:   @S 7@ 5LUMO Symmetry:     ^ # of p Electrons:  JL_LuLUMO:   ` HOMO Symmetry:   a U 'LUMO Symmetry:    1l1k# of p Electrons:  JmukLUMO:  `n`kHOMO Symmetry:   vo Uv 'kLUMO Symmetry:     z %# of p Electrons:  Y#s{#s%LUMO:  |%HOMO Symmetry:   } d  6%LUMO Symmetry:    84# of p Electrons:  s4LUMO:  ("(3HOMO Symmetry:  >>P3LUMO Symmetry:     V # of p Electrons:  JJLUMO:   @ HOMO Symmetry:  8  nLUMO Symmetry:    0V0j# of p Electrons:  jLUMO:  ^@^iHOMO Symmetry:  8ttniLUMO Symmetry:     e )%# of p Electrons:  #q#q%LUMO:  O %HOMO Symmetry:  G  }%LUMO Symmetry:Times New RomanSymbol@@FDMHC#O#H()A-GDIC. X]YTimes New RomandLUMO Symmetry: 0 !% 摑Ct D !% 摑Ct D !% CtD !% P&Dt D !% CtD !% UDsD !% XDt D  '(. ' '(. ' ' '(. 0 !% yDC !% yDjtC !% 8#EktC !% 3 EjtC !% 3 EC !% 8#EGA  ' '(. ' ' ' '(. 0!% Bj;E-CD !% Bj;E.CD !% >GE.D !% 9RE.CD !% 9RE-CD !% >GE.þD !% 6}^E.D !% 1.jE.CD !% 6}^E-þD  '(. ' '(. '(. ' ' '(. ' 0!% 8PEMC !% 8PEjC !% 83^EjC !% 83^EMC  ' ' '(. ' 0!% wD/D !% <E/D !% 6E*D !% 4 EuTD !% ; EtD !% DuTD !% D*D  ' '(. ' '(. ' ' '(. 0!% EƜC !% EŜC !% jEƜC !% BEŜC  ' '(. ' 0!% PCC !% blDC !% Q0IDC !% >wDC  '(. ' '(. 0!% ȈEC}D !% ȈED}D !% EDD !% yED}D !% yEC}D !% EDD !% REDD !% *ED}D !% *EC}D !% REDD  '(. ' '(. '(. ' ' '(. ' (. '  0!HOMO:!O%b CD !% tD2DD !O% vTDMD  '"4HOMO:6= C2D < 0!HOMO:!O%b :DkD !% iEkD !O% ;ZDKQD  '"4HOMO:6= :D[6D < 0!HOMO:!O%b HEkD !% AVEkD !O% OEKQD  '"4HOMO:6= HE[6D < 0!HOMO:!O%b EKD !% PEKD !O% E+SD  '"4HOMO:6= E;8D < 0!HOMO:!O%b wC0'E !% 2D0'E !O% ,D0E  '"4HOMO:6= wC0E < 0!HOMO:!O%b D0 E !% _E0 E !O% FD0E  '"4F MDLSKHOMO:6= D0E < 0!HOMO:!O%b HE0 E !% 7VE0 E !O% {OE0E  '"4HOMO:6= HE0E < 0!HOMO:!O%b E0 E !% KE0 E !O% E0E  '"4HOMO:6= E0KE <0 5 0 5 0 5 0 >5> 0 L5L 0 *  0 *  0 *  0 * MM 0 * [[ 0 w  0 w  0 w  0 wM M 0 w[ [ 0  0    0  0 TT 0 bb 0  4  0  4  0  4  0 a 4a  0 o4o 0 )    0 ) ' '  0 )   0 ) p p  0 ) ~~ 0 w   0 w' '  0 w  0 wp p  0 w~ ~ 0    0 . .  0    0 x x  0  % ( % CONTENTS+:9_1333796330!mA. 'U]'U]Ole EPRINTVjCD0100ChemDraw 8.0Microsoft Word - C:\Users\hartela\Documents\Courses\CHEM 302\CHEM302Webpage\chem302home_files\Problem Sets\PS11 - Pericyclics.doc U f&̌ , :;<  w `  QzG"x# $$$$8 @@%Times New RomanSymbolxXXjdVg(XXd'`&T5&$$#;h#. 7#. 7#]/ 7#B 7#*M/ 7M$)M;U 7O$Fg 7# ## $## ## $ ## N$$$ ## N$ #M$ P$ M$O$T$C---Q$I 7S$" 7U$}-Z8 7W$" 7Y$I  7[$}JZ8 7]$ Q$S$ ^$ S$U$ ]$_$_$ U$W$ `$ W$Y$ a$ Y$[$ b$ [$Q$ a$]$z$Q+vw$h6+ 7y$6+  7{$X>  7}$FQ  7$hFQ  7$%>  7l%Xc 07n%Ov 27%$c N7$ w$y$ $$$ y${$ $ {$}$ $m%$ $$ %$$ $w$ m% 1}$l% o% 3l%n%% O$% $V Meq*c$IM 7$0*M 7$0*&c 7$I&c 7$ $$ $ $$ $ $$ $$$ $$ Q%ÜTBviN%5 7P%5 7R%R8# 7T%CT 7V%] 7X%Ch  7Z%RS !7\% "N%P% ]% #P%R% \%^%^% $R%T% _% %T%V% ^%`%`% &V%X% a% 'X%Z% b% (Z%N% a%\%e%/ &d%R&/P )7f% *7h%R& ,7j%n .7g% +d%f% i% -f%h% g%k%k% /h%j% }%*'Nc|%$/+ 47~%= 57%$yP 77%.c 97% 6~%|%% 8%~% % :%%%tNHi%i ;7%1 <7%i =7%1 >7%i ?7%ʘi @7%b F7%1( G7%i( H7%ʘb I7% A%% %%% B%% % C%% %%% D%% %%% E%% % J%% % K%%% L%%% M%% %~C).K~MvO%~qG1 T76&8b&K>VsL0&<1 +@Y58b&~@Y5#`OH1&<NG 3M@B8B@sL# `M2&7R/< +"V/8M/8K>V/0C#`O:3& 0&1&~QK).~C).K~MvO#HOMO:%~EKN6%~Hȁ b77&K:bKWsS%+>ȁ Y+ BK:b~1B#`OH%+> Z3M BK:YBsS# `M%S/H [+"W/O/KW/#`O:% \%%~L~EKN6#HOMO:%~Eȩ=KN^%~HAA p78&K:bs6KWs\%+>AA g+ BDK:bs6~1BD#`OH%+>V h3M BZRK:ZRYBs\# `M%S/L i+"W/pHO/pHKW/R#`O:% j%%~Lȩ=~Eȩ=KN^#HOMO:%~EȩKO%~IA ~79& ;bsK~Xs%>A u+B ;bs~B#`OH%> v3MBZ ;ZCs# `M%wT/ w+"WX/pO/pK~X/#`O:% x%%~Mȩ~EȩKO#HOMO:%.ffO%1 7:&M3&kEL%M1 +MI5M3&I5#`OH%Mf>G 3MMfBMfBEL# `M%ex< +"E88k C#`O:% %%~..ffO#HOMO:%>ٵ+f&%q 7;&Mx3EC%MXq +M8 Mx3^ #`OH%MXf 3MM8fMxf܆EC# `M%8 +"E#`O:% %%ٵ>ٵ+f&#HOMO:%>=+f^%1A 7<&Mx3c6E\%MX1A +M8DMx3c6^D#`OH%MXfV 3MM8fJRMxfJR܆E\# `M%K +"`HE`HR#`O:& %%=>=+f^#HOMO:&f&1 7=&M83cE&M1 +MM83c#`OH&Mf 3MMfJM8fJFE# `M& +"``#`O:& &&f#HOMO:%?:/ s2/ ?<vO P&ChemDraw can't interpret this label.1# of p Electrons:%[bC/TbC/]vO Q&ChemDraw can't interpret this label.LUMO:%KNlKdovO R&ChemDraw can't interpret this label.HOMO Symmetry:%}6u6QtvO S&ChemDraw can't interpret this label.LUMO Symmetry:%;/P3/P=6 ^&ChemDraw can't interpret this label.1# of p Electrons:%O]bUb|_6 _&ChemDraw can't interpret this label.LUMO:%Km܉Kf܉p6 `&ChemDraw can't interpret this label.HOMO Symmetry:%?wQ6 a&ChemDraw can't interpret this label.LUMO Symmetry:%;/3/=^ l&ChemDraw can't interpret this label.1# of p Electrons:%O]b>Ub>|_^ m&ChemDraw can't interpret this label.LUMO:%KmKfp^ n&ChemDraw can't interpret this label.HOMO Symmetry:%?wQ^ o&ChemDraw can't interpret this label.LUMO Symmetry:%</4/> z&ChemDraw can't interpret this label.1# of p Electrons:%^bOVb<` {&ChemDraw can't interpret this label.LUMO:%KnKfBq |&ChemDraw can't interpret this label.HOMO Symmetry:%?xQ }&ChemDraw can't interpret this label.LUMO Symmetry:&m M mgfO &ChemDraw can't interpret this label.1# of p Electrons: &33/=33/)gfO &ChemDraw can't interpret this label.LUMO: &{   / ffO &ChemDraw can't interpret this label.HOMO Symmetry: &f&-f&ffO &ChemDraw can't interpret this label.LUMO Symmetry: &@M @g& &ChemDraw can't interpret this label.1# of p Electrons: &}33g& &ChemDraw can't interpret this label.LUMO:& ̉;̉ f& &ChemDraw can't interpret this label.HOMO Symmetry:&mff!f& &ChemDraw can't interpret this label.LUMO Symmetry:&M g^ &ChemDraw can't interpret this label.1# of p Electrons:&}3>3>g^ &ChemDraw can't interpret this label.LUMO:& ̌;̌ f^ &ChemDraw can't interpret this label.HOMO Symmetry:&mff!f^ &ChemDraw can't interpret this label.LUMO Symmetry:&Mg &ChemDraw can't interpret this label.1# of p Electrons:&=3}3ig &ChemDraw can't interpret this label.LUMO:& ̌̌of &ChemDraw can't interpret this label.HOMO Symmetry:&-fmff &ChemDraw can't interpret this label.LUMO Symmetry:H$u}x|u}R  %Kx|KR U %[x|[R V %lx|lR W %m:x|m:R X %~8~ ] %*M8*M c %C]8C] d %n8n e %mQ<8mQ< f %~~a k %*M*Ma q %C]C]a r %nna s %mQ<mQ<a t %ǵǵ y %MM  %^^  %nn  %m=m=  &h|R  &h|R  &h|R  & h| R  &h|R  &"("  &W(W  &p(p   &I (I   !&~(~  "&""a  #&WWa  $&ppa  %&I I a  &&~~a  '&  (&  )&00  *&    +&>>  t-Ios;=%dKgM.udG Y9Bm8udsMbsf^ Y6he40oE=SPBtʋ)TǞa3/RgsYvt{=f^F {c/ˠmG1x3/cQXbwCˋ)bf^ ̋ ->鷐-ew.ΙRͼӡ ז\A5cϋ5{wP@9lE,[:Y9%s6dsRgME=߱Y9Ц"?H،ݐ-LӡŮET߄cz|ܢcc{tU,V|g.hcmD淭cϵ9Fuu<=5{mעu]vMByGMO͘x{qC?6駳Q4*Q5MґcۣsO=D<]\?]eLb?x^;?-(T9aj2Lm t:F\6iOzg178?Կf\˔)Co $F,1kMz~jykZ¶0e_i5tr7G uz6Q6a&b2ڧ/Fl2ތmж}\_!'(![:ڔ32"l,rhS8&c?aKg۠ }>Qձ?+]T(cDuq9;e J W|Jgw \\Ŵbc\=W:mІ{W,td%dKggB'2wt{%)aޱaKgAێ"VX>u䏸> ŧt{)4)6adWcЧ֑c3Ǯk32z-έWgأo"l,j؝cfػ:"l,:Qbq Lt;DߵEwկ2Ru5uNW^09wEax-I!O9~ :9Bt1? 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Ąs݋l8i-=~jT^mckuwD?}>真.w~Z_J ]O@LZ4iv駗F4X:+{#O`es=ٺo-,Ն'[ݓX4v~ 0OGZ=9c[/U臢 s3O9g"l,*%7dؗ8"l,RpG&}Ȥ/UC^cS'׀6:!82_i74b >_V+_cɱaKgu}C-^{q}coK@_+8/ΰor["l, {c-Ǿ5–bwZGɰos#l, Ǿ+–b]A-ν{2>c?aKgOڼ LkaKg'Akǚ{ wOºz4پr ׋pι6yuurs}csl,<' e[:e7![̰ٱ7EYsKn,v6E릟ېR>g>ϿaKgWg2{[:s淔86bs,$-s5yE~WKoɗp̼uY("Rk[JECt{-^Q![:mLͼV^Lf^ ̋Ї; PRlECtƚSk9*d3/b-s]9F&f^ ҡ*k ԧ|}ͼH6bȖ/3lE7EY%wȯBiCa~K7"̋Y.Go)6"̋![::f~Kf^ Y\˰plŐ-ŞkQ X)ϋi|7E~{b~wOl?6Om(͈g#fwY4xzlwOL?=OFO 9oR~sO 9a`ct=?. s 0gc=ޱaKgT'D>$–b{J; ʱmݽglUPHY'KgS?OͰ${J-ŮB܏aQ}OkԵZG#p}zjoo=h_>.H[>bFY)`b29[:+–b2[:vU6\[.اCogd[:mLvݍ׆ŷ:gv\|f7'']x-ӡKK1b Yy`ODQh`!:v>dKgg@?->7caKgg1KY <~1akGح†p},ǞVJg2/v}pwEYޝa۱ع9˱joBy>hs,vi1=-–bW(( M ܴ{N-Ş }j ӱعnͰɤxKgW@c\S@6CȖ/X'SUaKggg86Bعg32l2ODYЧ/˰qln,v.ΙRM&f^ YXl?Ӆu~^T];{Æqyqt-ӡIUosͼH6bȖbσ>^0̋d3/l, Sto)6"̋![:=3c7[ͼH6bȖbWylŐͼHŶbͼH6sTf^[/Rl2f^ Yv>o)6"̋![RlECt{ b3/]Чr[M&̋![::f~Kf Y\3dͼؽɋw`v+ $:l+!G EMF@  l 0 rKRp8Times New Roman<  <d/ ||H<|<|84X |<0`<0X8H<X<|L ||||<|dv%   &% !/6! % &% (  >= % ( '% &% <>6< >= % ( '% (  % ( % &% !6= % &% (  >= % ( '%  % ( % &% =6Y % &% (  >= % ( '% &% 6L >= % ( '% (  % ( % &% X/6 % &% (  >= % ( '% &% KF6 >= % ( '% (  % ( % &% 6!/ % &% (  >= % ( '%  % ( % &% !/6 % &% (  >= % ( '%  % ( % &% 6] % &% (  >= % ( '%  % ( % &% 63B % &% (  >= % ( '% &% 6@Z >= % ( '% (  % ( % &% ]69 % &% (  >= % ( '% &% M6G >= % ( '% (  % ( % &% 6N % &% (  >= % ( '%  % ( % &% S6 % &% (  >= % ( '%  % ( % &% S6 % &% (  >= % ( '% &% 4b6 >= % ( '% (  % ( % &% 6a % &% (  >= % ( '% &% 46B >= % ( '% (  % ( % &% 6RT % &% (  >= % ( '%  % ( % &% a6R % &% (  >= % ( '%  % ( % &% ? 6?  % &% (  >= % ( '%  % ( % &% ? 6  % &% (  >= % ( '% &% Z 6  >= % ( '% (  % ( % &% ? 6  % &% (  >= % ( '% &% Z 6  >= % ( '% (  % ( % &%  6x  % &% (  >= % ( '%  % ( % &% ? 6  % &% (  >= % ( '%  % ( % &%  6  % &% (  >= % ( '%  % ( % % % V0*.% % 6% % V,^,,% %  % %  >= % '%  % ( % % % V0% % 6% % V,^% %  % %  >= % '%  % ( % % % V0z  z o z % % z 6z % % V,^| | x x % %  % %  >= % '%  % ( % % % V0z~zznz% % y6y% % V,^{|||xx% %  % %  >= % '% % Rp8SymbolX$ |(|"|||/ (|"|||((C0<8<@<"|<< |\4P\x|<<X(|<l| ||||<|dv% 6h %  % ( % 6h RpTimes New RomanM@O@2|@@rҠ9w@鵾G@B)X@XDA>A aw@H4P<q:<|X< ||||<|dv% 6h  TTqw@@6h LPh, % % `h RpSymbol |w؟shI(؟ڟpXSwe@hIwPw @w5 eH4PxV:<|X(<ې ||||<|dv% `h  TTx}@@`h LPn& % % K% K% K TTu}@@KLPD8 % &% % +\xq% % +\ } % % +\% % +\ % % ( % 9% 9% 9 TTrz*@@9LPD8 % % ?i% ?i% ?i TTsl{{@@?iLPD8 % w6w% % V,g^hzzvv% %  % %  ?i % '%  % ( % 6% % V,$[$% %  % %  ?i % '%  % ( % / 6/ % % V,_1 1 - - % %  % %  ?i % '%  % ( % 6% % V,\% %  % %  ?i % '%  % ( % w6 w% % V,g hzzvv% %  % %  ?i % '% % %  % ( % %  TTi#w@@LPH8 U TT$i,w@@ULPO8  TT.i9w@@LPMK  TT:iBw@@LPO8  TTCiEw@@LP  , TTGiLw@@,LPa& Q TTMiSw@@QLPn, { TTSiYw@@{LPd, % % $% $ TTw @@$LPs& :$ TT w&@@:$LPy, c$ TT'w/@@c$LPm8 $ TT1w9@@$LPm8 $ TT;w@@@$LPe&  $ TTAwD@@ $LPt  $ TTEwH@@ $LPr <$ TTIwO@@<$LPy, % % % %  TThv@@LPc&  TThv@@LPl  TThv@@LPo,  TThv@@LPs&   TThv@@ LPu, 5 TThv@@5LPr Q TThv@@QLPe& % 6% % V,$$% %  % %  Q % '% % l%  % ( % l% l TT&"4@@lLPH8 Ol TT#&+4@@OlLPO8 l TT-&84@@lLPMK l TT9&A4@@lLPO8 l TTB&D4@@lLP  &l TTF&K4@@&lLPa& Kl TTL&R4@@KlLPn, ul TTR&X4@@ulLPd, % % %  TT4B@@LPs& 4 TT4%B@@4LPy, ] TT&4.B@@]LPm8  TT048B@@LPm8  TT:4?B@@LPe&  TT@4CB@@LPt  TTD4GB@@LPr 6 TTH4NB@@6LPy, % % xf% xf% xf TT%3@@xfLPc& f TT%3@@fLPl f TT%3@@fLPo, f TT%3@@fLPs& f TT%3@@fLPu, (f TT%3@@(fLPr Df TT%3@@DfLPe& % / 6 / % % V, 1 1 - - % %  % %  Df % '% %   %  % ( %   %    TT$@@  LPH8 \  TT%-@@\ LPO8   TT/:@@ LPMK   TT;C@@ LPO8   TTEG@@ LP  3  TTHM@@3 LPa& X  TTNT@@X LPn,   TTTZ@@ LPd, % %   %    TT!@@  LPs& @  TT!'@@@ LPy, j  TT(0@@j LPm8   TT2:@@ LPm8   TT<A@@ LPe&   TTBE@@ LPt &  TTFI@@& LPr B  TTJP@@B LPy, % %  %  %   TT@@ LPc&   TT@@ LPl   TT@@ LPo,   TT@@ LPs&    TT@@  LPu, 5  TT@@5 LPr Q  TT@@Q LPe& % 6% % V,% %  % %  Q  % '% %  C%  % ( %  C%  C TT!@@ CLPH8 IC TT"*@@ICLPO8 C TT,7@@CLPMK C TT8@@@CLPO8  C TTAC@@ CLP   C TTEJ@@ CLPa& EC TTKQ@@ECLPn, oC TTQW@@oCLPd, % %  %   TT@@ LPs& - TT$@@-LPy, W TT%-@@WLPm8  TT/7@@LPm8  TT9>@@LPe&  TT?B@@LPt  TTCF@@LPr 0 TTGM@@0LPy, % % r=% r=% r= TT@@r=LPc& = TT@@=LPl = TT@@=LPo, = TT@@=LPs& = TT@@=LPu, "= TT@@"=LPr >= TT@@>=LPe& % F CDIFVjCD0100ChemDraw 8.0}3= B g&g @@3 :;<   `  QzG"x# $$$$8 @@%Times New RomanSymbolxXX$dg(XX$d'`&$$! +H!$ӡ" S!ӡ" T7!~V5 U7!_ H V7!$_ H W7!JWV5 X72&KW ^7! Y!! !3&!! Z!! ! [!!! \!!! ]!! 3& _!2& P&,&CSEO&31 `Q&H1 a7S&33(4D c7U&efS4D e7W&33(: g7R& bO&Q& T& dO&S&V& fQ&U&X& hO&W& Y&(}!IGZ&@! i7[&! j7\&3st4 l7]&et4 n7c&?)G p7e&)G r7_& kZ&[& `& mZ&\& _&d&a& o[&]& _&f&d& q\&c& f& s]&e& g&(Dj?Kh&@O@& ti&d@& u7j&3sD8 w7k&eo8 y7l&?OK {7w&3sD: }7y&?8 7n& vh&i& o& xh&j& x&n&q&p& zi&k& n&z&q& |j&l& x& ~h&w& z& k&y& &3Vlb``3l&Z@e 7`^b3Vlb``3l&ChemDraw can't interpret this label.#``hn&Ydffk&@@h + 7f&4eYdffk/An atom in this label has an invalid valence.# `D&3bf=ti&7f + 7ff;b3bf=ti/An atom in this label has an invalid valence.# `D&Ytcff4j&@f + 7f&cYtcff4j/An atom in this label has an invalid valence.# `D&u!@m!3Q &ChemDraw can't interpret this label. HOMO and symmetry&@tl@v3s &ChemDraw can't interpret this label.closure&! 3sP &ChemDraw can't interpret this label. HOMO and symmetry&@3 &ChemDraw can't interpret this label.closure&"@"33@R &ChemDraw can't interpret this label. HOMO and symmetry&3s &ChemDraw can't interpret this label.closure&1@ @) 3=P &ChemDraw can't interpret this label. HOMO and symmetry&@0@(@@233 &ChemDraw can't interpret this lFCDIFabel.closure&='z=5T     &E'zE5T     &Ȗ`'zȖ`5T     &''z'5T     &@@   &@C@   &@@   &]@ @   &jTj@  &@Q@  &T  &&R&  &j@j  &@@  &@  &&&@   && P& Y& & && Y& g& & && g& ! & && ! & &FDMHCGRTSBx9 `   ' '*)%& }*A }*u }*D }:RR :ece::+r+:RR :ewe : :+h+ 'Vi%1tuXswsy0{X}hs-ijTln,pr`a#TcTe#gg&S(T)^*U(V&W%*X%>^vxz| ~  k m o qsbdfhYZ[\]_DDDhn `` 'b&'L `` = `` j`` `` _   $ !^ HOMO and symmetry    >z > =closure  74O HOMO and symmetry  (  Pbclosure   v!sm HOMO and symmetry   g > > closure  ++9,@ HOMO and symmetry  + +* +SclosureTimes New RomanSymbol@@F MDLSKXY Times New RomanV 0 OD/Xc_Times New RomandHOMO and symmetry 0 =XOKTimes New Romandclosure 0 G ' Xc_Times New RomandHOMO and symmetry 0  ( XOKTimes New Romandclosure 0 V6Xc_Times New RomandHOMO and symmetry 0 GXOKTimes New Romandclosure 0 @ hXc_Times New RomandHOMO and symmetry 0 XOKTimes New Romandclosure 0 !% )CG[E !% )CGE !% XDG{E !% n4DGE !% n4DG[E !% XDGE !% BCGE  '(. ' '(. '(. ' ' 0 !% CC !% C5D !% *DC !% *DPD !% "CC  ' '( '(. ' 0 !% CD !% CE !% #DPD !% #D E !% 1DD !% 1DE  ' '(. '(. ' ' 0 !% @CQE !% @C_E !% cDJE !% cDeE !% '=DQE !% DpCCJE !% cDGsE  ' '(. '(. ' ' ' 0!hn }DXE  0!H% PDD  0!H% D D  0!H% pDTE 0 kJk89d20 J89d20  J 89d20 J89d20 >Q  0 > Q  0 >Q :  0 >BQ  0 H)) 0 1  0 O 0 9 0 J) ) 0 ;   0 J  0 4 % % ObjInfoCONTENTS_1333796353 !mA. 'U]'U]Ole VjCD0100ChemDraw 8.0}3= B g&g @@3 :;<   `  QzG"x# $$$$8 @@%Times New RomanSymbolxXX$dg(XX$dd'`&8$$! +H!$ӡ" S!ӡ" T7!~V5 U7!_ H V7!$_ H W7!JWV5 X72&KW ^7! Y!! !3&!! Z!! ! [!!! \!!! ]!! 3& _!2& P&,&CSEO&31 `Q&H1 a7S&33(4D c7U&efS4D e7W&33(: g7R& bO&Q& T& dO&S&V& fQ&U&X& hO&W& Y&(}!IGZ&@! i7[&! j7\&3st4 l7]&et4 n7c&?)G p7e&)G r7_& kZ&[& `& mZ&\& _&d&a& o[&]& _&f&d& q\&c& f& s]&e& g&(Dj?Kh&@O@& ti&d@& u7j&3sD8 w7k&eo8 y7l&?OK {7w&3sD: }7y&?8 7n& vh&i& o& xh&j& x&n&q&p& zi&k& n&z&q& |j&l& x& ~h&w& z& k&y& &3Vlb``3l&Z@e 7`^b3Vlb``3l&ChemDraw can't interpret this label.#``hn&Ydffk&@@h + 7f&4eYdffk/An atom in this label has an invalid valence.# `D&3bf=ti&7f + 7ff;b3bf=ti/An atom in this label has an invalid valence.# `D&Ytcff4j&@f + 7f&cYtcff4j/An atom in this label has an invalid valence.# `D&u!@m!3Q &ChemDraw can't interpret this label. HOMO and symmetry&@tl@v3s &ChemDraw can't interpret this label.closure&! 3sP &ChemDraw can't interpret this label. HOMO and symmetry&@3 &ChemDraw can't interpret this label.closure&"@"33@R &ChemDraw can't interpret this label. HOMO and symmetry&3s &ChemDraw can't interpret this label.closure&1@ @) 3=P &ChemDraw can't interpret this label. HOMO and symmetry&@0@(@@233 &ChemDraw can't interpret this label.closure&='z=5T     &E'zE5T     &Ȗ`'zȖ`5T     &''z'5T     &@@   &@C@   &@@   &]@ @   &jTj@  &@Q@  &T  &&R&  &j@j  &@@  &@  &&&@   && P& Y& & && Y& g& & && g& ! & && ! & &EPRINTObjInfoCONTENTS-&_1333800879&!mA. 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w7j!oN? x7k!0, y7{&`R 7}&մ`R 7&e 7&oNe 7l! zf!g! q!m!m! {g!h! n! |h!i! m!~&p! }j!k! |&q!q! ~k!f! |& j!{& ~& i!}& & }&&& {&&r!/*&>& ;&=& @& 9&?& !0ʹi!j0 7!xj0 7!E0wC 7!x+V 7!+V 7!P0wC 75&Ph 77&Eh 7! !! !!! !! ! !! !8&! !! 6&!! !! 6& !5& 8& !7& A&/f9B&3@ + 7ff74/f9/An atom in this label has an invalid valence.# `D&t;[bR*n&oij &~j 7&t07# 7&~5 7&oi5 7&A^07# 7&A^H 7&tH 7&~U[ 7&oiU[ 7&A^ 7&A^E n 7&tE n 7& && &&&& && & && &&& && &&& && & && & && & && &&& && &&& && & && & && &j4ft&n + 7ffrtj4ft/An atom in this label has an invalid valence.# `D&4F<0CDIFf& + 7fft4f/An atom in this label has an invalid valence.# `D&7633f &ChemDraw can't interpret this label. HOMO and symmetry&3 &ChemDraw can't interpret this label.closure&@s4k43d &ChemDraw can't interpret this label. HOMO and symmetry&rjt3 &ChemDraw can't interpret this label.closure&@@--3] &ChemDraw can't interpret this label. HOMO and symmetry&3 &ChemDraw can't interpret this label.closure&,@,3s@\ &ChemDraw can't interpret this label. HOMO and symmetry&@@@33 &ChemDraw can't interpret this label.closure!'5y o    !:':5y p    !Ȗ'Ȗ5y q    !gt'gt5y r    &@V@   &@@   &Z@   &@   &@_@%  &a@'  &igi@-  &g.  &  &hh  &  &@@@   && ! r! !  & r! e! ! A&& e! & ! && & ! &FDMHCGRTS#x9 ` f4o f1xo4o1xp$4o$1xq14o11xr*3=.5a*'`="5a*=S5a*= 5a:45/v45*:(_/(_+:>0 >+:0+:;7#:/;/7#:(_;(_7#:4q;4q7$r20205)J1)J2*1,605,6/]*/]-2-1/"05/"/]'/]0203 + B+-E B. . -E 0101+W+W,/,/.}.}^/W/$2* t%* u&+v%,w$2,x#Z+y#Z.o&.o%/$2/ 2s       !z!"{"#|$%}% ~$&#''(&)DDD*hn `` $2$#2$3? `` 020S213? `` S223N`` ``  -2 2 U3j  ,L',G0 HOMO and symmetry  8O8O:closure  ,f,/ HOMO and symmetry  8OW8O:closure  )1+(+*./D HOMO and symmetry  )"8O(8O)J:closure  5+z4l+u6/5 HOMO and symmetry  54814815\:sclosureTimes New RomanSymbol@@F0#MDLSKXY Times New RomanV 0 #Xc_Times New RomandHOMO and symmetry 0 ' HmXOKTimes New Romandclosure 0 3Xc_Times New RomandHOMO and symmetry 0 '+HXOKTimes New Romandclosure 0 KXc_Times New RomandHOMO and symmetry 0 'CHXOKTimes New Romandclosure 0 6Xc_Times New RomandHOMO and symmetry 0 L9XOKTimes New Romandclosure 0!hn FEFD  0!% 4EȐE !% 4EE !% ? EE !% EE !% EȐE !% ? EhE !% :EhE !% :EE !% EE !% EȐE  '(. ' '(. '(. ' ' ' '(. ' (. 0!% \E=@E !% \EME !% ?5E}TE !% ?5E}9E !% ?E}9E !% ?E}TE !% EJE !% ͿE2E  '(. ' ' '(. '(. ' ' 0!% &>& ;&=& @& 9&?& !0ʹi!j0 7!xj0 7!E0wC 7!x+V 7!+V 7!P0wC 75&Ph 77&Eh 7! !! !!! !! ! !! !8&! !! 6&!! !! 6& !5& 8& !7& A&/f9B&3@ + 7ff74/f9/An atom in this label has an invalid valence.# `D&t;[bR*n&oij &~j 7&t07# 7&~5 7&oi5 7&A^07# 7&A^H 7&tH 7&~U[ 7&oiU[ 7&A^ 7&A^E n 7&tE n 7& && &&&& && & && &&& && &&& && & && & && & && &&& && &&& && & && & && &j4ft&n + 7ffrtj4ft/An atom in this label has an invalid valence.# `D&4f& + 7fft4f/An atom in this label has an invalid valence.# `D&7633f &ChemDraw can't interpret this label. HOMO and symmetry&3 &ChemDraw can't interpret this label.closure&@s4k43d &ChemDraw can't interpret this label. HOMO and symmetry&rjt3 &ChemDraw can't interpret this label.closure&@@--3] &ChemDraw can't interpret this label. HOMO and symmetry&3 &ChemDraw can't interpret this label.closure&,@,3s@\ &ChemDraw can't interpret this label. HOMO and symmetry&@@@33 &ChemDraw can't interpret this label.closure!'5y o    !:':5y p    !Ȗ'Ȗ5y q    !gt'gt5y r    &@V@   &@@   &Z@   &@   &@_@%  &a@'  &igi@-  &g.  &  &hh  &  &@@@   && ! r! !  & r! e! ! A&& e! & ! && & ! &Ole EPRINT=ObjInfo CONTENTS    0lyM%F EMF  @  T  ~ JKRp8Times New Roman<  <d/ ||H<|<|84X |<0`<0X8H<X<|L ||||<|dv%   &% b 6b  % &% (    % ( '%  % ( % &% T 6  % &% (    % ( '% &% b 6    % ( '% (  % ( % &% b 6  % &% (    % ( '% &% } 6     % ( '% (  % ( % &% b 6  % &% (    % ( '%  % ( % &% O6O} % &% (    % ( '%  % ( % &% O6o % &% (    % ( '% &% j6   % ( '% (  % ( % &% O}6 % &% (    % ( '% &% jm6   % ( '% (  % ( % &% o6 % &% (    % ( '%  % ( % &% 6| % &% (    % ( '%  % ( % % % V0*-     % %  6~ % % V,,, } }  % %  % %    % '%  % ( % % % V0 G Q G ; G % %  F 6~ F % % V, I } I } E E % %  % %    % '%  % ( % % % V0  %   % %  6~ % % V, } }  % %  % %    % '%  % ( % % % V0y}  %   % %  6~ % % V,{| } }  % %  % %    % '% % Rp8SymbolX$ |(|"|||/ (|"|||((C0<8<@<"|<< |\4P\x|<<X(|<l| ||||<|dv%  %  % ( %  RpTimes New RomanM@O@2|@@rҠ9w@鵾G@B)X@XDA>A aw@H4P<q:<|X< ||||<|dv%   TT+G@@ LPh, % %  RpSymbol |w؟shI(؟ڟpXSwe@hIwPw @w5 eH4PxV:<|X(<ې ||||<|dv%   TT+G@@ LPn& % %  - %  - %  -  TTG@@ - LPD8 % &% % + % % + $% % + T N % % + % % ( %  %  %   TTG@@ LPDP8 % %  %  %   TTl{G@@ LPDdO8 % 6 % % V, hWh   % %  % %    % '% % D o%  % ( % D o% D o TTi#wG@@D oLPc& i o TT$i&wG@@i oLPl[  o TT'i-wG@@ oLPo,  o TT.i3wG@@ oLPs&  o TT3i9wG@@ oLPu,  o TT:i=wG@@ oLPr o TT>iCwG@@oLPe& %  6 % % V,&U&  % %  % %  o % '% % 8  %  % ( % 8  % 8   TT'!5G@@8  LPc& ]   TT"'$5G@@]  LPl t   TT%'+5G@@t  LPo,    TT,'15G@@  LPs&    TT1'75G@@  LPu,    TT8';5G@@  LPr   TT<'A5G@@ LPe& % 6 % % V, W  % %  % %    % '% % D %  % ( % D % D  TT#G@@D LPc& i  TT$&G@@i LPl   TT'-G@@ LPo,   TT.3G@@ LPs&   TT39G@@ LPu,   TT:=G@@ LPr  TT>CG@@LPe& % 6 % % V,T  % %  % %   % '% % 8 %  % ( % 8 % 8  TT!G@@8 LPc& ]  TT"$G@@] LPl t  TT%+G@@t LPo0,   TT,1G@@ LPs&   TT17G@@ LPu,   TT8;G@@ LPr  TT<AG@@LPe& % &%  6V % &% (   % ( '% &%  6V  % ( '% (  % ( % &%  V6  % &% (   % ( '% &%  e6   % ( '% (  % ( % &%  6> e % &% (   % ( '%  % ( % &%  V6>  % &% (   % ( '% % %  % ( % %  TT\&b4G@@LP+, % % ?% ?% ? TTntG@@?LP+, % &%  x6  % &% (  ? % ( '% &%  x6  ? % ( '% ( % W %  % ( % W % W  TTagG@@W LP+, % &% t 6t  % &% (  W  % ( '% &%  6  W  % ( '% (  % ( % &%  V6  % &% (  W  % ( '%  % ( % &%  6 e % &% (  W  % ( '%  % ( % &% * 6* _ % &% (  W  % ( '% &% E 6E S W  % ( '% ( RpTTimes New Roman |(|_| <t ||||<|84Ph |L4P<}X< |\ ||||<|dv%  G%  % ( %  GRpTimes New RomanZ&G@h@.M.M6; m@ Pu@awk@(Xi@a ` @4P<v<|X<  ||||<|dv%  G TTN\G@@ GLPC2  G TTN\G@@ GLPO8 % RpTimes New Roman|TOT`hXUUUUe@ `@m@|_@QXUUUUe@`hXUUUUM@ QXUUU4P<SX<$X ||||<|dv%  WRpTimes New Roman |(|"|||D<"|H<Ppj<y P `@HtH  4P<@AvXH< `@ ||||<|dv%  W TTT]G@@ WLP2 % %  G%  G TTN\G@@ GLPC2 @ G TTN\G@@@ GLPH8 % % t W% t W TTT]G@@t WLP3 % % & % * 6 D % & % (  t W % ( ' % %  %  % ( %  %   TTG@@ LPC2   TTG@@ LPO8 % %  %   TTG@@ LP2 % %  %   TTG@@ LPC2 @  TTG@@@ LPH8 % % t % t  TTG@@t LP3 % % & % * _6  % & % (  t  % ( ' %  % ( % & % 6_ % & % (  t  % ( ' %  % ( % & % 6D % & % (  t  % ( ' % & % 6[ t  % ( ' % (  % ( % & % _6 % & % (  t  % ( ' % & % O6 t  % ( ' % (  % ( % & % 6[P % & % (  t  % ( ' % % C!%  % ( % C!% C! TTQpW~G@@C!LP+, %  6 % % V,Hhh     % %  % %  C! % ' % % o%  % ( % o% o TTeihwG@@oLPt o TThinwG@@oLPy,  o TToiuwG@@ oLPp, + o TTvi{wG@@+ oLPe& %  6 % % V,F&&   % %  % %  + o % ' % %  %  % ( %  %   TTb'e5G@@ LPt   TTe'k5G@@ LPy,   TTl'r5G@@ LPp,    TTs'x5G@@  LPe& %  6 % % V,H    % %  % %     % ' % % %  % ( % %  TTbeG@@LPt  TTekG@@LPy,  TTlrG@@LPp,   TTsxG@@ LPe& %  6% % V,E  % %  % %    % ' % % %  % ( % %  TTbeG@@LPt  TTekG@@LPy,  TTlrG@@LPp,   TTsxG@@ LPe& % F CDIFVjCD0100ChemDraw 8.0|4K 4sL @@3 :;<   `  QzG"x# $$$$8 @@%Times New RomanSymbolxXX$dg(XX$d'` ,$${+)uBn@o4=|+Nv }+zdv 7~+0D;~ 7+bGo;~ 7+0D 7+ |+}+ + |+~++ }+++ |++ +HߑA+v 7+zv 7+0;> 7+bG;> 7+ 7+z 7+ ++ + ++ +++ ++ +++ ++ + ++ +0tvO@(Z+`vR 7@vO0tvO@(Z&ChemDraw can't interpret this label.#``hn+zOvRcYvY+`SvIV + 7cGWv=SzOvRcYvY/An atom in this label has an invalid valence.# `D+v}Qcv=X+vT + 7cvQv}Qcv=X/An atom in this label has an invalid valence.# `D+z~v}Qcv=X+`vT + 7cGvQz~v}Qcv=X/An atom in this label has an invalid valence.# `D+c;`+`v 7+cv 7+ +++QmA?}:+v' +:v' +c<~: 7+0Է<~: 7+0Է 7+c 7+ ++ +++++ ++ + ++ + ++ + ++ +dG?+/+z- 7+dGz- 7+ +++nME*" !c%+ !c $ 7+nM $ 7+ +++NgHVD+zv 7+zv 7+kz( 7 ,VԁP@+o y+ct) z+xqc+xE # `O+T~~7+ {+J (թzJ'ԁ~S.# `O+xP@ |+FZa! } + ~+++ +++ +++ ++n%Ng%NpVD#`CO2CH3+z( 7,w+ aH,S$ ,k +k + k# `O,?3 +!y0ݔ906# `O,aH ,1)   , ,, , ,,, ,,, ,,3%%VD#F  CDIF`CO2CH3+ ++ +++ ++ + ++ +un|45C}+z +z 7+$pJ 7+WGJ 7+$pT 7+ ++ + +++ +++ ++ + v`v | &ChemDraw can't interpret this label.closure+v v  &ChemDraw can't interpret this label.closure+ &v`v (| &ChemDraw can't interpret this label.closure+v  v  &ChemDraw can't interpret this label.closure+v  v-ܯ  5This label has conflicting or unassignable charges. ++ {`{Im/ 5This label has conflicting or unassignable charges. ++ a\  T խ^o 5This label has conflicting or unassignable charges. ++ `mo 5This label has conflicting or unassignable charges. ++! a   &ChemDraw can't interpret this label.type+ I ! &ChemDraw can't interpret this label.type+ !&  aI  ( &ChemDraw can't interpret this label.type+a I  &ChemDraw can't interpret this label.type+1hb?B     +fZ1hfZb?B     +ŷ1hŷb?B     +H1hHb?B     +`vivIt   + v`vIt   +`zv=vIt   + v`vIt   +`vI`v  +vv   +`vI`v  + v  vI  +a0a  +I/  + a0 a  + . ~   ,, ++ {++ + +, {++ ++ + +, ++ ++ + +, ++ + +F DMHCGRTS/6x9 `#,#,&#&,2#2,*4%:0@*)%:$[*%:*^%: :{#-{:#:*7#-*7:6:#6:}:{{L:.:*7*7L:6X6X13I0.4!.0B13I0h04{0'%4\\72/&,r%'% (i%v'v)Q--QA      ! "#CO2CH3CO2CH3DDDhn ``000V ``4414V `` 2}b1]2 `` &zb%]& `` 5{`` `` ?1:   >f"closure  `!closure  **_+""closure  66b7%!closure  Qxs+  &&c',+  7e4+  222D+  >pXtype  `+type  **_+,+type  767M+typeTimes New RomanSymbol@@F MDLSK XY Times New RomanV 0  3 XOKTimes New Romandclosure 0 bXOKTimes New Romandclosure 0 / XOKTimes New Romandclosure 0 1XOKTimes New Romandclosure 0 9 t ?XC?Times New Romand+ 0 1 XC?Times New Romand+ 0 _ N XC?Times New Romand+ 0 " rXC?Times New Romand+ 0 } , 8 XIETimes New Romandtype 0 f b XIETimes New Romandtype 0 f / XIETimes New Romandtype 0 f @ XIETimes New Romandtype 0 !% ELQE !% E^E !% nEJE !% nEeE !% EJE  ' '( '(. ' 0 !% U EOE !% U EOFE !% EO&E !% EOE !% #EOE !% #EOFE  ' '(. '(. 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' ' 0!% E\E !% EE !% EE !% ḫEE !% EqE !% ~E 4sL @@3 :;<   `  QzG"x# $$$$8 @@%Times New RomanSymbolxXX$dg(XX$dd'`(8$$1'4l2' l+ 7lt4l/An atom in this label has an invalid valence.# `D3'p&t4'  q+ 7pp&t/An atom in this label has an invalid valence.# `D'h3sr' l z+ 7spsh3sr/An atom in this label has an invalid valence.# `D(_ W͉ (33j9KW 7 (9KW 7(j 7(ƴ| 7(33jƴ| 7(ff_j 7(ff_i 7(  ( ( (  (( ( ((( (( ((( ( ( ( (( 1(NI2(+3: R +7ČNN+:'U# `O3(̟: R 74(d 75(̟tw 76(+3tw 77(^fd 78(^f) 7O() 79( 2(3( :( 3(4( ;( 4(5( :(P(<( 6(7( >(=(=( 7(2( >( 6(8( P( 5(O( ?(1L @(.3;_ +7njt\4\.;b# `OA( ;_ B(@r 7C(  7D(.3 7E(af@r 7G(sL 7H( @(A( I( A(B( J( B(C(K( D(E(L( E(@( N( A(G( T(jS3%IEYQ(:F S(f&%F U(y 52 7W(3/т% 7Y(lA 52 7`(YtY 7b(̌EtY 7d(f&%)l 7f(:)l 7j(̌ER~ 7l(YR~ 7n(f&% 7p(: 7[( Q(S( \( S(U( ]( U(W( ^( W(Y( _( Y(Q( a( S(`( c( Q(b( e( `(d( a(m(g( b(f( c(k(k( f(j( m( d(l( o( l(n(q( j(p(($f.s(( + 7f,$f.s/An atom in this label has an invalid valence.# `Du'  < s&ChemDraw can't interpret this label.closurev'8 @@0 @:<3 u&ChemDraw can't interpret this label.closurew'     < w&ChemDraw can't interpret this label.closurex'd @] @f<3 y&ChemDraw can't interpret this label.closure'g@f@x |&ChemDraw can't interpret this label.type'@Cd;dEv ~&ChemDraw can't interpret this label.type'ddv &ChemDraw can't interpret this label.type'"dU"]T"@g@f &ChemDraw can't interpret this label.type}'urguru h    ~'gu i    'gu j    '.g.u k    'L < m  '  < w n  '  < o  ' <T p  ' "  r '@. !@. @ t '  "   v '[ @ [ x '@@ @Q { '99 O } ' @Q  ' [y [ @?   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