Estereoqumica

Cuarta parte
NOMENCLATURA DE ESTEREOISOMEROS

Pedro Antonio Garca Ruiz

Catedrtico de Escuela Universitaria Area Qumica analtica Profesor Titular de Universidad Area Qumica Orgnica

Departamento de Qumica Orgnica - Universidad de Murcia

CONTENIDO
TIPOS DE ISOMERIA ESTEREOISOMEROS COFORMACIONALES ESTEREOISOMEROS CONFIGURACIONALES NOMENCLATURA DE ESTEREOISOMEROS

NOMENCLATURA DE ESTEREOISOMEROS - PROYECCION DE FISCHER - SISTEMA D -L -REGLAS DE CAHN-INGOLD-PRELOG - OTROS SISTEMAS DE DESIGNACION

PROYECCION DE FISCHER

Ideado en 1891 por Emil Fischer, consiste en:

Adoptar el convenio de sobre dos rectas perpendiculares, proyectar los grupos de forma que aquellos que se representan en la vertical, estn detrs del plano del papel, mientras que los que se representan en la horizontal lo estn por delante de dicho plano

PROYECCION DE FISCHER

40I1712] 1712 DSt [5 I SP 492] 103] 766] 722] 406] 080] 033] 437] 049] 712] 489] 360] 263] chemdict begin 5311 2049 DSt [6 I 5311 2437 DSt [11 I 8622 1766 D 41906] 4 20 2699] 2149] 5311

W0pxey-1pCAtr/dy24.6sqrt180pp2opyfillne127 gslpgr}b/OB{/bSape-0.4pxlWpgr}ie}b/ xpend}b/Db{bs{dppx0xe0negSAxmx-1.6cpo163p1l27mpst225.839scsm}b/CB{np[{[{ 75atlCambridgemx/dx-4.8alComputing,wxcmcmL/mv/moveto0.524.6nH-2pdvlt{e yrad80m20chemdict 04p2o0.6 wCBeq{dpdef/b{bindbLpst}]elWxx}ifix4Bdlpgsxglpd/w 8yDA}{dLdvstm}b/dA{[3rO1r6wDDA}{2.25pp}ifelsel2mv0Ssetgraysc1cmOA}{1prp xvxm1rotrolt{-1pycmbegin/version1601dp-1nstcp2or{4fill1r0cpt0r}if180 0a/pxxacwpy 87,012021.6dpdv}{bd}iedp cw-1psglpmvInc.22mvstldef}bindwdv8xrad -1 2go1cmne daL pyL/S{sf2pys0180acLBst}{0 px0lsetgray 1.6sl0smgipy0grm12sDT}]ofill 6current c30-9.6mpyac0p 0g360gspyCBsg2x}ifpnp01sc}b/Ov{OrA1wy4setdash}d/cRsc3LBegs nttomark{bsL/ix/index1dv/bdesgnp[{pycmpsmssm0prOSppdv mat1ro}ie}b/AA{n epnegrO 10180rot02 pxarcdy acpxdvL/mt/matrix270egrSAcpgcmsc2 S}if/lpac 21.6sd o 0eq{DD}{DS}ieneggi0 ac 2.2fillr npa0pprOatdivp0 4.8st 1ala/pycp ppm/aL1dx-1 5 .6n ne{bW0xa}ie}b/WW{gsl1 scedvarcgracmeq{gscplal40.4o pL/m/mulrO Ac}{0 slatepx-1cptOA}{1 5neg}if/px cvbegin0bs pygm1w AA}{1end eq{dL}if rdef}b/d1 c 0 pput lacbscpDLBtype[]type -2 0wyac lgslclippath put DA}{270sgg/cX360gigs1 v DLBl}for 0a}ie}b/BW{wD16 scW0bsly 0 eWI0 fill}b/SA{aF wb pySA9.612lexec x dpdpe0 g-.6-8 6 -1 -1-13 OBeq{DB}{DS}iecmOA}{1.5 acgs opy exec xl3 px0 fi t{bsmt 0 b1aAgr}{gssm0.5 rev{neg}ifppmvpp}{2 40dv/bdcv dp st}{1.04 oaLal9 ill L/ie/ifelse0 st}{Ascarcr S]}b/dL{dAcm pxscst}{Asc ZLBlt{pppx wxpp naps{nH e pypcm smsc 1 scmvx L/l/lineto grfill e p SA px1.5 dprad -1 3 l0 031ix gr -1 x -s A{lW xmv0 12e 3 n/dxssc 0 n/dy1 scm sm acsmduptr lgrrO np gr}b/In{px xsgpx dictbdm/w x 2.2 m gs0mvp SA rO 23gr o g ne{bW e gi SA1 mv ZLB0 o/cXarc2 x 1 m DA}{cw scp r 12 90 CA0OA}{1 sm nex 4 bd pxpp dv a-0.4 L/n/neg B/bLscrad-1 lxl py16 sl 2.25 0.5 cX lxbW 5 cm bs 1 gs p px sc CAAA}{1 l r n 1 gr pbW px 5 DA}{dLpy lp DA}{cw g/wb ro g/bb ac g 1 w x wb sc1.2 n/ey 8 ScientificwF 1 xl}{xl SA 180 npp lp p ne{bW 1.5 dx a SA g l 1 e gs m 25.8 2 begin lrlineto mt sm fill -1 def/L{load lW dp p 0 lW st}{px cY w py p OA}{1 gr}b/wD x xl 4 0 -1 roundDA}{180 lW -1

Hay que visualizar lo que representan:

C A B

currentp

PROYECCION DE FISCHER

Al manejar las proyecciones hacerlo con imaginacin

PROYECCION DE FISCHER
Permutar dos grupos en la proyeccin equivale a hacerlo en la molcula (paso al otro enantimero)

PROYECCION DE FISCHER
Tambin se pasa de un enantimero a otro al girar 90 la proyeccin

PROYECCION DE FISCHER
Dos giros de 90 dos permutaciones conducen al mismo enantimero original

PROYECCION DE FISCHER
Dos giros de 90 dos permutaciones conducen al mismo enantimero original

PROYECCION DE FISCHER
Igualmente mantener un grupo fijo y girar los otros tres conduce al mismo enantimero

NOMENCLATURA DE ESTEREOISOMEROS - PROYECCION DE FISCHER - SISTEMA D -L -REGLAS DE CAHN-INGOLD-PRELOG - OTROS SISTEMAS DE DESIGNACION

SISTEMA

D- L

gr gs 1 54 I 1345 1952 1714] 2606 DSt 2047 1952 2416] ]d 2 1952 1345 4370 1714] [1 1 4370 [12 3122 3425 DSt gr [0 1952 1714 /bs[[1dL [14 50 40 80 40 20 chemdict begin SP DSt [1 211 1201952 I 2464 2580 DSt [13 II 1453 2606 DSt Db I 4370 end 3122 2580 3122 2580] 1822 2606 1453 2606] 4513 2762 4882 3131] 4214 2736 3845 3105] 4552 1904 4921 1904] 1796 1878 1427 1878] 2095 2086 2464 2455] 1033 3425]

x 2 s s{dp In DA}{cw OA}{1bW 1Cambridge DLB neg}if/px s lp 0 lrO wy m2a}b/PT{8ex ac dv m1 p b1 sc 5 -14 mvlos pxsc gr gro a 2-1 psm0 p px2 p lsg0.3 1.2mro0 12esc a -1 de 25.8 eq{dp e 5 bW mv -11.2 p wy aR8 -9.6DA}{cw pym smeL/l/lineto lx arc o g0 pxrO n p 0at 90bdatlne{bW dpgr}{gsarcr 0 1 x}if l cm e -1dvgr}{pp}{gs lpnp pdp cm g-1 a}ie}b/BW{wD0.51 p mvp fill pp}{sqrt neg2.25rPrepeq{DD}{DS}iepx-4.8 lWsg m dvarline gs fill 180 sm-9.6OB81acx DLBx21.60a}ie}b/WW{gs 6 sg wy 1 27 np pAsc dvlppye lnst}b/HA{lW-1pdv l2xl s0 16gsgi0.5 eq{DB}{DS} cp 8ixmv nega}{exrogr sceyrO0cpt0L/ix/index st}{01 fill L/mt/m py sc m mv mv neg}if/py py 0L/S{sfcp0glp begin/versiondplybW dppp -2g exec p5lo counttomark{bsdx24.6ac12dp l16 -2 rpnp 0 -81grlt{1 WI0p1gssl 12ix end}b/Db{bs{dp0sqrt3al 2.2 -1 16nep w st}b/OrA{pybdLasern-1 1 0 pym/w st2.2ScientificOB2begin0acdp -10cmcmscst5stmv pySArad1200CAxOA}{1 type[]type pybegin1s RA}{6dppypscmconocimiento2 py aAdv}{bd}iedv/bd xcWsfillsm SACopyRight mvpp n/ex dictpx180 bsm}b/dA{[3CBrlp rOnp[{pyb l py -9.6-.6wFelaL16.80.60x8 pn/eyac-8SAsc5r0s2.25ppeo0DA}{2.2 ppdprElHA}{dLL/xl/translaterotbW180m360rx2rO 1SAdvsg0bsdel 0wChemDrawlarcngspy aLgrscm1chemdictmvs0.6 wrev{neg}ifgr xl cwl20dvneggrclip}b/Ct{bsdpeexperimentalarcpycwpxcX23cpp L/tr/transformL/gs/gsaveDA}{dLptr/dy1ppDA}{dL Computing,pp L/gr/grestoreatcp0fill1987,L/ie/ifelse0np30-1px0pyacacCAxOA}{10 userdict/chemdict03.375negl}for1.5st}{AscxLBnegCBp0l0cmwxc %dp/cYm12LB1986,145fillnSAputlac0pxne{bW-1dy1n/dycve-1.610o p 2 primer gr-1st}{0 0p mv py 6 g sl sc wF 2 xl}{xl0 In 1 exec}{al np wx m rad p cm p 1180 SADA}{cw o -1 dv dv b2 x np dp CA 1 mv px mt -1 sm 8 x/dx gs0 S]}b/dL{dA m dp bd -.6 pyn/dx o p m fill p 1 px OB/bL sc cv ro lt{-1 180 rot 2 l neg 2 wD np 90 e gs setgra

compuestos quirales parti de una propiedad de estos como es rotar el plano de la luz polarizada, por los que se los llam compuestos pticamente activos
COOH COOH

HO

OH

OH

HO

COOH

COOH

SISTEMA

D- L

gr gs 1 54 I 1345 1952 1714] 2606 DSt 2047 1952 2416] ]d 2 1952 1345 4370 1714] [1 1 4370 [12 3122 3425 DSt gr [0 1952 1714 /bs[[1dL [14 50 40 80 40 20 chemdict begin SP DSt [1 211 1201952 I 2464 2580 DSt [13 II 1453 2606 DSt Db I 4370 end 3122 2580 3122 2580] 1822 2606 1453 2606] 4513 2762 4882 3131] 4214 2736 3845 3105] 4552 1904 4921 1904] 1796 1878 1427 1878] 2095 2086 2464 2455] 1033 3425]

tartratos lt{-1rot 2 x DA}{cw OA}{1bW m mv py 6 g parc 25.8 s lp 0 In In m2a}b/PT{8ex st}{0 0p 2 sm sodiol sl sc 0 pxsc gr grlrO wy -1 s s{dpp px2 1 ac px 1Cambridge DLB neg}if/px eq{dp o a 20 psm0 1.2 p p lsgdv m1 p b1 sc 5 -14arcrlWsg x}if arc 5 bW mv -1pye 0 wy aR8 1.2mro0 12esc a smeL/l/lineto lx l cm o gpp}{sqrt p lnat 900.3 -9.6DA}{cw pym gs mvS]}b/dL{dA e e -1dvgr}{pp}{gs losbdatlne{bW dpgr}{gsamonio1 m p mvp fill fill pxdvlpsepar lpnp pdp cm g-1 a}ie}b/BW{wD0.51 dvarline gs pA180 smneg OB8rPrepeq{DD}{DS}iepx-4.8 CBeq{DB}{DS} np gr scmv n-9.6st}b/HA{lW-1pdv 0a}ie}b/WW{gs 6 sg wy 1 27 cp 8ixmv nega}{exrogr x DLBx21.6l2xl s0 16begin/versiondplybW py sc mg exec neg}if/py py 0L/S{sfcp0glp acgi0.5 l16 fill L/mt/m dppp -2HA}{dLmv counttomark{bsL/ix/index st}{01 -2 rpnp 0 -81cmcmsc mv p5lo 12acsceyrO py stdx24.6sqrt3al r2begin0acdp st}b/OrA{pybdgssl pyix end}b/Db{bs{dp0type[]type -1 16nep w -10Pasteurst5staL16.80.60xpym/w xOA}{15r012dp2.2 pybegin1s RA}{6dp WI0p1Lasern-1 1 08 pn/ey aAdv}{bd}iedv/bdrOnp[{pyb SACopyRight mvpp n/ex rad1200CAbsm}b/dA{[3pycwpxDA}{2.2 l py -9.6-.6 pscm2.251SAdictpx180ac-8SAscy-1s2.25ppeo0cXsfillsm ppdprlt{1pywFelL/xl/translaterotbW180m360rx2rO 1SAdvsg0bsdel 0wChemDrawlarcngspy aLgrscm1chemdictmvs0.6 wrev{neg}ifgr xl cwl20dvneggrclip}b/Ct{bsdpe0cpt02.2ScientificOBlpyxcW23cpp L/tr/transformL/gs/gsaveDA}{dLptr/dy1ppDA}{dL Computing,pp L/gr/grestoreatcp0fill1987,L/ie/ifelse0np30-1px0pyacacCAxOA}{10 userdict/chemdict03.375negl}for1.5st}{AscxLBnegCBp0l0cmwxc %dp/cYm12LB1986,145fillnSAputlac0pxne{bW-1dy1n/dycve-1.610o p -1 dv 2 2 rO 1 dv b2 o exec}{al gr-1 wx x np dp CA np mv dp mtrad p cm gs1180 2 xl}{xl0 m OB/bL -1 -.6 8 x/dx 0 wF SADA}{cw 1 px sc bd de pyn/dx o p m fill p cv ro 180 neg 2 wD np 90 e gs setgra comprob que sus disoluciones desviaban la luz polarizada en el plano en sentidos contrarios
COOH COOH

HO

OH

OH

HO

COOH

COOH

SISTEMA

D- L

gr gs 1 54 I 1345 1952 1714] 2606 DSt 2047 1952 2416] ]d 2 1952 1345 4370 1714] [1 1 4370 [12 3122 3425 DSt gr [0 1952 1714 /bs[[1dL [14 50 40 80 40 20 chemdict begin SP DSt [1 211 1201952 I 2464 2580 DSt [13 II 1453 2606 DSt Db I 4370 end 3122 2580 3122 2580] 1822 2606 1453 2606] 4513 2762 4882 3131] 4214 2736 3845 3105] 4552 1904 4921 1904] 1796 1878 1427 1878] 2095 2086 2464 2455] 1033 3425]

no x 2 s s{dp OA}{1bW m mv p cm p 1180 2 s lp 0 In In DA}{cw p pxex aR8 1Cambridge 6 2 sl sc dospxsc gr grlrO wy m2a}b/PT{82 1 st}{0 m1 2 sm py DLB neg}if/px eq{dp o a 2-1 psmb2 st p p ac dv 1.2 p b1 sc 5 g 4 mvS]}b/dL{dA e 5 bW mv 0 n p 0 wyforma0p mro0 12esc -1-1gi L/l/lineto lx arc o g0 pxdvlp1.2 lnat lsg0.3 -9.6DA}{cw pym sme0.5 1 x}if l cm e -1dvgr}{pp}{gs 90bdatlne{bW dpgr}{gs arc 0 sg m p mvp fill pp}{sqrt neg OB8np pdp cm g-1 a}ie}b/BW{wD0.51 dvarline gs fill 180 -1pye neg}if/py DLBx21.60a}ie}b/WW{gs 6 sg wy 1 27 np pAscmv mv mv lprPrepeq{DD}{DS}iepx-4.8 lWeq{DB}{DS} cp 8ixmv sm-9.6st}b/HA{lW-1pdv l2xl s0 16gs12dp l16 fill L/mt/m py sc-9.6-.6 p5habiacounttomark{bsL/ix/index st}{01 -2 rpnp 0 dppp mg nega}{exrogr x py 0L/S{sfcp0glp begin/versiondplybW -81gr -2HA}{dLaL16.8acsceyrO py stdx24.6acs2.252.2 -1 16nep w st}b/OrA{pybdp5lo 120.60xpym/w xOA}{1 sqrt3al ppbegin0acdp -10cmcmscstsc gssl pyix end}b/Db{bs{dp0type[]type pybegin1s RA}{6dp execm2.251-1 1 08 pn/ey aAcualadearcrCBr2excWsfillsm SACopyRight mvpp n/ex rad1200CAbsm}b/dA{[3pycw o0DA}{2.2 l py rlt{1pywF1LasernSAdictpx180ac-8SAsc5r0lasdv/bdrOnp[{pyb ppdpPeroWI0pelL/xl/translaterotbW180m360rx2rO 1SAdvsg0bsdel 0wChemDrawlarcngspy aLgrscm1chemdictmvs0.6 wrev{neg}ifgr xl cwl20dvneggrclip}b/Ct{bsdpe0cpt02.2ScientificOBlp pxcX23cpp L/tr/transformL/gs/gsaveDA}{dLptr/dy1ppDA}{dL Computing,pp L/gr/grestoreatcp0fill1987,L/ie/ifelse0np30-1px0pyacacCAxOA}{10 userdict/chemdict03.375negl}for1.5st}{AscxLBnegCBp0l0cmwxc %dp/cYm12LB1986,145fillnSAputlac0pxne{bW-1dy1n/dycve-1.610o p 2 rO 1 exec}{al gr-1 wx o -1 dv dv np x CA np dp mv px de rad 8 x/dx gs0 25.8 xl}{xl0 m dp mt saber dv}{bd}ie wF SADA}{cw 1 px OB/bL -1 -.6 pyn/dx o p m fill p sc bd lt{-1 180 cv ro rot l neg 2 wD np 90 e gs setgra estructuras era la que giraba el plano de la luz polarizada a la derecha y cual a la izquierda
COOH COOH

HO

OH

OH

HO

COOH

COOH

24 4422 3585 DSt gr [0 I 3252 2374SP [1 I 5670 2374 1693 5145 3585] 2564 6221 2564] 2538 2727 2538] 2746 3764 3115] 2707 3252 3076] 2005 5670 2374] chemdict begin DSt 5283 4422 40 2374] I 2005 80 40 3252 20

WILBep2lsl0pyixfillm1putpytr/dy0Scientificpyrev{neg}if0rOpyd wmvL/gs/gsave0L/ie/ifelse-8rot360-4.8acppepx1lwyllydef/b{ orea}{exn/ex radne{bW0lpxSA0DA}{dLwF16-10egrfillegrmvn np5parcnfillrPreppydpradlt{-1spy16begin/versiondp arc0acac 6eggrgswysg0.3nSA m-1b1aA2.2180-1xLBnegSAx}iflpmv1o0nSA CApstaL0 gspy aL0m-121.60scmn/dxgssc lW2.2dvnp[{py pxms ypp}{gspxaR8dictbd1801.5dx24.64p0mv25.8 oDA}{cwsc}bp hemdict counttomark{bspy 5 mpx-1or0Computing,ppcmm orm1986,3.375 DLBn/eyac xlpy sc5r0gi0.61l 6 rOsg0 11sm0stg pyscmpp 12-1 1 dppxmvp180 scaneg12dv/bd -2OA}{1pcmsc }{dLL/xl/translate rObWstcp1 lp sqrtdy1n/dymbegindp-11.6 st1.2clip}b/Ct{bs0l}for x0m}b/dA{[3L/l/linetorp23cm wppc 1n-9.6at lpwx sc1pyDA}{cwne{bWx2 rO w 2 xcWcmcp 5 gs 2pylmex 90gr x0l8pcmcpt12 0 ppxarcst}{0 fill16arlinetoc egatLasernSA atey rot1chemdict0type[]type cv 0setgrayW p0bd mv 145 pnegm CAbsnp6 -1mv2.25ac sg dv aclInc.pp rtp px0st}b/HA{lW x rog dpe 3 2 slarc OB lp sc lxnp 27 elp mneg OBst}{0 -9.6L/S{sf 8 DLB acpy CB wDxl}{xl0 p g/wb PT{85 o ro bd end}b/Db{bs{dp smedp cw py -1.6 o g 2n xec l cp16.8ac DA}{dL0 2 L/ix/index 0.5 sg eq{dp bs 3 wF1 ln 1 ac0.60xpsce0lac OA}{1 gs 13 S]}b/dL{dAp 16 c awe neg}if/py 1.2 m/w a}ie}b/WW{gsr beginpbswx gs 2 mv p l 1 dp eq{DD}{DS}ie neg}if/px 0 np 0 at }{al p m8bW gr pp dv a}ie}b/BW{wDSA scXs0 bW l ht OA}{11987, Cambridge g lg s0algs CB DA}{2.25 p np 2.25npcv 120 sm p p gr-1 px mt 2 0 st}{Asc 180 eq{DB}{DS}ie mv dv 1 sc OB/bL ro -1 dv}{bd}ie 90 0.5x fill gr sm -.6 gr}{gs x/dx cm p CA L/mt/matr 2 m p ne cY 2 1 px
CONFIGURACIONES RELATIVAS

SISTEMA

D- L

Hiptesis de Rosanoff
El gliceraldehido que rota la luz a la derecha es el que tiene el OH en la Proyeccin de Fischer a la derecha
CHO CHO

OH

HO

CH2 OH

CH2 OH

D (+)

L (-)

currentpoint

SISTEMA

D- L

CONFIGURACIONES RELATIVAS

Partiendo de la hiptesis de Rosanoff y mediante reacciones que no afectasen al centro quiral, se fueron relacionando los compuestos quirales conocidos, unos con otros. El sistema D -L no estaba libre de fallos pus a veces segn la ruta sinttica por la que se relacionase se llegaba a que un mismo ismero fuese D L

SISTEMA

D- L

CONFIGURACIONES ABSOLUTAS

Fue Bijvoet en 1951 quien comprob mediante difraccin de rayos X sobre cristales de tartrato de Rubidio y Sodio que la hiptesis de Rosanoff era correcta (Tenia un 50% de posibilidades y acert) A partir de ese instante el sistema D - L representa estructuras verdaderas pero nos es un sistema cmodo de utilizar.

SISTEMA

D- L

01952 3122 3425 20 chemdict begin120DSt 50 I 43702580 DSt [13III1952 2416 DSt [3 I 4 22 2736 4921 1904] 13 1904 1427 1878] 14 1878 2464 2455] 96 2086 1952 2416] 95 2047 4370 1714] 52 134540 80 40 DSt gr [0 1952 1 4370 [12 I 2464 40 DSt gr [0 1952 1714 DSt [1 70 [12 I 2464 2580 DSt [13 II 1453 2606 1952 3122 3425 20 DSt [2 1453 2606 DSt Db I St 2756 3845 3105] [14 50 4352 3125] 59 I 1345 1952 1714] 1033 3122 3425] 2580 1453 2580] 2606 4882 2606] gr end1 54 I 1345 1952 1714] 2606 DSt 2086 4921 1904] ]d gs SP [14 [1 1427 1878] [1 2 2095 2047 2464 2455] /bs[[1dL DSt Db 1952 2416] 211 1952 134540 80 1714] chemdict begin SP 1714 1878 3845 3105] 3122 1822 1033 4513 2580 4370 1714 4352 2606 3122 3425] 4214 2756 1453 2580] 4552 2736 4882 2606] 1796 1904 4352 3125]

MOLECULAS CON DOS O MAS CENTROS QUIRALES

mDrawep5ofillaRfilln0mt2bWl2xlne{bWx2-1OBlp1.2OA}{1Prepx8dp20lrOl2scscmm-1pxL/l/linetonp dvnegatclip}b/Ct{bsdpe0dvbsnp5360pp}{sqrtpxmpsl13.375SA00m/wacgrlt{ppmvsc180rlpo-1cX xvpywF1lcpwynSAaLL/ie/ifelse0L/ix/index180acmfillelpwydef/b{bindmAA}{101804wxrOpp63rOOr mscst5pxpat gspy dictpx180ac-8SApnegslt{1sc2LB1986,bW-1radpL/mv/movetopxr0s2.251r2def}b nsformL/gs/gsaveDA}{dLptr/dysc%dp/cYac1165parcncm-1WIdpsc1800aAdv}{bd}iedv/bdaclDA {sqrtscarcnn/ex 1 negl}for1.5dv}{bd}iedv/bdrOnp[{pygrpp}ifelsegitr/dypy16DT}]o10sgpx1l1 mWIpylm2.251ix radbdm1chemdictmv-9.6-.66p-2llmvfill0pxnatst}{AscwyrSg6xgdppydygs2scgDAn r}{pp}{gs03.37508scmv-10dx24.6aclsscpyexec0clip}b/Ct{bs270bWxOA}{1o2arcrixnHSA0ex 6-.6 mv Laser1987,eq{DD}{DS}iewsqrt3dvWIeo0cXatrlinetoDA}{dLp1.58SA360pxa0lppac0.5xsg HA}{dLaL16.8acxpypn/ey 0pxs00mpx02.2512beginsmvp0.60-9.6pygr225.85ppstype[]typexleq{ xec}{alneg}if/py DLBm/w xOA}{1cwgirO Computing,pppxscs pst0pystendsetdash}d/cR1filleg v 120pegs0 lpbWend}b/Db{bs{dp pyarcnegCBmvcmwxixpy0lppxcpac01xlne{bW0s0.6Comput g exec mv counttomark{bs2.2puserdict/chemdict01450xnSAputldvbsnp3-1lpxgspplW-2xo-1bs }b/PT{8ex py-1 sceyputlcpt cpm L/gr/grestoregrcp0acdproclippathg-1g/bbgs-1sqrt3dprOCAopy t/chemdict 120.60xpyx-1g aApyn/dxp 12smnega}{exro0dp mt 0n/ey lal1e0ggr}b/In{pxrev{ne {cwLB1986,145 pdp0DA}{cw0gL/tr/transformL/gs/gsavene{bWcptdv/bdlppyxl44lWAA}{1pp A{pynegpp 90bdatlne{bW 1801180scr1L/l/linetoLaserppy0 negor{4 rad-10p08garcacacmlpsg RightgrL/xl/translaterotpy 0a}ie}b/WW{gsstscDA}{2.252cmxsmmvS40.4msm}b/CB{np[{c mv p-9.6st}b/HA{lW-10CAstm}b/dA{[3mnegcvbegin0oOB/bLlrO0 p 180setgrayLBnegCBp00 1 0 nbdl0OBrogr m1mpac dpepy16begin/versiongr1arccmlp1pydupchemdict0.5S}if/lpSA21.6 p -11.2 nlsl ac0.3 -9.6L/S{sfa}ie}b/BW{wD1 dvsglo 0sgbdscey20pdef}bindodef/L{loadgbegin mnegst 2 1 8rPrep1mrO b1 sc 3 xl 0r0 LBCB-1pyl1aL16.8acstdivOA}{1.5ppx/dxsl18090161xl} dvlppmv p lsgdv 1.2cm 0 12gr}{gsarcrHA}{dLL/xl/translate1DA}{cw4DLBac12g/cX6 px e rO p np st}{0 gr pro-.6 py DLBtype[]type-9.6ppgrnp gsDLBL/S{sfcp m1awb24.6S]}b/dL{ {dp a}{ex np SA rad 8 cm1cmdydvCAnegst}b/HA{lWrottrfill12gr}{gsroundDA}{18 store OA}{1 wx Cambridge 60lpxgsest}{0nbdgs01psmcY p1bdm1b1giDA}{2702CA wgr}ie} dv x sm gr-1 px p 21.6 p x/dxgrpylW00.5ep-1.6acsc}b/Ov{OrAgspyn/dxrxst}{1.0 dv r dp 0 np b2 CA mv dp 120 sm st}{Asc-1px25.8 pOA}{1aRg/wbl roeCA10gr10scL/m/mulcw 4sc w m OB/bL 1 px sc ro cv 8 lt{-1 ScientificmvwFxl}{xlcpSAaLgr -121.60ac scp2escgi0.5pL/n/ne rotppdp mv1 pp0py16pgsrO1.6ne{bW ZLBm2scix execxlgr12 p x m20.5 b2 In -1 0 p np e ex lpl g gr}b/OB{/bS np 5rad-0.4 360 wy 0 2 rO mv fillly e 16 0lW mv1 py ScientificOB x LBa neg}if/px DA}{cw dv eq{gs 2 0p p-1px scpy0 apgs l 5 bW s s{dp pxdppx o cm eq{DD}{DS}ie dv sgcmeq{DB o gfill pdp eq{DB}{DS}ie pp}{2 e a}ie}b/BW{wD pxwb e0 8ix cm sg eq{dp90 lac cp bs lt{-1 ap sclWBd2ppe x}if fill -1 mv r CAcW -1st}{0 ne p4.8 a}ie}b/WW{gs 2 m a gs 4p 0.6 sm sc n fill bW em1 x-1 dp0rO cmx -4.81wF curre nppp o al cw p 0 ne 278 acpx l}for px dv eq{dL}if l dxsne cp CopyRightat wy py w end}b/Db{bs{dpr}if 3ro}ie}b/AA py ChemDrawx dva 01 0.3 1.2wsmst}]e 39OA}{10 gr}b/wD dpgs 0dp 2.2 m p mvnbs 1 py fill}b/SA{aF x}if0mvSA 1 cv lt -8-1x m wF SAst lxnp1grscpsm mp 4 dpalpxDA}{dL 9.6 -2 lx st}b/OrA{py x}if23n/ex dict27ep -.6 1 lWac3lbegin/versionf -12pAmv w 2 -1 rgrm8rInc.msmcm smcp 24.6gs pyCBgs sg d RA}{6180lSAx1 lL/mt/matrixmtst}{pxm}b/dA{[3wn/dyAc} SAsm-2 0n/dysg neg}if/py 3cm1.5 0 stpxwxdvneg}if/px py L l-15sl scgpypxs 0OBl 1987,L/ie/ifelse-8 cptneg 1st}{01 xcm lp rdvgr}{pp}{gs 12 0 m rad dx cv cp 1 m/aLp s{n sc -4.8 2 lp a DA}{cw g 2 exec}{al 2 bs wx mv bL py 2.2 -0.41a/px OA}{ -1 o dv rev{neg}if sm g 4 st L/ix/index al 2.2 cW 2 1 a}b/PT{8p l counttomark{bs st}{Asc-1 0 n wDgi DA}{dL p gs e S]}b/dL{dA at m ro SA p 90 1 dv wD 5 x dp np setgray Cambridge 2.25 5 cv 120 fill a/py sme 1 e aL mv gs sl fill l bd 0 put rot atZLB o/cX o -1 0 25.8 w fill

Con dos centros quirales: Aldotetrosas

Enantimeros
CHO CHO

Enantimeros
CHO H

CHO

OH

HO

HO

OH

OH

HO

OH

HO

CH2 OH

CH2 OH

CH OH currentpoint2 192837465

CH2 OH

currentpoi

D-eritrosa

L-eritrosa

D-treosa

L-treosa

DIASTEROISOMEROS

SISTEMA

D- L

01952 3122 3425 20 chemdict begin120DSt 50 I 43702580 DSt [13III1952 2416 DSt [3 I 4 22 2736 4921 1904] 13 1904 1427 1878] 14 1878 2464 2455] 96 2086 1952 2416] 95 2047 4370 1714] 52 134540 80 40 DSt gr [0 1952 1 4370 [12 I 2464 40 DSt gr [0 1952 1714 DSt [1 70 [12 I 2464 2580 DSt [13 II 1453 2606 1952 3122 3425 20 DSt [2 1453 2606 DSt Db I St 2756 3845 3105] [14 50 4352 3125] 59 I 1345 1952 1714] 1033 3122 3425] 2580 1453 2580] 2606 4882 2606] gr end1 54 I 1345 1952 1714] 2606 DSt 2086 4921 1904] ]d gs SP [14 [1 1427 1878] [1 2 2095 2047 2464 2455] /bs[[1dL DSt Db 1952 2416] 211 1952 134540 80 1714] chemdict begin SP 1714 1878 3845 3105] 3122 1822 1033 4513 2580 4370 1714 4352 2606 3122 3425] 4214 2756 1453 2580] 4552 2736 4882 2606] 1796 1904 4352 3125]

MOLECULAS CON DOS O MAS CENTROS QUIRALES

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Con dos centros quirales: Aldotetrosas

D-gliceraldehido
CHO CHO

CHO

CHO

OH

HO

HO

OH

OH

HO

OH

HO

CH2 OH

CH2 OH

CH OH currentpoint2 192837465

CH2 OH

currentpoi

D-eritrosa

L-eritrosa

D-treosa L-gliceraldehido

L-treosa

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wxlt{1pywFeexec1986,8m1rOeq{DD}{DS}iedyarcac2.2wDlaclmv1lpsm0ne12eg m2exec}{alb2wyLasern0Cambridgesccp0gs20.5-1180cWpbsbegin3divrocmst} 0r20dp/cYml12st}b/HA{lWaLm1acscchemdictrrpscwpyr1dvsc16bspp}ifelselWa pp}{sqrt5rOlst16.8lacradpx0dp-1mcpDLBne{bWComputing,lpL/mt/matrixorg W%s{dpdpnegmst}{0negcmm-1px-.6dp0begin/versionmsmv00gs2egg/wbgipg DA}{cwnscLaserpbWdictmtp0CA180m016-102.251SAosc2setgraypyne27st}{p 2/cYcwl-1LB1mpomv-1fill0gr0end}b/Db{bs{dp3type[]typesnpcmbsclippathl2bd p/OrA{pyg-.6p1.2ac0.601.2m21.62-8-1pscrot16st}{01sg1fillDA}{cwac2w3def} cl userdict/chemdictgs1acradCambridgeslxgrO0n/dycvCBxl}{xlcpcmxcm0sm o L/gr/grestore1lgsOBatPreppmtaA2.2cms4gsscdv/bdwF0123cX0pxstcm2sm270 dvgr}{pp}{gs090SA1DA}{dLdpmv01.5e0plpL/l/lineto2L/mt/matrixpx2dupldp p L/tr/transform3.375aRscdict00lOA}{1L/ix/indexSAxl}{xlnp[{pywpOA}{12 1 xlsmsm-9.6mvcounttomark{bs1dv}{bd}ie5gsr21dvSAox}ifsc}b/Ov{OrAp /grestoremvexgrsgataL-9.6180pprodv180pxarc-1121OBOA}{1Inc.emtL/mv/m opyRightnegnpfill1987,0.6l}form0dx24.6SAs1px w0.5wcXpnefillcmrOpypbsAA} hemDrawOA}{11pyn/expn/eyrOa}ie}b/WW{gsst}{0rlxxrlinetol0bs mtmvst transformscnLBOA}{1pyOB/bLputepyplgr}{gswF16rOnp[{pyfillWImvscgro1. {6wmv180WIatearcnpy-1putbWDA}{cwpygi 180olpppylwyxgr27027cmne{bW mcm-.6scp1986,rost}b/HA{lWtr/dy 1pxpy0-1 sm1l6gs16npcmoacgr-1 fill}b/S ll0a}b/PT{80OBlpnp0xDLBDA}{cwSA360pscsqrt CBsxeSA0psmbWgs0gr}b/O AmdvnegdvaL-9.6ppscgrpxnegrotpy508 mvLBalppppx0lpbeginalp1.6g 1cp pfil dict/chemdictpxmv 90lSAscxpym/w0-8 5r180gsgi 0.5pppxlydef/b{bindptr00 rppdpb2pgrpnpp122.25eq{DD}{DS}iepx5 12425.890eq{DB}{DS}iepy w4 -9.6fillstdvarcnstcppxacix rot8dve0st}{Ascpamv s2.2-2lDA}{2.25ppm lpm lxw -2bWm atsmbdaRmvbWx2ne{bW bsneg pxgs0 alm e-1 ppprlineto SA fill 180WI stL/xl/translate xgrsm m}b/dA{[3 ac2 mx}iffill0p 1 st}{Ascst sc rO p pl-105 n wy 1 py mv stCA180 x/dx lW2.25 gra 0 e 5 pp}{2 1Z px 0exec lp mvPrepnp -9.6 21.6Scientificx scbegin-2 wx g/wbst sm OA p m negx np npmvSA py p 2lcpt a 6 pyCBeq{DB}{DS}ie at 40 cp mv -9.6 pypp p o wx 0 lb1rad 0 -1 n/dxsl sg Computing, 5 cp r s -1 cm cp exm L/ie/ifelse py x py arc r1 0 dv/bd0 wy cY lW e 4 -1 m2 2 2r -1 mv psl ey ey L/ix/index2 S]}b/dL{dA r o at sl p b sc dv 2 mv py 2 sc 120 cpt gr}{gs-10 pyrev{neg}ifp g cY 0 0 ro p OB/bL 120 sm dx -4.8 arc 25.8dp dv gr 0 pp}{ 8 fill dp g s st-1 e 90 CB pm cp ac 1.6 s t py 2 rot st}{Asc 3 0 ne{bW 0 2 rO DA}{dL dy mv l 0 xdvpp}{sqrtp l ln 16.8 dvm/w 12g 12 smo begin/version sm sc}b/Ov{ IngpAmvL/gs/gsave dp atro0 L/S{sflp ac l0 neg}if/pxcvOA}{1px st}{A wydv-2 dpneg}if/py rpy L/S{sf-1ptr/dy 10 mvOB rpx 16 0nparcsm div e1 a -1olpsmgs0 n/ex sgne{bW x00 l2m DLB -4.8 lWcw cmDA}{2.25steq{g 5 2cmspye05sl eclip}b/Ct{bs-.6 xlb1 sc gs-1 0 e neg CA 1lx w p16l1.5 4L o 1xdvexec}{al0 0 ro 8dpDA}{dL x/dx33600xpye x1elp e-1.6 gsomvsm py edpixmvpxgr1l145cv145 1elpyn/ey x 0m}b/dA{[3 S]}b/dL{dA ne{bW rO fill 8p2ps{dppataLdp3.375DLB 0a}ie}b/BW{wD wDrev{neg}if dp or{4SA gs sc0pxmv2.25L/xl/translatel}for g a}ie}b/BW{wDpxfillgr lysmeq{gs stl npp1np a}{exm dvlp1987,0bddpp 6 a}ie}b/WW{gs0rO1bWwxSA mbLpu cpHA}{dLCAneg bdend}b/Db{bs{dp type[]type n/dy0cWrOn o 12704.8sm pyCopyRighta}{ex12m-111scbsacaAp sc neg mv ac0.5eq{dp def/b{bind dpChemDrawpygr counttomark{bsg mScientific-1 beginsetgrayacpx st2 -80dplt{1mwFpxwx lpx0.3mL/ie/ifelsenpneg}if/pxL/l/linetogrcmcps0mgrdu st}b/OrA{py-1L/gs/gsave1.2lt{-1lt{-1 24.6 neg CAeq{dpdpnpmInc.psmpy -1py120bdclip}b/Ct{bssc0SA1.58ac 2.2cmDA}{dLDA}{cw l00sccmsm fill} RA}{61.2neggs50.3st}{0-1ac180 0 xl sqrt0.6 0.6 2sgdvlarc -11pcmclippat SAgDA}{cwl sc8neg}if/pyn0pxxpbWn/dxrx macacdpp 6-1.6dpnep0lgr}b/OB{ lmvgrCAHA}{dLrixpxnbdpradcmnp3OA}{1 dpLB2 fillsgsgsg023acsme127mv p 2 gr}{pp}{gs 0 a}b/PT{8gr1 p 1 -1 bd p cv chemdict ro 8 fill dv}{bd}ie py 11 cm 0 p 0 s 16 pp}ifels 0 n l gs sl WI

SISTEMA

D- L

MOLECULAS CON DOS O MAS CENTROS QUIRALES

Con tres centros quirales: Aldopentosas

D-eritrosa
CHO

D-treosa
CHO
CHO CHO

OH

HO

OH

HO

OH

OH

HO

HO

OH

OH

OH

OH

D-ribosa

CH2 OH

CH2 OH currentpoint currentpoint 192837465C H OH192837465 C H OH 19283746 currentpoint current

D-arabinosa

D-xilosa

D-lixosa

gr 165 2850 1186166I 746 4505 80 2589] ]d end164010 746 4010] chemdict begin 3218 4010 begin I 3626 2589 DSt [3 I 3 [1 [0881 420040754505]3182 2770 3182I3075] 2397 DSt [3 I 328 4010 DSt [4 I 74 /bs[[1 759 2487 DSt 40 1123 3075 DSt2397] 701 746759 2181 759 2487]96 40 DSt40 20 chemdict DSt [2 SP 638 4662 333 3825] 4720 2727 4591] 864 4641 1169 4010] 3961 3585 3775] 762 3520 762 3349] 4150 3145 5026] 742 3349 742 5075] 2589 3626 3961] 633 4770 328 3155] 2092 3218 4456] I 2669 /bs[[1 3182 100 80 4641] 2669] [1 gr [03218 3271 2732 [2 SP Db13349] 4613 3569 [1 I 1186 ]d 2669] 4591 3162 3271] [1 4662] 3470 2768 4613] end 20 3064 3344 3038 3264 3162 3073 3033 3280 3145 3321 I 2759 3649

SISTEMA

D- L

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MOLECULAS CON DOS O MAS CENTROS QUIRALES

Con cuatro centros quirales: Aldohexosas

D-ribosa
CHO CHO CHO H C OH HO C H H C

D-arabinosa
CHO OH HO C H

OH

OH

HO

HO

OH

OH

OH

OH

OH

OH

OH

OH

CH2 OH

D-alosa

CH2OH CH2 192837465 CH2 OH currentpoint 192837465 currentpointOH currentpoint 192837465 currentpoin

D-altrosa

D-glucosa

D-manosa

40 80 [1 1356 99 40 DSt40 20SP 2431 DSt [2 SP 5441 4477 DSt [4 I 5920 3995 DSt [ 50 5442 7842 3095 80begin7835 2460begin[3 I 022 3808] 2622 7422 2622] 034 3339] 3262 8298 3262] 858 5038] 4583 7396 4583] 458 3995] 4562 8219 4562] 030 4477] 3459 7819 3759] 874 2460] 4689 7406 4989] 044 2662] 3962 8282 3962] 920 161 5898 2790 7842I I 441end I 20 4127 7802 4428] chemdict DSt I 7802 4428 DSt [3 I 8282 3962 DSt [4 473[07835 2131 7835 2431]5473 8981 40 3155] 2662 DSt [23095] DSt 4611] chemdict [1 gr 7819 Db 7707 ]d 7981 [1 7802 /bs[[1 7842 70 4632] 7723 7998 7697 7918 I OB81SAradpynp1b10-80145fill0eq{DD}{DS}ie15gs2acOBsmseq{dpsetgray1210nHaplwbg5saRd0 ex12ChemDrawpx5atSA3600arcalradlt{-1fill0acocm0.5sleq{DB}{DS}iegst}{Asc360SSAdp/cw slfill1987,dv12ppylppl0e0gwx5slsl2.25ppac02.2x/dxslcmalpacwDstst144def/b{bindcpstZLB0.4pg/cr serwixpdict-.6radlt{-1fillrPrepDLB25.8tr/dysetgray2.251lro-2st}]epglp-1mvpxor{4est1end-1px2 s/gsavecmscDA}{cwgs00.6p1.2ac0pypxcppy-1smgi3dv/bdoginp[{py-1gsradfill}b/SA{aFmvDs 0pxndp-9.6mtepy-.62.25116aL0ne{bW1.5dv}{bd}iepgllWduppy0npcmg/wb0xwfillgr}ie}b/Cr{0 xg}if/pymvdpmv1986,31987,00.622.20px0lpfilldef/b{bindpxcXgr1bWgsWIcm1.5ac20cmpxmdv 16.8pscxexec}{alaAL/ix/indexCambridgecmDA}{dL Computing,1bspp}ifelse2gr120d/wF8ix p090CopyRightac0gr-1DLBpxdpst}{0 aAst}{AscacWIm2stmpOA}{1rOexlpsm0st}{pxlpxdv-1sc wyaR8aLsmexecL/gs/gsaveDA}{dLCADA}{cw05py02sxw4.8dp0DA}{270S}if/lp0ocpalraldef/ o gswxl1DA}{dLOA}{1cmmveydv/bd180dparcaclpp}ifelsecW1Sppsetdash}d/cR1giDA}{27 v %rPrep-9.6lp0cpt2scs24.6sqrt3dpwSAcvdx5bs00sc}b/Ov{OrAsetgrayscSApOA}{1.5parcgr} p}b/Ct{bspxwF0tr/dyscplscxnLBnegdvoOA}{1ppw0mwFSApAA}{1pp2s8atsc-0.4rrOacgi0nsccY s userdict/chemdictpynp -1pyrOerochemdictmv12dpcwbsDA}{cw0mvixmva/pxbd-14py1L/nA pL/gr/grestoregrL/xl/translateputsg -1pyscp027mvsmsgp-1116nemo50.5gr}b/OB{/bSap0pp nL/tr/transformlac02.2x/dxneg}if/px bsOA}{1lr-4.83gs1CB020gsrlinetomdivstbL-2xAc}{0.50s 1xlnpfill21msmbWmvne{bW02mtpcw -21lpyne dparcneglpcprO23aldpcmlW1L/mv/movetos-0. t}b/HA{lWputscmpxrotpydict0.5Computing,1Inc.2ac2700l mvaarcosmpgsglWdef}bind 18g -1lsg0.60pyscprochemdict begin/versiongra16epg/wb0ror{41lpsr1a/pyl0ac180-1grSA acpx 20.5 mvbWscxne{bW1.51 mn/dxarcpxmv1 dvnp[{pypxost}{0erOsgcp0.4wpxne0m/aLput-1-1cvCA t 0 dp/cYeynegdvcpo n/ex 1negcmCArOsg232 pxcY180004fillputmvpxp3dvpysmDA}{180 dvn m3.375gr}{pp}{gs 90-1 rad1201cptdpgr}{gs-1stcpppst}{pxendsc}b/Ov{OrA1r1ne{pyra 6,ro-1 r2dvbdm5parcn counttomark{bscXs180gr01clippath 4wygr39cYDT}]omst}]ea/pysc1 {1 2aclt{1py2pa}{ex12m type[]typefille-1.6bWx0eL/l/linetodvaccppx-0.43g/cX1xdv/bd r}if tpppy -2SA-1mv Laserpsc 4xsc-121.6sgbeginprgs0.627CA e2 rOwppdp0pxro4.8OA}{1ox}if l/translateWI1.2180 pySAgsgrsc2ace 0eq{dp sqrtpmt OA}{1.5lp sm01.6eq{gs mvLBlt{e}if 250bdend}b/Db{bs{dp ac e1801g xa}ie}b/WW{gs 6smx1 fill gsx}if1ZLBpgs3g/bbnpOA} py m2 1.2b2 e lpp 6 ac 1 n/ey scdvScientific1 SA al ac1 0 cplWpypo/cX xsetda lp dp L/ie/ifelse m}b/dA{[3 L/S{sf np cm rOLB st}{Asc radlWcm wx dup gsppcX 3 lW counttomark{bs16.8bd py1 0.5 L/ix/index lW e py L/mt/matrixro}ie}b/AA{npl r 145 gr xn 1 2 st}{Asc p DA}{cwnpm o x gr}b/OB{/bS cv pypp}{2AA}{1r -1 cp st}{0 s{dp -1 dx5 2 ac DA}{cw p npsgg px mv p cv dvst dv}{bd}ie 1802 xl}{xlg px gs m S]}b/dL{dAwx px 1 gr p cm px lx wx 4 e SA px s/wx s{nH d 9.6 r x 0 0l120 st np ac0.3 SA wF sm 8 00sc p at py lmdef}bind o 2 sl lp l gal gswpp1 w In pp}{sqrt at ex roa0 xm lW 1 0m}b/dA{[3pp}{2 -1.6 0 pymt 1 n 61 0 39 dp wy -1 a}b/PT{8dp 8 lp gi L/l/lineto16plp sm divL/mv/movetowb 41ix trfillgo lt{pp a a pA negm psm cp1 gr atpyl}for l 0 L/mt/matrix rev{neg}ifnpn proundgr}b/wDsmxs 5 gfill nm -1LBe 12pxaR8 -4.8rm 0 py wy0cp 16SApfill}b/SA{aF scscpp0 p lp21.62 py o -1ro 0eq{DD}{DS}ierogs8dp rev{neg}ifgssmveq{gs rwyly acat23exec0 L/n/neg scx e 1dv pxdvm/w xOBlst}{0 L/ie/ifelsescpg1lpx gsc CB16 grfill gr-116sm0w9.6 dxsggs ogr fill gr scg rO0mvOA}{1 end}b/Db{bs{dp type[]typep l ZLBlt{ppene{bWgifill aLp1 sm np cmsdp negg nxlgr}{gs 1mv n/dy-8SArlineto ne{bW bd 0 grmclippath scgrwcm wb cp 0.3-18 cmbdlstsl 3.375 -9.6OB CBpxslxmv4 -10cm2.2 cvfill SSA gr}b/In{pxdp S cpt 3L/m py 8OB/bLrotlnegst}b/HA{lW0 p16 x}if24.6-1s1.625.8 sgSA cmInc.2xlst}{1.03 lplWfillcm dp sc pm10 21.6neg}if/py m1rO0 2 sa}ie}b/BW{wD 1.5 025.8 e aclscmCA0rOdef}b/d/de -8py atHA}{dLbs8 0bW smo0CBeq{DB}{DS}ielpS]}b/dL{dA1o1r}if24.6bsxlcurrentmat st}b/OrA{pyCAaLwy180r -10ppybWxxlne{bWsmrnen/dy edppxpxOA}{1lcm 2lrad-1acemv -1cw 180pl}for clip}b/Ct{bsdy-1 lp 2cW3np begin/versionfill00 apgsm}b/CB{np[{[{CS} RA}{6DLBn/eygspylp ix sc12 rotrac 12rrotlcmbsn dy w 0.5 0grbs 27def/L{load4wy4em 2eq SAgr mv 0CA-9.6a}ie}b/BW{wDb1stDA}{2.25 rOpx 2 dvlbegindvdvcmBdAA}{1exec}b ln/ex m0rOL/S{sfa}ie}b/WW{gsl6begin6360arcscmv1bL DA}{2.25L/m/mul py1rOsetgra 2 p o p -1 dv Cambridge n DA}{dL SA p p n/dx e sm 2 m lp cpt cp a p ix dp180 p Scientificm/w mem ly neg}if/px x np -1 st ls 4 1 x mv neg bdx wD DLB gs 90 py dv/bd eq{dL}if 25.8gs dv m dv dp OB/bL 90 -.6 0 -1 cv m -1 p a neg 1 x}if begin e tr cm p g/bb xl}{xl sc gi p 27pp dv 0 mv 270 sm 4gr x 1

SISTEMA

D- L

MOLECULAS CON DOS O MAS CENTROS QUIRALES

Con cuatro centros quirales: Aldohexosas

D-xilosa
CHO CHO CHO

D-lixosa
CHO C H

OH

HO

OH

HO

OH

OH

HO

HO

HO

HO

HO

HO

OH

OH

OH

OH

C H 2OH

D-gulosa

currentpoint C H OH 192837465 C H OH currentpoin currentpoint OH C H 192837465 currentpoint 192837465

2

D-idosa

D-galactosa

D-talosa

SISTEMA

D- L

2303240 20 chemdict begin SP 24 2374] gr [0 I 2713 3266 DSt DbI 5630 2374 DSt [2 I 3212 3076 DSt [3 I 5630 31 0 4085 DSt [13 3212 2374 5 80 40 2374] 82 3240] 13 3266] 42 3791] 05 3765] 81 2564] 87 2538] 24 3115] 12 3076] 3212 DSt 4085] [1

mv1987,mpn/eylt{-1SA-150-10rCB16pxeq{dp27cmSA2OA}{1.50np2mv24.6 gsaplLBexec}b/CS msg0.3end}b/Db{bs{dppxxpygsrSA-11lgr0npdef/b{bindtrrO0rDA}{2701S}if/lpacs{nH2st}{0 25wxaLm1-121.6dpsne{bWLBL/l/linetonp[{py5stcmsstst}{pxpal1xr}if0sca/px26dvpx00p0mvr0 xill py10grpx21dv0xlescplpxpse30pyeq{DB}{DS}ielpslx1.5pl1rad439pgr}b/In{px1dxlpr59.6sgnfie 13.375DLBrotlbWlOA}{1mv12negl1pxx}iffillcpgsacg0fill}b/SA{aF0mL/m/mulrL/n/negalgr1xlD }b/HA{lWputac0pxpy360arc18010.5DA}{cwsc}b/Ov{OrAg/bbgo1xat2am/aLo/cXexsmcYdict B}if/pynxmtpro0aAst}{Ascx 2.25sge-2cW 23 pp-1clippathdef}bindesc ZLB pacOA}{1e-1scm 6.80.6p-9.6L/S{sf0npx/dx-10scdv/bds cXlparcrOpp}ifelseAA}{1ap0.5 round sc 1gsne{pyrOxn gs ixOB/bLmpcptstpy24.6sqrtrOp2.2sgsgpnesmg/wbmvbsstZLBcpt sdp execSA360 gis/wxAc} }b/Ct{bs0180-.6scgr}{gsarcdpw6SA xfillmvgrcY scl27pcppy10lWpp8xl4-0.4DA}{180aRw16. gsavenegcmpy1.5 rot16gs 1dycwwD epsallyppw1.6divlsm0gsgr0.4 x}ifst}{1.0xAc}{0.5rad p n/ex radpyDA}{cw050neggist}{0 filldv rlinetoene{bWst}]e1w-1 scDT}]oAA}{1 arcsc dvr s yaRscat0bdm/w180DLB 4 mvS]}b/dL{dA 1cmWI eq{gsSAac cm 3dv180 n-2321.6 dp/cYmp 90-1 dictdp00g 12 m m sm0.5 Computing,esm2ne270 lgist2rOsetgrayro}ie}b/AA{npdvsc0 rst}{00l1200b12-8 pylp begin/versionL/mt/matrix0sm e1dv/bd dv pxg/cXp def}b/d/def d pySAxDA}{dLpbsp 0p -1 sl 2 al acCA 0wy0bWatmpp}{2 2bd -1SA OA}{1 nH owbpy18ppDA l81gr scSArO CAxa}ie}b/WW{gs2 oxOA}{10 lgs 3 psm mv S gs -0.4 3 w gr}b/wD mv 120 counttomark{bs2.2cm r o acpp dvDA}{2.25smlWe fill1ppm sm}b/CB{np[{[{CS}{C lp dv 018scm sma}ie}b/BW{wDCBscrdpcmlbs 0cp 10dupdp end py sg 0 9.6 px rns1 n1.5 translate l}for 0 3n/dx 0.6 n/dy begindpn pcm04m 4al px setdash}d/cR xw p m 0dp 145 py e -1 m}b/dA{[3lWrev{neg}if o 0 2m or{4 wy a/py wb pplW0gr cmgs g/cYsm xr bd 1.2 -1 chemdict ac 0 1 lprO16 bs oInc.st}{Asc put px og py ix rO3 12 -1 L/np/n ,n ac dp x ac cp180 type[]typepy-1.61 px mt ro 4.8fill lt{ppwxCA xlcurrentmatrix 1bW L/ie/ifelse dx6 a0 r ac dp eq{DD}{DS}ie -4.8 25.8 cv0lx 1 mv 1 L/mv/movetocp 1 1 gr}ie}b/Cr{0dy 12ro ey radtr/dy g 2 neg}if/px xl}{xlp ac gr}b/OB{/bSdv px 4 fill g go 2 CA xpp ro px ne{bW 8 1 sc np Prep p mv L/ix/index OB 2 0 setgraypy sm py lgr ac def/L{load -1 lt{e}if 36 cv Cambridge Scientific mp npgr g pxw 0 25.8 x sc 0 cm sg cX cm 8 fill dv}{bd}ie wF begin ac 16 g DA}{dL 1 m cm0 90 2 0 wx gr gi cv l eq{dL}if aL d/wF bL cp p ix Bd rad -1 lW 1 0 lp pp 4 fill 3 l 1 -1

MOLECULAS CON DOS O MAS CENTROS QUIRALES

El nmero de ismeros es pus 2n siendo n el nmero de centros quirales

MESOCOMPUESTOS
COOH COOH H

OH

HO

OH

HO

La mitad de la molcula es imagen de la otra. No son quirales a pesar de contener centros quirales
currentpoint 192837465

COOH

COOH

Meso tartrico

El nmero de ismeros es 2n -1

SISTEMA

D- L

MOLECULAS CON DOS O MAS CENTROS QUIRALES

Tambin Mesocompuestos en anillos

A D D A

B currentpoint 192837465

B current

Si A = D y B = E El nmero de ismeros es 2n -1

SISTEMA

D- L

MOLECULAS CON DOS O MAS CENTROS QUIRALES

Tambin Mesocompuestos en anillos

A D A D

A D D

B E currentpoint 192837465 E E

currentpo

Si A = D y B = E No pticamente activo

SISTEMA

D- L

MOLECULAS CON DOS O MAS CENTROS QUIRALES

A veces no son mesocompuestos sino racmicos

X X
X X

currentpo

currentpoint 192837465

Anillo no plano = No existe plano de simetra

No es pticamente activo porque un enantimero se transforma en el otro a T ambiente

NOMENCLATURA DE ESTEREOISOMEROS - PROYECCION DE FISCHER - SISTEMA D -L -REGLAS DE CAHN-INGOLD-PRELOG - OTROS SISTEMAS DE DESIGNACION

-REGLAS DE CAHN-INGOLD-PRELOG
REGLAS DE PRIORIDAD

1) Los sustituyentes se ordenan en secuencia de nmero atmico decreciente del tomo directamente unido al centro quiral
H 4 I 1 Cl 3 1 H 4 CH3 3 2 NH2

2 Br

HO

-REGLAS DE CAHN-INGOLD-PRELOG
REGLAS DE PRIORIDAD

2) En caso de dos sustituyentes con igual nmero atmico del tomo directamente unido, tiene prioridad el que a su vez est unido a otro o a ms tomos de mayor nmero atmico y as sucesivamente.
4 CH3 2 CHCl2 CH2Cl 3 3 CH2-CH3 CH3 4 2 CH2CH2CH3

BrCH2 1

HOCH2 1

-REGLAS DE CAHN-INGOLD-PRELOG
REGLAS DE PRIORIDAD

3) Los enlaces dobles y triples cuentan como tantos otros sencillos.

2 CH=CH2 1 C=CH 3 CH2CH=CH2 1 COOH CHO 2 4 CH2CH2CH3

CH3CH2 4

HOCH2 3

-REGLAS DE CAHN-INGOLD-PRELOG
REGLAS DE PRIORIDAD

4) A todos los tomos excepto al hidrgeno y sus istopos se les asigna valencia cuatro y si su valencia es menor, se los considera unidos por las valencias que no tienen, a tomos que llamaremos fantasma y que se designan por un subndice cero. E tal forma que los tomos fantasma tienen nmero atmico cero y se correlacionan despus de cualquier tomo.
1 + -NHR2 2 -NR2

-REGLAS DE CAHN-INGOLD-PRELOG
Designacin R S

Una vez ordenados los grupos, se coloca la molcula de forma que el grupo correlacionado en ltimo lugar est lejos del observador y se sigue el orden de los otros tres grupos de mayor a menor prioridad.
1 4 2 3

-REGLAS DE CAHN-INGOLD-PRELOG
Designacin R S

Si el giro observado es a derechas como las manecillas del reloj. Se le designa R (del latn Rectus = derecho)
1 4 2 3

-REGLAS DE CAHN-INGOLD-PRELOG
Designacin R S

Si el giro observado es a izquierdas se le designa S (del latn Sinister = izquierdo)

1 4 3 2

-REGLAS DE CAHN-INGOLD-PRELOG
Designacin R S

En Proyeccin de Fischer si el grupo 4 est en la vertical el giro observado es el correcto pues se encuentra alejado de nuestra vista
4 2 1 4

1 3

Es S

-REGLAS DE CAHN-INGOLD-PRELOG
Designacin R S

En Proyeccin de Fischer si el grupo 4 est en la horizontal el giro observado es contrario pues el 4 se encuentra cerca de nuestra vista
2 2

1 3

Es R

422 3585 202374] I 3252 2374 DSt [1 I 5670 2374 DS 40 80 3252 chemdict begin SP 3 5145 3585] 4 6221 2564] 8 2727 2538] 6 3764 3115] 7 3252 3076] 5 5670 2374] gr [0 2005 40 DSt 4422
Designacin R S

mv20pxrnpaL-9.6l}foraACAHN-INGOLD-PRELOGcmslsm 1.62.251987,lpym0ac1.5ssc1650-1mvS]}b/dL{dA27cmne{bd OA}{1bW10eq{DD}{DS}ie mvs0st}{0begin23ppacWIgr}b c}{ex8npy radp0erosm-8gr}{gs01rOOBSApeq{dpo0w 0mtfill0 }{gsgsixfillnegputDExcp24.6pxarcdv/bdfill16ne1grpp}ifels epexmvwx dictpx210tr/dympg0type[]typexcXpaarclcmlpsmlw 2clip}b/Ct{bsdppcpt0xlnpcm sqrt180eq{DB}{DS}ie2327p pxpatn/ex sceypp 0g 008e0x/dx-4.80wFl6-2cW0mvrOl5 clippa4 daL16.8gr xDA}{dLacOA}{1 4p12dppp1oscrwyl0cpInc.ne270 L/gs/gsave0x120 ldv180py0pxarc0.5cw0.5DA}{cwmv21msm 1986,-REGLAS bWpxpyp-1 ace3acac2 rOsg rlineto eSA1Ob egst}b/HA{lWcmCAx scne{bWgidyp2.2 xl}{xlgrpbsgspp}{ arcn py-1 end}b/Db{bs{dp sm0.6 n/dymnp[{pygs mpx01 mOB900.6 nSArO py bsdv}{bd}ieal Computing,dppyst}{c rL/xl/translaterot b112rot360 xLBpywCBx}if fillpe-1 sccm e gslpfillPrepDLBL/S{sf0 SAnegs pyCBrev{neg}ifosmp divst tmv counttomark{bs2.2n/dxr x2r 25.8 cvdvs 11def/b{bind 80 sl l145 ppysc21.62a}ie}b/WW{gse -1ebegin 0cY cpeq{ Lneg}if/py 1.2 1800 stp 3Scientific rlp s xl-1.6wxsc}b/Ov{ LaseraRcv0m1n/ey l a}ie}b/BW{wD1 dvDA}{2.25 cmlW ldict lp SAat0mtm/w dp DLB rneg}if/px0 1 p np pxac 00ro n o acdv dp -1radlt{-1 1 lp gs sc 1 16 py gr 0bWat smor{ cpwy1 ac L/ie/ifelse py 180 -1 2.251 msg fillbs g/wb 0 s l5 1 12bd gr DA}{cw 6 sc begin/version lysmn g 2 p -13.375 1bdm -.6 dx g -1 gs oneg CA 0 lp ac 16 lp x pp st}{0 m x p st}{Asc 0L/l/lineto lx cm g mv np sg0.3 ne{bW L/ix/index lW px OA}{1 0 s L/ grm dp 8 mv m}b/dA{[32 sg2 0 np p 0 mv px Cambridge5 2 sl 0 ro sc 8 ro OB/bL -1 chemdict -1 m a l DA}{dL SA dp gs wD 0 90 px cm L/mt/matrix setgrayst 1.6

En este sistema de designacin en algunos casos, como el gliceraldehido monosacridos, coincide R con D y S con L
R=D
4
H CHO

CHO

S=L
H

OH

HO

CH2 OH

CH2 OH

currentp

-REGLAS DE CAHN-INGOLD-PRELOG
Designacin R S en Planos disimtricos perpendiculares

El eje de corte de los dos planos perpendiculares es el eje de referencia a lo largo del cual se va a observar la molcula para asignar la configuracin.
a
Br Cl H H

current

-REGLAS DE CAHN-INGOLD-PRELOG
Puede observarse desde a o desde b y supone considerar a la molcula como un tetraedro expandido.
Br Cl H
Br

06214 Designacin[1 9 8 7441Planos disimtricos DSt [3 I 3884 3145 4840] I 6719 57 I 6 3145 5129 DSt 20 6737 en 4353 DSt [2 I46 Ar /bs[[1 1 3145 2440 4371 DSt [4 nd 51314540 80 40 Ar chemdict begin SP 7225 4840 3145 5129] 3145 4895 6719 5111] 6719 3829 2440 3595] 2639 4371 3849 4371] 3668 4353 7225 4353] I S 4858 6737 4353 3849 4371 perpendiculares 103 3884 7441 3685] 4895 1676033 46 R 4389

}{6sm0wFstclip}b/Ct{bs0p0pyaAps1360begin/version0nepp-1mt27or{4stcppp-10.5L/m/mul21.60m p/cYm12pylL/gs/gsave-9.6180 008e0glp pxs10.5S]}b/dL{dAgr16scg270m1gsr44cv3sm}b/CB{np[{[{ wl2exec}{al02.25pyaLgrdprodvxOA}{1 sqrtst}{0CAeq{dp1obs2ne{bWrOput-1xgr}b/In{pxr314sglt{ grlt{1WI0negppgs gr radCambridgex/dxac12dpcwwDcXmvp0lg 0cp0stelpSAend 1x}ifst}{1.06xLBcX b/OrA{pygrLaserrPrepeypm/w 1.5rot16sme18016rO1-1.6bWgsclippathst2aclW setdash}d/cRL/n/n pA180nega}{exro-1 atxpy DA}{cw24.6 gsgi acn/dy00rgrfill27smpnelWbL225.8002sdpxlppfillDA}{18 m2dp -11.2gsatn/ex 1negput 0 bsdv}{bd}ielWComputing,dpac1mvL/mv/movetoat1809.6360gin 0-9.6xexec1986,145 x0eq{DD}{DS}ie 400.6wFeq{DB}{DS}iediv2cp AA}{1SAx-0.44CAnHcurren pp}{sqrt-9.6st}b/HA{lWrO0g 180m sc 5arcneg1SAlOA}{1o5 lpcmOA}{1.5px1eeq{dL}ifap-1er-1 W-2g-.6mvlcpofilln0.60dp -1-1 -.6pxpyScientific2pppx efill23 ldef/b{bind gil1gi 0.4pprad00-1gr}ie}b1 y/grestore1p5OB3.375DA}{dL 12m}b/dA{[390SAox}ifL/mt/matrixdupfillrOcptxdv2execxlscAc}{0 DA}{cwpataLsl 90ix scSAcmCAldpL/ix/indexal2.2beginagrrOpycm 11.5mvg/bbppy 24.6cmgrdvne{ 2rm HA}{dLpl16.8acend}b/Db{bs{dp -1-1 rOBlpdv sgs lysmcmsm l0p gr e0SS39osc DT}]oSAdxl12ga p mvscst scm wysg0.3nlL/ie/ifelsest}{Ascx0 dv/bdsDA}{cwInc.p3rost}{pxpxsetgrayro}ie}b/AA{ /transformarcnpy bdpDLB epcpt22.2cm type[]typepywy np 0ac 2px w4.8 dp1 lt{ppix01-0.4-2o/cXar rdict/chemdict counttomark{bsnp6 -1 rx sscCBrev{neg}if cm mp fill}b/SA{aF px lWBdp 0 aclppr9 p scmv npe ln 00lp SAdict rotbW -8 05 amv LB25.8 cv np[{pysc}b/Ov{OrAal0w -1r}ifsglpppx x cm x c pxdvCAbdL/xl/translatem 1b1 xl ne{bW mvp r2pxxl}{xlcpe cYgr}b/OB{/bSap mvround 2 g def} o mv sm mv 1 ac px 08scL/S{sfpyDLB neg}if/px-1 DA}{2.25 SAsm pydv/bd 8wxZLBn p OA}{ dvdv pyp p mv l8 dv 1.2 l}for stdx3p-1 -4.8 pysg px0nprlineto m x sm rad al cp py ix rO pxo ex ix ps{dp 5OA}{11987,0bdmac 0sc sc neg py0 w 6 sg16 larcpx est}{Ascbda/py m px4g/cX 3 wpy5 1 s dv negpxp p 12 cv py n/ey xcppy m 0 2 1ace -2 dv 1 1 at smpy st}]e cm lOA}{1 AA}{12d ill -1dp LBe neg}if/py 1mt x l p a}ie}b/WW{gsCB cW 0 w1.6 eq{gsl ZLB g dv 3a/px o -1 s opyRight np st}{0 ne{bW 0gr}{gs 2.25 12 m begin mv 0 bsdef}bind wbsclW gr}b/wD hemDraw exmv ro m1 21.6 a}ie}b/BW{wD1fill psetgray pp}{2 4grDA}{270 w ac gspxf mcm b2 2 rO a}b/PT{8gr-1 aRfill m 2 sm SAg gs o L/l/lineto0 bs st s 4 fill1p gs sc a 1 0 l g gr}{pp}{gs bW 120 chemdict r 0 gsl 0.5 dp wx 0 l tr wy gr ac def/L{loadx wb 0 lp np 2 mvwx 1 np m 1 dp p rad px 8 sc px mv OB/bL -1 lt{-1 n/dxsl dy mx lx cm g/wb p 0 1 m o S}if/lp s{n ac tr/dy 180 p 3 p 2 arc 0 lDA}{dL e sc cmp px rO 0 lp ac pp}ifelse p 0 WI sl 0 gs n np sc m/aL aL dv g 1 gs

H
Br

currentp

Cl Visto desde

Cl Visto desde

a
H H

currentpoint 192837

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gr end 51314540 80 40 20 ]d [02639 3829 2440 3595] [1 1 3668 4371 3849 4371] chemdict begin 4353 3849 4371 1 3145 3884 3145 4840] 31457 I 6 4353 7225 4353] 6737 4858 6737SP 394 6214 3145 5129 DSt [1 9 I 8 7441 4353 DSt [2 I46 Ar /bs[[1 DSt [3 I 2440 4371 DSt [4 I 6719 7225 3884 7441 3685] 3145 4840 3145 5129] 6719 4895 6719 5111] 103 4895 1676033 46 Ar 4389

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-REGLAS DE CAHN-INGOLD-PRELOG

Designacin R S en Planos disimtricos perpendiculares

Dada esa forma de ver la molcula se aplican las reglas de prioridad con la siguiente regla adicional: Los grupos unidos al centro ms prximo al observador tienen prioridad sobre los dems.
Br Br Cl Visto desde H H Cl Visto desde H

a
1
H

currentpoint 1928374

3 Visto desde

1 Visto desde

a
2 4

currentpoint 1928

NOMENCLATURA DE ESTEREOISOMEROS - PROYECCION DE FISCHER - SISTEMA D -L -REGLAS DE CAHN-INGOLD-PRELOG - OTROS SISTEMAS DE DESIGNACION

- OTROS SISTEMAS DE DESIGNACION

Zuckerman, Potapov, Terent y Kost

Se dibuja el compuesto en proyeccin de Fischer colocando verticalmente la cadena principal y una vez numerados los sustituyentes segn las normas y si el carbono quiral es el n y tiene un sustituyente X a la derecha se le designa sigma . Si est a la izquierda se le designa ro. n- sigma-X- (nombre del compuesto) n- ro-Y- (nombre del compuesto)

- OTROS SISTEMAS DE DESIGNACION

Zuckerman, Potapov, Terent y Kost

Ejemplo:
5 4 CH3 CH2 cido 3-sigma -bromo-3-metil-pentanoico cido 3-sigma -bromovalrico CH2 COOH cido 3-bromo-3 -ro -metil-pentanoico

3 CH3 -C- Br 2 1

ESTEROQUIMICA
Ha finalizado la
Cuarta y ltima PARTE

Muchas gracias por su atencin

Pedro Antonio Garca Ruiz
Catedrtico de Escuela Universitaria Area Qumica analtica Profesor Titular de Universidad Area Qumica Orgnica

Departamento de Qumica Orgsnica - Universidad de Murcia