,transcrib]'s ,note3 ,e ef=t has be5 made to replicate ?is text z fai?fully z possible4 ,"s *anges h be5 made4 ,!y are li/$ at ! end ( ! text4 ,syn!sis ( #b-me?yl-#d-sel5oqu9azolone1 #b-ph5ylb5zosel5azole1 & ,its ,d]ivatives4 ,,diss]tation ,,submitt$ ,,9 ,,p>tial ,,fulfillm5t ,,( ,,! ,,requirem5ts ,,= ,,! ,,degree ,,( ,,doctor ,,( ,,philosophy ,,9 ,,! ,,faculty ,,( ,,pure ,,sci5ce ,,( ,,columbia ,,univ]sity ,,by ,y-,,gwan ,,*51 ,m4 ,a4 ,,new ,,york ,,city #aibb ,,ackn[l$gm5t ,,& ,,d$ication ,! foll[+ rese>* 0 und]tak5 at ! sugge/ion ( ,pr(essor ,m>/on ,taylor ,bog]t to ^: int]e/ & advice ?is "w owes :atev] m]it x may possess4 ,y4 ,g4 ,,*54 ,,cont5ts ,ackn[l$gm5t & ,d$ication #b ,ab/ract ( ! ,diss]tation #d ,purpose ( ! ,rese>* #e ,introduction #g ,ph>macological ,review #h ,t9ctorial ,review #ad ,exp]im5tal3 #af #b-me?yl-#d-sel5oqu9azolone ,f\r ,me?ods ( ,prep>ation ,analysis ( ,sel5ium ,organic ,comp\nds #b-ph5ylb5zosel5azole ,mononitro ,d]ivative ,monoam9o ,d]ivative ,monoacetyl ,d]ivative ,monob5zylid5e ,d]ivative ,an ,azo ,dye ,d9itro ,d]ivative ,diam9o ,d]ivative ,diacetyl & ,dib5zylid5e ,d]ivatives ,dye+ ) ,azo ,dyes ,bibliography #be ,vita #bh ,,ab/ract ,,( ,,! ,,diss]tation #a4 ,:at 0 attempt$8 ,attempt 0 made to /udy organic sel5ium comp\nds ( ! het]ocyclic s]ies 9 ref]5ce to ^? prop]ties lead+ to t9ctorial & ph>maceutical possibilities4 #b4 ,:at 7 ! me?ods ( attack8 7a7 ,organic sel5ium comp\nds 7 review$ & _! prop]ties exam9$ critically ) ^? ( alli$ comp\nds4 7b7 ,"s new het]ocyclic comp\nds ( sel5ium 7 /udi$ & _! *>act]i/ic prop]ties m closely exam9$ along ! desir$ l9e4 #c4 ,9 h[ f> 7 ! attempts successful8 ,! lit]ature 0 review$ & classifi$ ) ref]5ce to ! prop]ties "u consid]ation1 & new sel5ium organic comp\nds 7 prep>$ & /udi$ :i* x is hop$ may ?r[ "s additional light ^u ! problem4 #d4 ,:at contribution actually new to ! sci5ce ( *emi/ry has be5 made8 7a7 ,comp\nds newly made h be5 %[n to exhibit a di/9ct t9ctorial value 9 comp>ison ) _! analogues4 7b7 ,!y h be5 %[n to be *emically easi] to h&le ?an ! correspond+ sulphur comp\nds4 7c7 ,sel5ium1 9 ! nucleus ( cyclic comp\nds1 has be5 %[n to be in/rum5tal = a positive coloration at lea/ equal to ! --,,nh-- or --,s-- gr\p+s4 ,! sel5oc>bonyl1 3,c3,se1 has be5 %[n to be a m p[]ful *romophore ?an ?ioc>bonyl1 3,c3,s1 or c>bonyl itself1 3,c3,o4 7d7 ,two s]ies ( azo dyes ( sel5ium h be5 prep>$ & h be5 %[n to possess a m>k$ t9ctorial value4 7e7 ,! foll[+ new comp\nds h be5 prep>$3 #b-me?yl-#d-sel5oqu9azolone #b-ph5ylb5zosel5azole,a #f-nitro-#b-ph5ylb5zosel5azole #f-;am9o-#b-ph5ylb5zosel5azole #f-;acetylam9o-#b-ph5ylb5zosel5azole #f-;b5zylid5eam9o-#b-ph5ylb5zosel5azole 7,b-naph?yl7-#f-;azo-7#b-ph5ylb5zosel5az ole7 ,d9itro-#b-ph5ylb5zosel5azole ,diam9o-#b-ph5ylb5zosel5azole ,diacetyldiam9o-#b-ph5ylb5zosel5azole ,dib5zylid5$iam9o-#b-ph5ylb5zosel5azole ,,purpose ,,( ,,! ,,rese>* ,s9ce ,b]zelius publi%$ ! fir/ resume ( ! *emi/ry ( sel5ium1 9 #ahah7a71 _m articles h appe>$ 9 ?is field4 ,sev]al reviews7#b7 ( its comp\nds1 includ+ ref]5ces1 h be5 publi%$1 besides ! resumes 9 ! *emical diction>ies4 ,^! reviews are conf9$ ma9ly to ! inorganic side4 ,no attempt has ev] be5 made to compile a bibliography ( sel5ium organic comp\nds4 ,f "t to "t1 articles h appe>$1 b ! field is /ill a promis+ "o1 ) _m allur+ possibilities4 ,9 ! p]usal ( ! organic records ( ! metal1 di/ribut$ ov] ! span ( a c5tury1 !re are indications ( ! value ( sel5ium comp\nds = ph>maceutical & t9ctorial uses4 ,an ef=t has be5 made to collect ^! scatt]$ data = critical exam9ation ) o!r analogues & sulphur comp\nds 9 p>ticul>1 & to prep>e & /udy "s new organic comp\nds conta9+ sel5ium1 = ! purpose ( ga9+ additional light ^u ! *emi/ry ( su* sub/ances1 & 9 ! hope ( discov]+ "s :i* may be ( practical s]vice 9 m$ic9e or else:]e4 ,syn!sis ( #b-me?yl-#d-sel5oqu9alozone1 #b-ph5ylb5zosel5azole & ,its ,d]ivatives ,,introduction ,! g5]al conception ( sel5ium is t x is a comp>atively r>e elem5t4 ,few realize t x has be5 kn[n = ov] a c5tury & t ov] tw5ty sel5ium m9]als1 conta9+ f "o to sixty-six p] c5t4 ( ! metal1 are consid]$ by ! m9+ corporations z important4 ,beside be+ a by-product ( sulphuric acid manufacture1 x is sep>at$ also 9 ! electrolytic ref9+ ( copp]4 ,! dem& = ! metal is s small t !re are half a doz5 conc]ns 9 ! ,unit$ ,/ates ei!r will+ to supply gratis any reasonable quantity = rese>* "w1 or to sell x at co/4 ,9 a special report ( ! ,national ,rese>* ,c\ncil on sel5ium7#c71 x is e/imat$ t !re c\ld be produc$ annually1 )\t mak+ any mat]ial additions to ! pres5t plants1 n less ?an #cjj1jjj p\nds4 ,9 fact sel5ium has1 9 rec5t ye>s1 gradually be5 br\ght m & m to ! att5tion ( ! g5]al public ?r\gh its application to milit>y uses & o!r purposes4 ,9 ! glass indu/ry1 = example1 x 0 us$ z decoloriz] dur+ ! ,w> p]iod4 ,x has be5 f\nd t x imp>ts a violet r$ t9t to ! pyrex tub+ aft] ! latt] has be5 us$ = a few combu/ions4 ,! coloration is especially noticeable :5 a brok5 piece is exam9$4 ,?is may f9d an important place 9 ! c]amic indu/ry4 ,9 turn+ (f ! gas light ( ! city at day break1 9 controll+ ! draft ( ! factory *imneys1 & 9 regulat+ ! rapidity ( ! manufacture ( sulphuric acid1 ! sel5ium cell is an important labor sav+ factor4 ,9 a simil> way x is us$ 9 automatically light+ & ext+ui%+ light buoys4 ,x also f9ds application 9 photometry1 wireless telephony1 milit>y telegraphy1 & army signal+ z well z = ! transmission ( signatures1 h&writ+s1 f+] pr9ts1 & images 9 g5]al7#c77d74 ,! "q ( ! vulcanization ( rubb] also %\ld be consid]$4 ,"s exp]im5ts h be5 publi%$ claim+ ! simil>ity ( ! action ( sel5ium & sulphur on rubb]7#d77e74 ,! co/ ne$ n be prohibitive1 s9ce ! supply c\ld be easily increas$ & ! price r$uc$ provid$ !re 7 a dem&4 ,9 ! p]sonal exp]i5ce ( ! writ]1 :5 work+ ) ! hydrog5 sel5ide gas1 ! rubb] connections ( ! app>atus soon turn$ r$1 & aft] a few h\rs 7 s cle> a r$ t visitors to ! laboratory imag9$ t ! writ] 0 us+ ! ord9>y r$ rubb] connections4 ,! rubb] ?us *ang$ seems to be s(t] & m ela/ic ?an ! orig9al2 ?is obs]vation w be foll[$ up4 ,9 ?is c\ntry ! ,national ,rese>* ,c\ncil has creat$ a special committee ( sev5 to inve/igate ! v>i\s possible uses ( sel5ium & tellurium4 ,,ph>macological ,,review ,duhamel & ,rebi]e7#f77g7 %[$ t an injection ( a trace ( r$ colloidal sel5ium into rabbits increas$ urea excretion regul>ly4 ,9 o!r cases satisfactory results 7 claim$ & ! liv] %[$ "s lesions4 ,! hi/ological modifications produc$ by injections into rabbits are mo/ app>5t 9 ! liv] & kidneys4 ,9 ! di/ribution ( colloidal prep>ations 9 ! animal body by injection1 ,duhamel & ,juill>d7#h7 f\nd t ! liv] conta9$ ! greate/ am\nt4 ,six ye>s lat] ! =m]7#i7 us$ a simil> prep>ation introduc$ into ! animal intrav5\sly1 & sel5ium 0 aga9 f\nd 9 ! liv]1 al?\gh 9 small] quantity4 ,sulphur comp\nds h simil> physiological action4 ,x is kn[n t triph5yl/ib9e sulphide1 or sulph(orm1 7,c,h7,sb,s1 has a curative effect 9 sk9 diseases1 z x lib]ates 8nasc5t0 sulphur on ! sk94 ,x is equally natural to expect "s organic sel5ium comp\nd :i* lib]ates f9ely divid$ sel5ium to ex]t a rem$ial influ5ce on animal bodies4 ,! sel5oqu9azolone prep>$ 9 ! c\rse ( ?is rese>* & describ$ m fully 9 ano!r section ( ! pap]1 has ?is prospect4 ,! qu9azolone has ! foll[+ /ructure3 ,n _/ _/ ,c-,,* ,,nh _/ _/ ,c ,se ,exp]im5ts 7 c>ri$ on at ,l',in/itut ,pa/eur 9 ,p>is "u ! sup]vision ( ,m4 ,borel = ! treatm5t ( canc] 9 mice4 ,no human subjects 7 exp]im5t$ ^u1 al?\gh results 7 claim$ by us+ sel5ides & _! oxidiz$ salts4 ,sel5ium dyes 7 f\nd to be m$ic9als1 al?\gh no relation has yet be5 e/abli%$ betwe5 con/itution ( ^! organic dyes & _! !rapeutic value4 ,wass]mann7#aj7 made sev]al eos9 prep>ations1 by c\pl+ ! sodium d]ivative ) potassium sel5ocyanide4 ,! r$ dye/uff ?us prep>$ is /at$ to be easily soluble 9 wat]4 ,wass]mann1 ,keyss] & ,wass]mann7#aa7 made exp]im5ts ) x1 *emo!rapeutically1 on animal tumors4 ,:5 ! solution 0 inject$ into mice tumors ! latt] turn$ r$1 accompani$ by ! s(t5+ ( ! tumor aft] ! ?ird injection & complete resorption aft] t5 injections1 unless ! dose us$ 0 too great = ! animal4 ,9 t case dea? (t5 occurr$4 ,good results 7 also report$1 9 connection ) ?is exp]im5t1 on f\r diff]5t /ra9s ( m\se c>c9oma & "o /ra9 ( m\se s>coma4 ,9 ! latt] case1 relief 0 f\nd soon] b ! =m] disappe>$ m sl[ly4 ,ano!r prep>ation 0 made lat]7#ab7 & introduc$ into mice intrav5\sly & aga9 f\nd to h good results4 ,! foll[+ is ! /ructure ( #b-sel5ocyanidean?raqu9one-- ,o ,c ,se,c,n _/ _/ _/ _/ _/ _/ _/ ,c ,o :i* has also be5 report$ to h m$ic9al uses7#ac74 ,p4 ,ehrli* & ,hugo ,bau]7#ad7 syn!siz$ f p4p-diam9o-diph5yl- me?ane ! r$ dye #c1f-;diam9osel5opyron9e4 ,,* _/ _/ _/ ,h,n ,,nh _/ _/_/ _/ ,se ,! dye has be5 us$ ^u mice & caus$ pron\nc$ edema4 ,! toxicity ( bo? ! sel5opyron9e & ! correspond+ sulphur comp\nd 0 comp>$ "u simil> conditions 9 ! same exp]im5t1 & x 0 f\nd t ! sel5ium dye 0 toxic 9 #a_/cjjj gram1 b ! sulphur dye 0 toxic 9 #a_/bejj gram p] tw5ty gram weight ( ! animal4 ,?is physiological activity 0 not$ ye>s ago ) ! inorganic comp\nds ( sel5ium & ,b]zelius7#ae7 describ$ ! poison\s effect ( hydrog5 sel5ide q impressively2 8,9 ord] to get acqua9t$ ) ! smell ( ?is gas ,i all[$ a bubble n l>g] ?an a pea to pass into my no/ril2 9 consequ5ce ( its smell ,i s completely lo/ my s5se ( smell = sev]al h\rs t ,i c\ld n di/+ui% ! odor ( /rong ammonia ev5 :5 held "u my nose4 ,my s5se ( smell return$ aft] five or six h\rs1 b sev]e irritation ( ! muc\s membrane set 9 & p]si/$ = a =tnight40 ,! writ] has be5 work+ on ! gas = "s "t & 0 also q s]i\sly affect$ once1 ! injury p]si/+ = _m days4 ,t x is m poison\s ?an ! hydrog5 sulphide is well kn[n4 ,bru]e7#af7 %[$ t :5 hydrog5 sulphide 0 pass$ into blood solution sulphemoglob9 0 produc$ 9 consid]able quantity1 due to ! *emical action ( sulphur & hemat94 ,he /at$ fur!r t sulphemoglob9 may be f\nd 9 animal blood :5 a l>ge am\nt ( ! gas has be5 inhal$4 ,he made sel5hemoglob9 9 ! same mann]4 ,sixte5 ye>s lat]1 ,cl>ke & ,hurtley also prov$ t sel5hemoglob9 may be made by pass+ hydrog5 sel5ide into blood7#ag74 ,^! exp]im5ts may be int]pret$ to mean t ! oxy-hemoglob9 is trans=m$ into an organic complex ( sulphur or sel5ium1 & t ! transf]5ce may be m rapid & p[]ful 9 ! case ( hydrog5 sel5ide4 ,biological inve/igations h suffici5tly prov$ t dye/uffs ( ! ph5az9e1 oxaz9e1 ?iaz9e1 acrid9e s]ies %[ an injuri\s effect on protozoa1 especially ^? dyes conta9+ sub/itut$ am9o gr\p+s & ( a simple /ructure7#ah74 ,9 ! case ( ! ?iaz9e dyes ( ! me?yl5e blue class1 ! physiological importance has well recogniz$ 9 _! use z feeble antiseptics & analgesics4 ,ehrli* & ,guttmann7#ai7 initiat$ ! use ( me?yl5e blue z an antip]iodic & its use 9 t l9e has be5 cont9u$4 ,9 ! field ( ! sel5az9e dyes1 ph>macologi/s h n yet paid mu* att5tion to !m1 on acc\nt ( ! newness ( ! discov]y1 b ,p4 ,k>r] claims t !y are indisputably 8vital dye/uffs07#bj74 ,! prospect ( syn!siz+ sel5az9e dyes & _! use z drugs seems to be bright1 judg+ f ! fact t !y are easily prep>$ & capable ( _m comb9ations1 especially ( ! ease ) :i* !y =m organic complexes ) ars5ic comp\nds4 ,,no ,,nh ,,no ,,nh ,,no 7,i7 _/ _/ _/ _/ _/ _/ _/ _/ ,,nh ,cl ,se,h ,,nc ,,no ,se,h ,,no ,,no _/ _/ _/ _/ _/ _/ _/ _/ ,o,n ,se ,=mula 7,i7 is kn[n1 z #a1 #c-;d9itrob5zosel5az9e7#ba71 :i* 0 obta9$ by ! action ( picryl *loride on ! z9c salt ( o-am9osel5oph5ol2 ! product 7picrylam9osel5oph5ol7 be+ !n treat$ ) alkali & ?us conv]t$ to ! dye1 :i* ^u exp]im5tation %[$ m>k$ effects ^u protozoa & bact]ia4 ,n _/ _/ _/ ,n ,,nh _/ _/_/ _/ 7,,ii7 _/ _/ _/ _/ ,se _/ _/ _/ ,cl _/ ,se ,,ho,z ,,nh _/ _/ ,,ho,z ,=mula 7,,ii71 kn[n z #c-7p-ph5yl>sonic7-am9osel5az9e1 is r$ 9 dilute alkali & gre5 9 m9]al acid1 & is a typical dye 9 a s]ies f ! c\pl+ ( sel5odiph5ylam9e ) ars5ic comp\nds4 ,all possess simil> toxicity z ! ?iaz9e dyes7#bj74 ,o!r sel5az9es are li/$ 9 ! bibliography7#bb74 ,no less ?an half doz5 ?i\reas are commonly us$ z drugs4 ,?i\rea itself p>alyzes ! n]ve c5t]s1 & is employ$ comm]cially = photograph fix+ & = remov+ /a9s f negatives2 ?iuret1 ,c,h,n,s1 s]ves z a sub/itute = iod(orm2 ?ios9am9e-e?yliodide1 or tiod9e1 ,,ih,c,h,,ncsnhc,h1 is us$ = relief ( lesions ( ! c5tral n]v\s sy/em2 allyl?i\rea or ?ios9am9e1 7,,nh7,,sc4,,nh*,,*3,,*1 = aid+ ! absorption ( connective tissues1 = treatm5t ( burns1 keloids1 ure?ral diseases1 scl]otic conditions ( ! e>7#bc74 ,sel5oc>bamide & a numb] ( its d]ivatives h be5 prep>$ & /udi$4 ,"o class ( sel5o ureas has be5 pat5t$ z ph>maceutical products by ,*em4 ,fabrik von ,heyd57#bd71 & are prep>$ by ! action ( hydrog5 sel5ide on alkylcyanamides1 ,,rnh4,,*n ,h,se ,,rnh4,c,se4,,nh ,!y possess pron\nc$ !rapeutic value &1 s]ve z int]m$iate products 9 ! production ( m /able alkyl halide additive comp\nds4 ,o!r c>bamides rang+ f sel5o urea itself7#be71 7,,iii7 & a cyclic urea7#bf7 7,,iv7 are describ$ 9 ! lit]ature3 ,,nh ,,*-,se _/ ,se3,c 7,,iii7 ,c3,,nh 7,,iv7 _/ ,,nh ,,*-,,nh ,! latt]1 kn[n z e?yl5e-sel5\rea1 may be classifi$ also 9 ! azole gr\p z #b-;im9otetrahydrosel5azole 7,v74 ,h,c----,,nh 7,v7 ,h,c ,c3,,nh _/ ,se ,! lit]ature = ! o!r normal c>bamides is li/$ 9 ! bibliography7#bg74 ,sel5oantipyr9es1 sel5osac*>9e1 sel5o9digoes h also be5 prep>$4 ,?ioph5e & its d]ivatives are ( consid]able !rapeutic int]e/4 ,?ioph5e itself is f\nd to be useful 9 less5+ ! elim9ation ( sulphuric acid 9 ur9e1 & is employ$ 9 ! d]matological practice4 ,sodium ?ioph5e sulphonate1 ?ioph5etetra-bromide1 ?ioph5e diiodide1 are all m$ic9als7#bc74 ,a numb] ( sel5oph5es are record$ 9 ! lit]ature4 ,_! relation to ! sel5azoles may be easily se5 f ! foll[+ =mulas3 ,,*--,,* ,,*--,n ,,* ,,* ,,* ,,* _/ _/ ,se ,se ,sel5oph5e ,sel5azole ,dime?yl sel5oph5e 0 prep>$ f acetonyl acetone & phosphor\s p5tasel5ide1 ,,* ,,* _/ _/ ,,hc,c ,,hc,c ,,oh ,p,se ,se ,,oh _/ _/ ,,hc,c ,,hc,c ,,* ,,* ,! comp\nd ?us obta9$ is /at$ to h ! same odor z ?ioph5e1 b no m5tion is made 9 reg>d to its uses7#bh74 ,sel5oph5e 0 prep>$ f sodium succ9ate & phosphor\s trisel5ide1 or by conduct+ e?ylsel5ide ?r\gh hot tubes7#bi74 ,"s sel5azoles f9d application also 9 m$ic9e4 ,at pres5t only ! isoazoles are kn[n to h physiological uses4 ,"o ( !m 0 prep>$ f an?raqu9one sel5ocyanide1 by ! action ( ammonia "u pressure7#cj74 ,,nh,h ,n-,se ,o ,c ,se,c,n ,c _/ _/ _/ _/ _/ _/ ,,hcn ,h,o _/ _/ _/ _/ _/ _/ ,c ,c ,o ,o ,ano!r type ( azoles1 b5zosel5diazole 7piasel5ol7 & five ( its d]ivatives1 h be5 also describ$ z m$ic9als7#ca74 ,! diazole itself has ! foll[+ /ructure1 ,n ,n _/_/ _/ _/_/ _/ ,se or ,se _/ _/ _/ _/ ,n ,n ,diazoles ( ! foll[+ /ructure are also kn[n1 b no data 7 f\nd1 reg>d+ _! physiological action7#cb73 ,n-,n ,n-,n _/ _/_/ ,,*,c ,,c* ,c,h,c ,,cc,h _/ _/ ,se ,se ,dime?yl-sel5o-diazole ,diph5yl-sel5o-diazole ,sulphides & disulphides h curative p[]4 ,dime?ylsulphide is us$ = int]nal treatm5t1 di-o-am9oph5yldisulphide is us$ = intramuscul> injections4 ,diallyl sulphide is also a m$icam5t4 ,me?yl sel5ide has "s effect on ! int]nal p>ts ( ! body7#cc74 ,hanzlik & ,t>r7#cd7 at ! ,am]ican ,univ]sity ,exp]im5tal ,/ation1 %[$ t a numb] ( sel5ium comp\nds act z sk9 irritants3 e4g41 di*lorodie?yl sel5ide1 di*lorov9yl sel5ide1 tri*lorodie?yl sel5ide & sel5ium mu/>d oil4 ,! fir/ m5tion$ prov$ z pot5t z ! sulphide1 b ! o!rs fell some:at bel[ 9 _! effects4 ,diantipyryl sel5ide is ano!r !rapeutical ag5t7#ce74 ,! disel5ides occupy an important place ( _! own4 ,! sel5oph5ols d n rema9 un*ang$ 9 ! air1 b are always oxidiz$ to ! disel5ides1 :i* c be aga9 r$uc$ to ! sel5oph5ols4 ,s f> only ! disel5ides ( an?raqu9one & _! ph5ols are recogniz$ rem$ies7#cf74 ,,t9ctorial ,,review ,_m ( ! sel5o organic comp\nds are color$1 :ile ! correspond+ sulphur d]ivatives are colorless4 ,,hc-,,* ,,hc-,,* ,,hc ,,* ,,hc ,,* _/ _/ ,o ,s ,furane1 colorless ,?ioph5e1 colorless liquid liquid ,,hc--,,* ,,hc--,,* ,,hc ,,* ,,hc ,,* _/ _/ ,,nh ,se ,pyrrol1 colorless liq4 ,sel5oph5e1 yell[ liq4 b turns br[ni% 9 air aft] repeat$ extraction,b ,?is br+s sel5oph5e m ak9 to pyrrole ?an ?ioph5e1 b ! gr\p -,,nh- 9 ! molecule ( pyrrole is an auxo*rome4 ,! sel5ium atom 9 a cyclic comp\nd also acts l an auxo*rome4 ,sel5oantipyr9e7#cg71 ,c,h ,n _/ ,,*,n ,c,se ,,*,c,,* =ms pure yell[ cry/als f alcohol1 :ile ! correspond+ comp\nds ( oxyg5 & sulphur are colorless4 ,simil>ly1 ! #b-me?yl-#d-sel5oqu9azolone is deep br[n 9 color1 :ile ! ?io comp\nd1 prep>$ by ,bog]t & ,h&7#ch7 is light br[n or yell[ & ! correspond+ oxyg5 comp\nd is colorless or ne>ly s4 ,die?yl sel5ide 7,c,h7,se1 is a yell[i% heavy oil ( unpleasant odor4 ,x comb9es readily ) *lor9e to =m a *loride 7,c,h7,se,cl1 & ! latt] is oxidiz$ by nitric acid to =m an oxide 7,c,h7,se,o17#ci74 ,die?yl sulphide is a colorless syrupy liquid1 z well z die?yl am9e & die?yl e!r4 ,! gradation ( color is q pron\nc$ 9 ! case ( sel5onaph!ne qu9one7#dj74 ,,co ,,co ,,co ,,co _/ _/ _/ _/ _/ _/ _/ _/ ,,co ,,co ,,co ,,co _/ _/ _/ _/ _/ _/ _/ _/ ,o ,s ,,nh ,se ,x w\ld be mo/ natural to conclude t ! *romophore 3,,cs is m p[]ful ?an 3,,co1 & t 3,c,se is mo/ p[]ful ( all1 z %[n 9 our /udy ( qu9azol9e comp\nds4 ,x w\ld equally foll[ t 3,s is a m p[]ful color-=m+ radical 9 a cyclic comp\nd ?an t ( 3,o2 & 3,,nh ?an t ( 3,s2 & 3,se aga9 mo/ p[]ful ( ! :ole s]ies4 ,less] & ,weiss7#da7 9 _! rese>* on sel5o9digo /at$ t ! sel5ium dye/uff1 on acc\nt ( its great] molecul> weight ?an sulphur1 %[s a deep] blue4 ,?is hypo!sis meets a difficulty 9 ! case ( c\mor&ione1 ?ionaph!nequ9one & isat9 s]ies1 :]e ! -,,nh- radical has an atomic weight ( #ae1 & -,s- #cb1 & %[$ ! rev]s$ ord] ( color4 ,?is seems to be ! case 9 ! sel5oph5e s]ies also4 ,!re=e ?is !ory is n )\t exceptions4 ,! disel5ides pres5t a v int]e/+ /udy also4 ,me?yl disulphide is colorless1 b me?yldisel5ide7#db7 is a r$di% yell[ liquid4 ,me?yl disulphide only becomes yell[ :5 x is treat$ ) *lor9e1 & 9 su* cases 7,,*7,s,cl is =m$7#dc71 9 yell[ rhombic cry/als4 ,e?yldisulphide is colorless3 e?yl- disulphid$i*loride is a fa9t yell[ oil7#dd74 ,b ! correspond+ e?yldisel5ide is a r$ liquid7#de74 ,ph5yl disulphide is colorless1 & ph5yldisulphide dibromide is ( "m-(-pe>l appe>ance1 & practically colorless7#df71 :ile ph5yl disel5ide =ms pure yell[ ne$les7#dg71 & ph5yldisel5ide dibromide orange r$ ones4 ,:ile ph5yldisulphide is colorless1 :5 an auxo*rome gr\p is add$1 su* z ,,nh1 ! comp\nd is color$4 ,?is is ! case ) o-diam9odiph5yldisulphide7#dh7 :i* is yell[ bo? 9 solution & 9 cry/all9e =m4 ,9 o!r words1 an auxo*rome 9 addition to ! *romophore gr\p trans=ms a colorless *romog5 into a color$ "o4 ,!re=e gr\ps l -,s4,s- & -,se4,se- are *romophores 9 ! same s5se z -,n3,n-4 ,?is is 9 agreem5t ) ! *romophore ideas ( ,hugo ,kaufmann4 ,! -,se4,se- is a m p[]ful *romophore ?an -,s4,s-4 ,?is br+s "o directly to ! inquiry z to :y #b-ph5ylb5zo- sel5azole1 :i* conta9s a 3,se radical1 %\ld be colorless2 & t ev5 #f-nitro-#b-ph5ylsel5azole1 ) ! addition ( a *romophore ,,no1 %\ld be only fa9tly color$4 ,! b5zo?iazoles1 _! isom]s & d]ivatives are mo/ly colorless1 & simil> causes are probably responsible 9 ! case ( ! ph5ylb5zosel5azole1 = its lack ( color4 ,b :5 ?is sel5azole is comb9$ ) ano!r *romophore1 = example an azome?9e gr\p+1 ! result is a m positively color$ comp\nd 79 ?is case b5zalam9osel5azole71 ! cry/als be+ yell[4 ,! correspond+ ?iazole d]ivative is light color$4 ,! t9ctorial value ( ! sel5ium d]ivative is fur!r evid5c$ by ! ease ) :i* x =ms azo dyes & ! deep colors ( ! latt]4 ,?is 0 obs]v$ :5 #f-;am9o-#b-ph5ylb5zosel5azole 0 diazotiz$ & c\pl$ ) ,b-naph?ol1 salicylic acid1 etc4 ,! correspond+ am9o?iazole has be5 consid]$ difficult to diazotize1 on acc\nt ( its insolubility 9 hydro*loric acid1 cold or hot1 b ! am9osel5azole dissolves readily & completely1 ! c\pl+ is almo/ in/antane\s1 & ! dyes obta9$ are mo/ly r$ & ( metallic lu/re4 ,9 view ( ! /ability ( b5zosel5azoles t[>d hot conc5trat$ acids 7) ! exception ( nitric1 :5 nitration ensues7 & alkalis1 ^! dyes may prove ( "s comm]cial int]e/4 ,! azole dyes ( ! b5zosel5azole h be5 expos$ to light = weeks1 & also expos$ to acids & alkalis1 & h be5 f\nd to be q fa/4 ,,exp]im5tal ,prep>ation ( #b-me?yl-#d-sel5oqu9azolone ,bus* prep>$ qu9azol9es by ! action ( o-am9o or o-nitro b5zylam9e ) phosg5e1 & ?ioqu9azol9es ) c>bon disulphide7#ea73 ,,*,,nh ,,*-,,nh _/ _/ ,c,h ,c,o,cl ,c,h #b;,h,cl ,,nh ,,nh--,,co ,,*,,nhc,h ,,*-,,nc,h _/ _/ ,c,h ,,cs ,c,h ,h,s ,,nh ,,nh--,,cs ,accord+ly ! same reaction 0 tri$ ) o-nitrob5zylam9e1 prep>$ by ! me?od ( ,lellmann & ,/ickel7#ej71 us+ c>bon disel5ide7#ea74 ,! reaction seem$ to "w1 b ! mixture =m$ 0 difficult to extract & x appe>$ t o!r reactions took place at ! same "t1 due to ! impurity ( ! c>bon disel5ide1 z ! latt] has nev] be5 prep>$ 9 ! pure /ate4 ,ano!r me?od1 :i* is equally attractive because ( its simplicity1 is t ( ,gabriel & ,/elzn]7#eb71 ,,*o ,,*,n _/ ,,nh _/ ,h,o ,c,h ,c,h ,h,n-,,co ,,nh ,,nh ,,nh-,,co ,9 accordance ) ! above reaction o-am9ob5zaldehyde %\ld "w ) equal ease ) sel5oc>bamide1 b ! initial mat]ials 7 n available4 ,! reaction :i* 0 us$ successfully 0 t ( ,bog]t1 ,br5eman & ,h&7#ec71 ,,nh ,,nhcor ,n,,cr _/ _/ _/ ,c,h 7,,rco7,o ,c,h ,c,h ,,csnh ,,cs-,,nh ,,cs-,,nh or ,h,s ,h,s ,n,,cr _/ ,c,h ,,nh ,,nhcor ,c,n _/ _/ ,c,h 7,,rco7,o ,c,h ,,% ,,cn ,,cn ,! hydrog5 sel5ide us$ 9 ! reaction 0 prep>$ f ,fe,se by ! action ( hydro*loric acid1 or by heat+ p>aff9 & sel5ium1 9 ! proportion ( f\r to "o respectively1 at #cce to #cej;,c7#ed74 ,! sel5oqu9azol9e 0 prep>$ f an?ranilic nitrile by ! foll[+ me?ods--! an?ranilic nitrile be+ prep>$ f o-nitranil9e7#eg71 7a7 #bj grams ( acetyl-an?ranilic nitrile 0 dissolv$ 9 absolute alcohol1 & dry hydrog5 sel5ide & dry ammonia pass$ into ! solution = ?ree h\rs4 ,! qu9azol9e cry/alliz$ out gradually on cool+ 0 filt]$ out & recry/alliz$ f dilute alcohol4 ,! yield 0 ab\t t5 p] c5t4 7b7 #aj grams ( acetyl-an?ranilic nitrile 0 heat$ 9 a seal$ tube at #aaj ) alcohol saturat$ at z]o degrees ) dry hydrog5 sel5ide & dry ammonia4 ,aft] five h\rs1 ! tube 0 tak5 out & ! qu9azol9e cry/alliz$ out on cool+4 ,yield 0 ab\t sixte5 p] c5t4 ,z hydrog5 sel5ide 0 some:at un/able & did n dissolve freely 9 alcohol1 fre%ly prep>$ sodium sel5ide 0 us$ 9 ! foll[+ me?od & 0 f\nd to be m satisfactory4 ,x 0 prep>$ f sodium hydroxide 9 absolute alcohol by pass+ dry hydrog5 sel5ide into ! solution = ab\t ?ree h\rs4 ,9 ! beg9n+ & end ( ! reaction1 nitrog5 0 us$ to exclude ! oxyg5 ( ! air4 ,! sel5ide 0 collect$ & dri$ 9 an atmosph]e ( nitrog51 & !n 9 a vacuum1 9 pres5ce ( phosphorus p5toxide4 ,:5 ?us prep>$1 sodium sel5ide 0 colorless1 b on exposure to air x turns r$di% & f9ally d>k color$4 ,! ,c4 ,p4 sel5ide on ! m>ket 0 black & 0 f\nd to be entirely useless4 7c7 #bj grams ( an?ranilic nitrile & fifty grams ( sodium sel5ide 7 mix$ & heat$ 9 a di/ill+ flask 9 an atmosph]e ( nitrog51 & =ty grams ( acetic anhydride dropp$ into ! flask v sl[ly4 ,! temp]ature 0 kept at #aae = half an h\r & !n rais$ to di/ill (f ! acetic acid =m$ 9 ! reaction1 z ! cond5sation h>dly w5t to completion 9 ! pres5ce ( any trace ( acetic acid4 ,! :ole process took an h\r & a half4 ,! flask 0 remov$ f ! oil ba? &1 aft] cool+1 dilute alkali 0 run 91 9 successive portions1 to dissolve out ! qu9azol9e4 ,into ! cle> alkal9e extracts c>bon dioxide 0 bubbl$ = an h\r1 & common salt !n add$4 ,! precipitate 0 recry/alliz$ sev]al times f tw5ty-five p] c5t4 alcohol4 ,! yield 0 f tw5ty to tw5ty-five p] c5t4 7d7 #aj grams ( an?ranilic nitrile1 tw5ty grams ( acetic anhydride1 & tw5ty-five grams ( sodium sel5ide 7 mix$ 9 a seal$ tube & heat$ toge!r = ?ree h\rs & a half at #aaj-aae4 ,! cond5sation product 0 cry/all9e :5 ! tube 0 cool$ to room temp]ature4 ,! cont5ts ( ! tube 7 extract$ ) dilute alkali z be=e1 filt]$1 precipitat$ by c>bon dioxide1 & recry/alliz$ f dilute alcohol4 ,! yield 0 n ov] tw5ty p] c5t4 7e7 ,an attempt 0 made to make o-am9ob5zosel5amide1 & f ! latt]1 by treatm5t ) acetic anhydride1 to =m ! qu9azol9e1 b ! yield ( ! amide 0 too small to c>ry ! reaction fur!r4 ,! sub/ance prep>$ by ! above me?ods cry/allizes f dilute alcohol 9 ne$les or prisms ( d>k br[n color4 ,x melts at #bac4e 7corr474 ,x dissolves readily 9 hot alcohol b on conc5tration sometimes =ms a /icky mass ) a peculi> b n unpleasant odor4 ,x dissolves readily 9 alkalis & is slightly soluble 9 hot b5z5e & *lor(orm1 b insoluble 9 hot wat]4 ,cry/als purifi$ f 7a7 7 analyz$ & gave ! foll[+ results3 ,calculat$ = ,f\nd ,c,h,n,se ,i ,,ii ,c>bon #dh4ch #dh4de #dh4fb ,hydrog5 #c4fa #c4hb #c4eb ,nitrog5 #ab4ee #ab4ea #ab4ff ,sel5ium #ce4df #ce4fj #ce4db ,! cry/als on /&+ 9 ! pres5ce ( air & light decompos$ ) sep>ation ( f9ely divid$ sel5ium & me?yl qu9azolone4 ,analysis ( ,sel5ium ,organic ,comp\nds ,9 ! quantitative det]m9ation ( sel5ium 9 qu9azol9e ! me?od adapt$ by ,beck] & ,mey] 0 f\nd to be q satisfactory7#ef74 ,o!r me?ods are li/$ 9 ! bibliography7#eg74 ,9 ! ultimate analysis ( c>bon & hydrog51 ! ord9>y absolute me?od 0 foll[$ ) ! use ( copp] oxide1 lead *romate1 & lead p]oxide 9 ! tube4 ,9 ! det]m9ation ( nitrog5 ! ord9>y absolute me?od 0 also foll[$ except+ t a consid]able quantity ( specially prep>$ lead *romate p[d] 0 mix$ ) ! sample 9 a numb] six porcela9 boat4 ,?is 0 f\nd to be desirable :5 ! d9itrosel5azole 0 burn$4 ,sel5ium dioxide1 :i* is a solid1 seems to be =m$ 9 ! tube & c>ri$ away by ! curr5t ( c>bon dioxide ) "s difficulty4 ,9 su* a case ! analysis usually took f\r h\rs aft] ! combu/ion _h actually />t$4 ,9 ! c>bon & hydrog5 det]m9ation sel5ium dioxide 0 easily absorb$ 9 ! pres5ce ( oxyg5 gas4 ,prep>ation ( #b-,ph5ylb5zosel5azole ,! fir/ me?od employ$ 0 a modification ( ! me?od describ$ by ,fromm & ,m>t97#eh74 ,me?od 7b7 is an adaptation ( ! me?od = prep>+ b5zo?iazoles4 7a7 ,tw5ty grams ( b5zanilide 0 mix$ 9 a pyrex flask ) #afj grams ( sel5ium du/ & ! flask plac$ 9 a nitrate ba? "u an air cond5s]4 ,aft] heat+ = an h\r at #bbj;,c41 ! temp]ature 0 rais$ to #bej;,c41 & kept at #bej-bhj;,c4 = sixte5 h\rs4 ,! d>k mass 0 extract$ ) hot conc5trat$ ,h,cl1 ! acid extracts filt]$ ?r\gh glass wool us+ a hot wat] funnel4 ,! comb9$ extracts 7 p\r$ into a l>ge volume ( wat] :5 ! sel5azole precipitat$ out imm$iately2 x 0 recry/alliz$ f alcohol4 ,9 "s cases x 0 necess>y to dissolve 9 hot ,h,cl aga9 & to recry/allize4 ,! yield 0 twelve p] c5t4 ,! above me?od has ! disadvantage t wat] is =m$ 9 ! reaction & ?is 9 turn reacts ^u b5zanilid at ! high] temp]ature necess>y 7z sel5ium only melts at #bag;,c471 decompos+ ! b5zanilid into anil9e & b5zoic acid4 ,,nhcoc,h ,n _/ _/ ,c,h ,se ,c,h ,c-,c,h ,h,o _/ ,h ,se ,,nhcoc,h ,,nh _/ _/ ,c,h ,,hoh ,c,h ,,hooc-,c,h ,h ,h ,fur!rmore b5zanilid boils at #afj;,c4 & at su* high temp]atures z #bej;,c4 & ov] "s ( x is apt to be driv5 (f4 7b7 #ajf grams ( b5zaldehyde 7 heat$ ) #ic grams ( r$i/ill$ anil9e at #abj;,c41 = two h\rs or until ! solution 0 cle>4 ,! cle> b5zalanil9e 0 !n p\r$ into #afj grams ( sel5ium du/ 9 a pyrex flask on a s& ba?1 ! flask be+ connect$ ) an air cond5s] z be=e4 ,9 ord] to di/ribute ! flame to bett] advantage ov] ! ba?1 an air space 0 made betwe5 ! ,mek] burn] & ! ba? by introduc+ a wire gauze4 ,hydrog5 sel5ide 0 evolv$ freely4 ,complete reaction took ?ree days4 ,! extraction & recry/allization 7 ! same z 9 ! =m] case4 ,! yield 0 sixty p] c5t4 ,! sel5azole cry/allizes 9 colorless long ne$les1 melt+ at #aag4e;,c4 7corr47 ,fromm & ,m>t97#eh7 gave ! melt+ po9t z #aag;,c4 ,x is insoluble 9 wat]1 & 9 ! foll[+ solv5ts x is lightly soluble 9 ! cold1 m easily hot3 e!r1 me?yl alcohol1 acetone1 acetic acid1 acetic anhydride1 *lor(orm1 & nitrob5z5e4 ,x is difficultly soluble 9 e?yl alcohol1 e?yl acetate1 & c>bon tetra*loride1 9 ! cold1 b easily soluble hot4 ,mononitro ,d]ivative ,! mononitro d]ivative ( ! sel5azole1 #f-nitro-#b-ph5ylb5zo- sel5azole1 0 prep>$ by nitration ) nitric acid at a l[ temp]ature3 ,tw5ty-five grams ( ! sel5azole 7 dissolv$ 9 #aej grams ( conc5trat$ sulphuric acid1 keep+ ! temp]ature bel[ ! room temp]ature until complete solution took place4 ,x 0 !n cool$ on a freez+ mixture & a mixture ( sulphuric & nitric acids 7previ\sly prep>$ & cool$ by mix+ #i4e grams ( nitric & fifte5 grams ( sulphuric acids7 sl[ly dropp$ into x 9 ! c\rse ( half an h\r1 us+ me*anical /irr+ = f\r h\rs4 ,! solution 0 !n p\r$ into two lit]s ( wat] 7ice wat]71 filt]$1 dri$1 & recry/alliz$ f acetic acid1 & alcohol ) ! help ( animal *>coal4 ,! yield 0 #ie p] c5t4 ,?is nitro comp\nd cry/allizes 9 flatt5$ ne$les ( a light yell[ color4 ,x melts at #bjb4d;,c4 7corr474 ,x is v insoluble 9 wat]2 b soluble 9 hot acetic acid1 acetic anhydride1 nitrob5z5e1 nitrotolu5e1 tolu5e1 b5z5e1 alcohol1 & difficultly soluble :5 cold4 ,! cry/als 7 analyz$ & gave ! foll[+ results1 ,calculat$ = ,f\nd ,c,h,n,o,se ,i ,,ii ,nitrog5 #i4bd #i4cf #i4dh ,monoam9o ,d]ivative ,! conv]sion ( mononitro comp\nd to #f-;am9o-#b-ph5ylb5zosel5azole 0 accompli%$ by ! action ( t9 & hydro*loric acid z foll[s3 #cj4c grams ( nitro comp\nd 7 mix$ ) #db grams ( tw5ty me% t9 9 a lit] flask1 imm]s+ ! latt] 9 cold wat]4 #age cc4 ( conc4 ,h,cl 7 sl[ly add$ to ! flask4 ,9 "s cases x 0 necess>y to apply initial heat+ b :5 once ! reaction />t$ x took place rapidly4 ,aft] ! eff]vesc5ce _h abat$1 ! flask 0 heat$ ov] a free flame1 "u a return cond5s]1 = two h\rs4 ,! solution usually turn$ to a pa/y mass1 due to ! =mation ( a t9 d\ble salt4 ,! mixture 0 dissolv$ 9 a l>ge volume ( wat] & heat$ on a wat]-ba?1 ! precipitate filt]$ out1 wa%$1 & pres]v$4 ,! cle> filtrate 0 treat$ ) conc5trat$ alkali1 9 excess1 ! sep>at$ am9e collect$1 wa%$ ) wat]1 dri$ & recry/alliz$ f alcohol1 us+ bone-black4 ,! precipitate set aside 0 treat$ ) /rong alkali1 ! insoluble residue wa%$1 recry/alliz$1 & add$ to ! ma9 product4 ,! yield 0 #ge p] c5t4 ,?is am9e cry/allizes f alcohol 9 f9e yell[i% ne$les1 melt+ at #bja4b-bjb4c;,c 7corr474 ,x is insoluble 9 wat] & e!r1 difficultly soluble 9 ! hot2 & fairly soluble 9 anil9e4 ,a pure sample 0 analyz$ & gave ! foll[+ results3 ,calculat$ = ,f\nd ,c,h,n,se ,i ,,ii ,nitrog5 #aj4be #aj4cd #aj4db ,c>bon #eg4ah #eg4ag #eg4jj ,hydrog5 #c4fi #c4gi #c4he ,decomposition ( ,monoam9o ,d]ivative ,five grams ( ! monoam9o comp\nd 7 mix$ ) p[d]$ ,,koh1 heat$ toge!r until ! mixture j melt$1 & ma9ta9$ 9 t /ate = a few m9utes4 ,:5 ! latt] _h cool$ d[n to room temp]ature1 cold wat] 0 p\r$ ov] ! mixture4 ,! filt]$ solution 0 acidifi$ until no fur!r precipitate 0 =m$4 ,! precipitate 0 collect$ & recry/alliz$ f wat]1 m4p4 #aba;,c4 ,"o gram ( ?is solid 0 plac$ 9 a te/ tube1 provid$ ) a cork & a deliv]y tube1 & heat$ ) soda lime2 a liquid ) ! smell ( b5z5e 0 collect$ 9 ano!r te/ tube cool$ ) wat]4 ,:5 ?is liquid 0 treat$ ) a few drops ( nitric acid mixture ! smell ( nitrob5z5e 0 giv5 (f4 ,a gram ( ! cry/als 0 heat$ ) conc5trat$ sulphuric acid & alcohol :5 ! odor ( e?yl b5zoate 0 not$4 ,monacetyl ,d]ivative ,five grams ( ! monoam9o sel5azole 7 heat$ on a wat]-ba? ) #aj cc4 ( acetic anhydride until ! solution 0 cle>1 :i* took ab\t two h\rs4 #ajj cc4 ( wat] 7 p\r$ into ! mixture1 :i* 0 !n neutraliz$ ) dilute ammonium hydroxide4 ,! precipitate 0 filt]$1 decoloriz$ by animal *>coal1 & recry/alliz$ f dilute alcohol4 ,! acetyl comp\nd1 #f-;acetam9o-#b-ph5ylb5zosel5azole1 =ms colorless cry/als1 melt+ at #ahh4a-4g;,c4 7corr474 ,x is insoluble 9 e!r1 b5z5e1 c>bon disulphide2 slightly soluble 9 tolu5e2 soluble 9 alcohol1 e?yl acetate1 amyl acetate1 acetone1 & acetic acid4 ,a pure sample 0 analyz$ & gave ! foll[+ result1 ,calculat$ = ,c,h,n,se,o ,f\nd ,nitrog5 #h4hh #h4ib #h4fh ,monob5zylid5e ,d]ivative ,five grams ( ! monoam9o comp\nd 7 dissolv$ 9 #bjj cc4 absolute alcohol ) ! addition ( #c cc4 ( b5zaldehyde & ! cle> solution 0 boil$ on a wat]-ba?1 ) a return cond5s]1 = two h\rs4 ,aft] ! solution 0 boneblack$1 ! yell[ precipitate 0 recry/alliz$ f c>bon disulphide4 ,! yield 0 #ij p] c5t4 ,x cry/allizes 9 yell[ plates1 melt+ at #aef4g-aeg4f;,c41 soluble 9 b5z5e1 e!r1 e?yl alcohol1 c>bontetra*loride1 acetone1 b difficultly soluble 9 ligro94 ,an analysis ( ! cry/als %[$ ! foll[+ result1 ,calculat$ = ,c,h,n,se ,f\nd ,nitrog5 #g4ge #g4ib #g4fh ,an ,azo ,dye ,five & f\r t5? grams ( ! monoam9o comp\nd 7 dissolv$ 9 hot conc4 ,h,cl1 cool$ 9 ice1 & diazotiz$ ) sodium nitrite solution1 until />* iodide pap] %[$ excess nitr\s acid4 ,! diazotization 0 p]=m$ 9 ice1 ) me*anical /irr+1 & requir$ ab\t an h\r4 ,! diazo solution 0 p\r$ into a solution ( #c grams ,b-naph?ol 9 #h grams ( ,na,o,h & #fj cc4 ( wat]1 :ile gradually /irr+4 ,a v deep r$ solution =m$4 ,?is 0 acidifi$ ) excess ,h,cl1 salt$ out by ,na,cl1 & cry/alliz$ f anil9e-alcohol mixture4 ,9 ! pure /ate1 x is a deep r$ p[d]1 ) a metallic lu/re :5 rubb$1 melt+ at #bhd4b;,c4 ,an analysis %[$ ! foll[+ result1 ,calculat$ = ,c,h,n,o,se ,f\nd ,nitrog5 #i4ha #i4ge ,d9itro ,d]ivative ,! nitration = ! production ( d9itro d]ivative 0 at fir/ c>ri$ out "u ! same conditions z 9 ! prep>ation ( mononitro comp\nd & aft] ! latt] 0 =m$ m nitric acid mixture 0 add$ ) ! addition ( heat3 conc4 sulphuric acid1 keep+ x bel[ room temp]ature4 ,x 0 !n cool$ 9 a freez+ mixture & half ! volume ( a nitric acid mixture 7prep>$ & cool$ by mix+ #ai grams ( nitric & #cj grams ( sulphuric acids7 0 introduc$ v sl[ly to ! sel5azole solution ?r\gh a dropp+ funnel1 ma9ta9+ at ?is temp]ature = two h\rs 7us+ me*anical /irr+74 ,! rema9+ half ( ! nitric acid mixture 0 !n sl[ly introduc$ & ! flask 0 heat$ on a wat]-ba? = two h\rs4 ,! solution 0 p\r$ into two lit]s ( wat]1 ! precipitate filt]$ (f1 dri$ & recry/alliz$ sev]al times f acetic acid4 ,! yield 0 #hj p] c5t4 ,?is d9itro comp\nd cry/allizes 9 f9e yell[ ne$les1 m4 p41 #bdf4h;,c4 7corr471 v insoluble 9 wat]1 b soluble 9 hot acetic acid1 acetic anhydride1 nitrob5z5e1 nitrotolu5e1 e?yl alcohol1 & difficultly soluble cold4 ,x 0 analyz$ & ! foll[+ results 7 f\nd1 ,calculat$ = ,f\nd ,c,h,n,o,se ,i ,,ii ,nitrog5 #ab4jg #ab4cj #ab4ab ,diam9o ,d]ivative ,! conv]sion ( ! d9itro to diam9o d]ivative 0 accompli%$ 9 ! same mann] z ! r$uction ( ! mononitro d]ivative except+ t twice z mu* t9 & ,h,cl 7 us$4 ,?is diam9o comp\nd cry/allizes 9 yell[i% gli/5+ ne$les f alcohol & pyrid9e2 m4 p41 #bfi-bgj4e;,c42 0 analyz$ & gave ! foll[+ results1 ,calculat$ = ,f\nd ,c,h,n,se ,i ,,ii ,nitrog5 #ad4f #ad4d #ad4g ,diacetyl & ,dib5zylid5e ,d]ivatives ,! diacetyl & dib5zylid5e comp\nds 7 also prep>$ f ^! diam9o d]ivatives4 ,! =m] cry/allizes 9 cubes f dilute alcohol2 m4 p41 #cjg;,c 7,corr47 & ! latt] 9 beautiful yell[ plates f c>bon disulphide1 m4 p41 #aie-aif;,c4 7,corr474 ,an analysis ( ^! two comp\nds %[$ ! foll[+ results1 ,calc4 = ,calc4 = ,f\nd ,c,h,n,o,se ,c,h,n,se ,i ,,ii ,nitrog5 #i4je #aa4ba #i4ba #aa4dc ,dye+ ) ,azo ,dyes ,bo? ! monoam9o & ! diam9o d]ivatives =m int5sely color$ dyes :5 diazotiz$ & c\pl$ ) ph5ols & aromatic am9es4 ,! dyes =m$ are fa/ to light4 ,9 ! foll[+ table silk is giv5 to repres5t ! fabrics us$4 ,wool & cotton 7 dy$ simil> %ades1 ?\gh ) slight v>iation4 ,ea* silk sample 0 dy$ 9 acid or alkal9e ba?s z indicat$ & ea* ba? conta9$ #j4ja gram 9 tw5ty cc4 solution3 ,diazo4 ,on ,diazo4 ,on ,c\pl] monoam9e silk diam9e silk ,ph5ol deep r$ v4 light 7alk7 yell[ 7alk7 yell[ deep r$ ,dime?ylanil9e orange light orange-r$ yell[ 7acid7 yell[ 7acid7 ,p-nitranil9e light br[ni% grayi% br[n 7acid7 br[n 7acid7 ,p-toluid9e light br[ni% br[ni% br[n 7acid7 7acid7 ,pyrogallic d>k grayi% d>k grayi% acid br[n br[n 7acid7 7alk7 ,salicylic r$di% light r$ br[n acid 7alk7 br[n 7alk7 ,b-naph?ol deep r$ p9k deep r$ r$ 7alk7 7alk7 ,sulphanilic light br[ni% br[n br[n acid br[n 7alk7 7alk7 ,a-naph?ylam9e light br[ni% yell[ yell[ br[n 7acid7 7acid7 ,resorc9ol purple r$ d>k deep r$ 7alk7 purple 7alk7 ,,bibliography #a4 ,b]zelius1 ,annales de ,physique et ,*imie 7#b7 #i1 #bci1 #cef 7#ahah74 #b4 ,gmel9-,kraut1 8,h&bu* d] ,anorg4 ,*emie0 ,i 7#a7 #gje-hjd2 ,roscoe & ,s*orlemm]1 8,treatise on ,*emi/ry0 ,i1 #dfg-hb 7#aibj72 ,br[n+1 8,introduction to ! ,r>] ,elem5ts10 #add-eb 7#aiag74 #c4 ,victor ,l5h]1 ,j4 ,ind4 ,eng4 ,*em41 #ab1 #eig 7#aibj74 #d4 ,le ,sel5eum et ses applications actuelles1 ,*imie et ,indu/rie 7#aiai7 #bde4 #e4 ,c4 ,r4 ,boggs1 ,u4 ,s4 ,a41 #a1bdi1bgb2 ,j4 ,ind4 ,eng4 ,*em4 #aj1 #aag-h 7#aiah74 #f4 ,duhamel ,robi]e1 ,compt4 r5d4 soc4 biol4 #gb1 #fgj 7#aiac72 ,am4 ,*em4 ,abs4 #g1 #bfbd 7#aiac74 #g4 ,b4 ,g4 ,duhamel1 ,compt4 r5d4 soc4 biol41 #gb1 #hfe 7#aiac72 ,am4 ,*em4 ,abs4 #g1 #biga 7#aiac74 #h4 ,duhamel ,juill>d1 ,compt4 r5d4 soc4 biol41 #gb1 #gad 7#aiac72 ,am4 ,*em4 ,abs41 #g1 #bfbd 7#aiac74 #i4 ,b4 ,g4 ,duhamel1 ,compt4 r5d4 soc4 biol41 #hb1 #gbd-f 7#aiai72 ,am4 ,*em4 ,abs4 #ad1 #bchc 7#aibj74 #aj4 ,wass]mann1 ,d4 ,r4 ,p41 #bfa1eef2 #bhf1iej2 #bhg1jbj4 #aa4 ,a4 v4 ,wass]mann1 ,keys]1 ,m4 ,wass]mann1 ,duet4 ,m$4 ,wo*41 #cg1 #bchi 7#aiaa72 ,am4 ,*em4 ,abs41 #f1 #fej 7#aiab74 #ab4 ,a4 v4 ,wass]mann ,hansmann1 ,b]l4 kl94 ,wo*41 #di1 #d1 7#aiaa72 ,am4 ,*em4 ,abs41 #f1 #hij 7#aiab74 #ac4 ,an?raqu9one dyes1 ,d4 ,r4 ,p41 #bef1ffg4 #ad4 ,p4 ,ehrli* ,h4 ,bau]1 ,b]41 #dh1 #ejb 7#aiae74 #ae4 ,b]zelius1 ,lehrbu* 7#e ,aufl47 #b1 #bac2 ,roscoe & ,s*orlemm]1 8,treatise on ,*emi/ry10 ,i1 #dgc 7#aibj74 #af4 ,bru]e1 ,j4 ,anat4 ,physiol41 ,oct41 7#ahia74 #ag4 ,t4 ,w4 ,cl>ke ,w4 ,h4 ,hurtley1 ,j4 ,physiol41 #cf1 #fb 7#aijg74 #ah4 ,hugo ,bau]1 ,b]41 #dg1 #ahgc 7#aiad74 #ai4 ,ehrli* ,guttmann1 ,b]l4 kl94 ,wo*4 7#ahia7 #bh2 ,u4 ,s4 ,disp41 #bj? ,edition4 #bj4 ,p4 ,k>r]1 #di1 #eig 7#aiaf72 ,b]41 #ea1 #aij 7#aiah74 #ba4 ,hugo ,bau]1 ,b]41 #dg1 #ahgc 7#aiad72 ,d4 ,r4 ,p41 #bfa1ifi2 ,fri$l41 #aa1 #aabd 7#aiac74 #bb4 ,sel5az9es1 ,d4 ,r4 ,p41 #bhj1gac2 #bfa1gic4 #bc4 ,u4 ,s4 ,disp41 #bj? ,edition4 #bd4 ,d4 ,r4 ,p41 #cje1bfb2 #cje1bfc2 ,am4 ,*em4 ,abs41 #ac1cbe 7#aiah74 #be4 ,bull4 soc4 *im41 #da1 #eii2 ,compt4 r5d41 #ii1 #aaed-g 7#ahhe72 ,brit4 ,*em4 ,abs41 #ej1 #cgf 7#ahhe72 ,a4 ,*41 7#f7 #i1 #bid1 #cjc1 #cbc4 #bf4 ,w4 ,b>+]1 ,b]41 #bc1 #ajjc 7#ahhi74 #bg4 ,p4 ,spica1 ,gazz4 *im4 ital41 #g1 #ij-i 7#ahgg72 ,brit4 ,*em4 ,abs41 7#ahgg7 ,,ii1 #ahi2 ,compt4 r5d41 #ii1 #aaed 7#ahhd72 #ajj1 #abif 7#ahhe72 ,fr]i*s1 ,ar*4 ,ph>m41 #bda1 #ahj1 #aif2 ,beil41 7#aiba7 ,,iii1 #bie1 #bfa4 #bh4 ,c4 ,paal1 ,b]41 #ah1 #bbee 7#ahhe72 ,gazz4 *im4 ital41 7,i4 ,zoppell>i7 #bd1 ,,ii1 #cii1 7#ahid74 #bi4 ,ida ,foa1 ,gazz4 ,*im4 ital41 #ci1 ,,ii1 #ebg1 7#aiji72 ,c-,b41 7#aiaj7 ,i1 #hcg4 #cj4 ,d4 ,r4 ,p41 #bfd1aci4 #ca4 ,o4 ,h9sb]g1 ,b]41 #bb1 #hfb1 #bhie 7#ahhi72 ,d4 ,r4 ,p41 #bfa1dab4 #cb4 ,j4 prakt4 ,*em41 7#aijd7 ,,ii1 #fi1 #eji4 #cc4 ,e4 ,abd]hald51 ,h&4 ,biol4 ,*em41 ,,iii1 #b1 #ied4 #cd4 ,hanzlik ,t>r1 ,am4 ,univ4 ,ezpt4 ,/a41 ,j4 ,ph>macol1 #ad1 #bba-h 7#aiai74 #ce4 ,ho*/1 ,d4 ,r4 ,p41 #bii1eaj4 #cf4 ,d4 ,r4 ,p41 #bfd1idj2 #bfd1ifa4 #cg4 ,a4 ,mi*aelis ,m4 ,/e91 ,ann41 #cbj1 #cb 7#aijb74 #ch4 ,bog]t ,h&1 ,j4 ,am4 ,*em4 ,soc41 #be1 #cgg 7#aijb74 #ci4 ,b4 ,ba?ke1 ,ann41 #aeb1 #baj 7#ahfi72 ,ann41 #ahe1 #cca2 ,ri*t]1 ,organis*e ,*emie1 ,i1 #aff4 #dj4 ,less] ,s*oell]1 ,b]41 #dg1 #bbic 7#aiad74 #da4 ,less] ,weiss1 ,b]41 #de1 #ahce 7#aiab72 #df1 #bfec1 7#aiac74 #db4 ,wohl] ,dean1 ,ann41 #ig1 #e 7#ahef72 ,b4 ,ra?ke1 ,ann41 #aeb1 #baa 7#ahfi74 #dc4 ,cah\rs1 ,ann41 #fa1 #ib1 7#ahdg72 #ib1 #cef4 #dd4 ,h4 ,kl+]1 ,b]41 #cb1 #baie1 7#ahii72 ,ann41 #aai1 #ia2 #aba1 #ajh4 #de4 ,c4 ,a4 ,joy1 ,ann41 #hf1 #ce1 7#ahec72 ,b4 ,ra?ke1 ,ann41 #aeb1 #bab1 #bai 7#ahfi74 #df4 ,:eel]1 ,z4 ,*em41 7#ahfg7 #dcf4 #dg4 ,krafft ,lyons1 ,b]41 #bg1 #agfb 7#ahid72 ,a4 ,*41 7#f71 #bj1 #bbh4 #dh4 ,k4 ,a4 ,h(fmann1 ,b]41 #bg1 #bhji 7#ahid74 #di4 ,m4 ,bus*1 ,b]41 #be1 #bhec1 7#ahib74 #ej4 ,lellmann ,/ickel1 ,b]41 #ai1 #afje 7#ahhf74 #ea4 ,b4 ,ra?ke1 ,ann41 #aeb1 #bja 7#ahfi74 #eb4 ,gabriel ,/elzn]1 ,b]41 #bi1 #acac 7#ahif74 #ec4 ,bog]t1 ,br5eman1 ,h&1 ,j4 ,am4 ,*em4 ,soc41 #be1 #cgc 7#aijc74 #ed4 ,am4 ,*em4 ,abs41 #c1 #hgj 7#aijc72 ,bull4 ,belg4 ,soc4 ,*em41 #bc1 #i-aa4 #ee4 ,bog]t ,h&1 ,j4 ,am4 ,*em4 ,soc41 #bd1 #ajce1 7#aijb74 #ef4 ,beck] ,mey]1 ,b]4 #cg1 #beea 7#aiad74 #eg4 ,h4 ,bau]1 ,b]4 #dh1 #ejg 7#aiae72 ,lyons ,%9n1 ,j4 ,am4 ,*em4 ,soc4 #aijb3 #ajib2 ,fritz von ,konek ,o4 ,s*leif]1 ,b]4 #ea1 #hej 7#aiah72 ,a4 ,mi*aelis1 ,b]4 #cj1 #bhbg 7#ahig72 ,b]4 #dh1 #hgc 7#aiae72 ,h4 ,fr]i*s1 ,ar*4 ,ph>m4 #aijb3 #bdj1 #fef4 #eh4 ,fromm ,m>t91 ,ann41 #dja1 #agh 7#aiac74 ,,vita ,y-,gwan ,*5 0 born 9 ,nank+1 ,*9a1 ,m>* #h1 #ahic4 ,aft] graduation f college 9 #aiae1 he fur!r /udi$ ,*9ese classics1 #aiae-af4 ,he ent]$ ,case ,s*ool ( ,appli$ ,sci5ce1 ,clevel&1 ,ohio1 z a special /ud5t 9 ! ,dep>tm5t ( ,*emi/ry1 #aiaf-ag4 ,he regi/]$ at ,columbia ,univ]sity to pursue graduate "w 9 *emi/ry "u ! ,faculty ( ,pure ,sci5ce2 & 0 aw>d$ ! degree ( ,ma/] ( ,arts 9 #aiah4 ,f ,septemb] #aiai to ,june #aibb1 he has be5 pursu+ rese>* 9 organic *emi/ry 9 ! rese>* laboratories ( ,havemey] ,hall1 ,columbia ,univ]sity4 ,,footnotes3 ,a ,n a new comp\nd b prep>$ by a diff]5t me?od4 ,b ,note--dime?yl sel5oph5e1 h[ev]1 is colorless4 ,transcrib]'s notes3 ,! diagram ( #c-7p-ph5yl>sonic7-am9osel5az9e1 labell$ 7,,ii71 has be5 adju/$ to make its /ructure cle>]4 ,! l 9 #b;,h,cl 9 ! fir/ equation "u ,prep>ation ( #b-me?yl-#d-sel5oqu9azolone 0 miss+ 9 ! orig9al4 ,! foll[+ is a li/ ( *anges made to ! orig9al4 ,! fir/ l9e is ! orig9al l9e1 ! second ! correct$ "o4 selnoqu9azolone prep>$ 9 ! c\rse ( ?is rese>* sel5oqu9azolone prep>$ 9 ! c\rse ( ?is rese>* on f\r diff]5t /ra9s ( m\se c>c5oma & "o /ra9 on f\r diff]5t /ra9s ( m\se c>c9oma & "o /ra9 9 consequ5ce ( its smell ,i s completely loss my s5se ( smell 9 consequ5ce ( its smell ,i s completely lo/ my s5se ( smell ( ! ph5az9e1 oxas9e1 ?iaz9e1 acrid9e s]ies %[ ( ! ph5az9e1 oxaz9e1 ?iaz9e1 acrid9e s]ies %[ & ,se aga9 mo/ p[]ful ( ! :ole s]ies4 & 3,se aga9 mo/ p[]ful ( ! :ole s]ies4 simplicity1 is t ( ,babriel & ,/elzn]7#eb71 simplicity1 is t ( ,gabriel & ,/elzn]7#eb71 on cool+ 0 filt]$ out & recry/aliz$ f dilute alcohol4 on cool+ 0 filt]$ out & recry/alliz$ f dilute alcohol4 ,x 0 prep>$ f ,sodium hydroxide 9 absolute alcohol ,x 0 prep>$ f sodium hydroxide 9 absolute alcohol a seal$ tube at #aaj ) alcohol saturat$ at z]o degree ) a seal$ tube at #aaj ) alcohol saturat$ at z]o degrees ) took an h\r & half4 ,! flask 0 remov$ f ! oil took an h\r & a half4 ,! flask 0 remov$ f ! oil ,! precipitrate 0 recry/alliz$ sev]al times ,! precipitate 0 recry/alliz$ sev]al times 7e7 ,an attempt 0 made to make o-am9ob5zsel5amide1 7e7 ,an attempt 0 made to make o-am9ob5zosel5amide1 ,x dissolves readily 9 alkalies & is slightly soluble ,x dissolves readily 9 alkalis & is slightly soluble ,?is 0 f\nd to be desirable :5 ! d9itroselezazole 0 burn$4 ,?is 0 f\nd to be desirable :5 ! d9itrosel5azole 0 burn$4 into a l>ge volume ( wat] :5 ! sel5ozole precipitat$ out into a l>ge volume ( wat] :5 ! sel5azole precipitat$ out x 0 necess>y to dissolve 9 hot ,h,cl aga9 & to recry/alize4 x 0 necess>y to dissolve 9 hot ,h,cl aga9 & to recry/allize4 7b7 #ajf grams ( b5aldehyde 7 heat$ ) #ic grams ( 7b7 #ajf grams ( b5zaldehyde 7 heat$ ) #ic grams ( ,x is difficulty soluble 9 e?yl alcohol1 e?yl acetate1 & ,x is difficultly soluble 9 e?yl alcohol1 e?yl acetate1 & tolu5e1 b5z5e1 alcohol1 & difficulty soluble :5 cold4 tolu5e1 b5z5e1 alcohol1 & difficultly soluble :5 cold4 f alcohol 9 f9e yell[i% ne$les1 melt+ at #bja4bbjb4c;,c f alcohol 9 f9e yell[i% ne$les1 melt+ at #bja4b-bjb4c;,c c>bontetra*loride1 acetone1 b difficulty soluble 9 ligro94 c>bontetra*loride1 acetone1 b difficultly soluble 9 ligro94 #ai grams ( nitric & #cj grams ( sulphuric acids 0 introduc$ #ai grams ( nitric & #cj grams ( sulphuric acids7 0 introduc$ 9 ! same mann] z ! r$uction ( mononitro d]ivative 9 ! same mann] z ! r$uction ( ! mononitro d]ivative ,?is diam9o comp\nd cry/alizes 9 yell[i% gli/5+ ne$les ,?is diam9o comp\nd cry/allizes 9 yell[i% gli/5+ ne$les comp\nds 7 also prep>$ f ?is diam9o d]ivatives4 comp\nds 7 also prep>$ f ^! diam9o d]ivatives4 ,! =m] cry/alizes 9 cubes f dilute alcohol2 ,! =m] cry/allizes 9 cubes f dilute alcohol2