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Dhammaan Waxaad u Baahan Tahay Inaad Ka Ogaato Pyridines

Dhammaan Waxaad u Baahan Tahay Inaad Ka Ogaato Pyridines

Dhamaan waxaad u baahan tahay inaad ogaato Pyridines

Pyridine waa aasaaska heterocyclic Qayb ka mid ah nooca yar. Pyridine waxaa laga soocaa bakteerka iyada oo loo beddelayo kooxda CH-da N-atom. Qaab dhismeedka Pyridine wuxuu u dhigmaa qaab dhismeedka baasiin, maxaa yeelay waxay ku xirantahay bedelida kooxda CH. N. Farqiga ugu weyn waxaa ka mid ah:

  1. Ka bixitaanka geometry-ga caadiga ah ee joogtada ah ee joogtada ah sababtoo ah joogitaanka hetero atom, si gaar ah, cufnaanta nitrogen-carbon gaaban,
  2. Beddelida atomi atomi ah ee duubista giraanta oo leh lamaanaha unugyada korontada ku shaqeeya, sida duubista giraanta, oo ku dhex yaal sp2 hybrid orbital, oo aan ku jirin sextet p-elektar. Lafatankan nitrogen wuxuu mid ka mid ah mas'uul ka yahay guryaha asaasiga ah ee pyridines,
  3. Dipole joogta ah oo si joogto ah loo raadin karo koranto sare oo ka mid ah atomiga nitrogen marka la barbar dhigo atomi bir ah.

Giraanta Pyridine waxay ku dhacdaa dhowr xeryood oo muhiim ah, oo ay ku jiraan fitamiinada niacin, pyridoxine, iyo sidoo kale asiin.

Farmashiyaha Scottish-ka, Thomas Anderson wuxuu soo saaray pyridine-ka 1849 mid ka mid ah xeryaha loo yaqaan saliida lafaha. Labo sanno ka dib, Anderson wuxuu ka soo baxay pyridine saafi ah oo leh jajabyo kala duwan oo saliid ah. Waa dareer aad u olal leh oo aan gubanayn, biyo-qoyan, dareeraha leh alkaliin leh oo aan fiicnayn, urin kalluun.

Pyridine waxaa marwalba loo adeegsadaa sidii daawo iyo daawo xoolo dhaqato, sidoo kale waa mid muhiim ah oo wax lagu kariyo. Pyridine waxaa lagu dari karaa ethanol haddii aad rabto inaad ka dhigto mid aan habooneyn isticmaalka aadanaha. Waxa kale oo lagu dabaqi karaa soo saarida mepyramine antihistaminic iyo tripelennamine, in vitro dhajinta DNA, ee wax soo saarka sulfapyridine (daawo loogu talagalay daweynta caabuqyada fayras iyo caabuqyada bakteeriyada), iyo sidoo kale bakteeriyada, herbicides, iyo celinta biyaha.

Qaybaha kiimikada badankood, xitaa haddii aan laga soo saarin pyridine, waxaa ku jira qaab dhismeedka giraanta. Xeryaha noocan oo kale ah waxaa ka mid ah fitamiin B sida pyridoxine iyo niacin, nicotin, waxyaallaha dhirta nitrogen-ku jira, iyo daawada ka hortagga qaaxada loo yaqaan 'isoniazid'. Pyridine waxaa taariikh ahaan loo soo saaray sidii koriinka dhuxusha iyo dhuxusha. Si kastaba ha ahaatee, baahida loo qabo kor u kaca ee pyridine ayaa horseeday horumarinta habab dhaqaale ee wax soo saarka ammonia iyo acetaldehyde, iyo in ka badan 20,000 tonnes ayaa la soo saaraa sannad kasta.

Nomenclature of pyridine

Magaca nidaamsan ee pyridine, sida ay sheegayso magaca Hantzsch-Widman ee soo jeediyay IUPAC, waa azine. Laakiin magacyada nidaamsan ee xeryahooda aasaasiga ah ayaa loo isticmaalaa marar dhif ah; Taa baddalkeeda, magacaabida heterocycles waxay raacdaa magacyo caadi ah. IUPAC ma dhiirigalinayso isticmaalka azine markaad tixraacayso pyridine.

Tirinta xakameynta giraanta ee azine waxay ka bilaabataa nitrogen. Qoondaynta boosaska xarafka Giriigga (α-γ) iyo qaabka beddelka magacaabidda ee caadiga ah ee nidaamka Homoaromatic (para ortho, gool,) waxaa loo isticmaalaa marmarka qaarkood. Halkan α, β iyo γ tixraac labada, saddex, iyo afar jagadood, siday u kala horreeyaan.

Magaca habaysan ee loogu talagalay walxaha ku jira pyridine waa piridinyl, halkaas oo lambar ka hor inta aan aheyn bedelka atomiga ee la beddelay ka hor. Laakiin magaca taariikhiga ah pyridyl waxaa lagu talinayaa IUPAC oo loo adeegsaday meel magac leh. Wabida waxaa lagu sameeyey iyada oo loo sii marinayo qalabka elektarooniga ah ee atomiga nitrogen waxaa loo yaqaanaa sida pyridinium.

4-bromopyridine

2,2'-bipyridine

Dipicolinic acid (pyridine-2,6-dicarboxylic acid)

Nooca aasaasiga ah ee sharraxa pyridinium

Wax soo saarka pyridine

Pyridine waxaa loo heley sidii dhirta dhuxusha ama laga soo saaro dhuxusha. Habkani wuxuu ahaa mid aan fiicneyn oo shaqaaleynaya: dhirta dhuxusha waxay haysaa 0.1 boqolkiiba pyridine, sidaas darteedna loo baahan yahay in la nadiifiyo dhowr marxaladood, taas oo hoos u dhigtay wax soo saarka. Maanta, pyridine inta ugu badan waa la soo saaray iyadoo loo adeegsanayo ficilo magac badan, kuwa ugu caansan ayaa laga wada hadlay halkan hoose.

Pyridine Synthesis iyada oo loo marayo Bohlmann-Rahtz

Pyridine Synthesis iyada oo loo marayo Bohlmann-Rahtz ayaa u oggolaanaya soo saarida pyridines ee la badalay laba tallaabo oo waaweyn. Cunto-qaadista dhalooyinka oo isticmaalaya ethynylketones waxay keenaysaa dhexdhexaadiyaha aminodiinka kaas oo, ka dib markii isomerization-kuleylka loo yaqaan "heat-caused, isomerization", waxaa laga helaa cyclodhydration si loo soo saaro pyridines 2,3,6-trisubstituted.

Pyridine Synthesis iyadoo loo marayo habka Bohlmann-Rahtz

Farsamadani waxay la xiriirtaa caansaanka Hantzsch Dihydropyridine ee halkaa ku yaalin situNooca la dhalaaliyay iyo noocyada cayayaanka ayaa soo saaraya dihydropyridines. Inkasta oo Bohlmann-Rahtz Synthesis uu yahay mid aad u sarreeya, daahirinta heerkulka dhexe ee heerarka sarre ee loo baahan yahay duufaan la'aanta ayaa ah caqabado ku kooban xaddiga adeegsiga. Dhibaatooyinka intooda badani way ka badan yihiin, taasoo Bohlmann-Rahtz Synthesis ka dhigtay mid aad u muhiim ah pyridines Jiilka.

Inkastoo ma jirto baaris farsamo oo la sameeyey, dhexdhexaadiyeyaasha waxaa lagu tilmaami karaa H-NMR. Tani waxay muujinaysaa in badeecada ugu weyn ee Michael Addition iyo kala iibsiga protons ee soo socda ay noqon karaan 2Z-4E-heptadien-6-mid waa la soo saaraa oo la nadiifiyaa iyada oo loo marayo shaxanka shaxanka.

Heer sarreysa oo heerkul ah ayaa loo baahan yahay si loo fududeeyo Z/E isomerizations taas oo ah shardi u ah heteroannelation.

Noocyo dhowr ah oo u oggolaanaya in la soo dhejiyo tetra iyo pyridines trisubstituted oo hal mar ah ayaa la sameeyey horaantii. Intii la isticmaali lahaa adeegsiga butynone sida substrate ah, Bagley ayaa tijaabiyay dareerayaal kala duwan ee loogu talagalay is-beddel la'aanta 4- (trimethylsilyl) laakiin-3-yn-2-mid. Waxaa la muujiyey in kaliya DMSO iyo EtOH ay yihiin kuwo ku habboon. EtOH ayaa si cad loogu riyaaqay inay noqoto qulqulka iyo xajmiga difaaca DMSO sida qalabka wax lagu daboolo. Labada xal, protodilylation wuxuu u dhacay si isdaba joog ah. Bagley ayaa sidoo kale muujisay in kicinta hawada loo oggol yahay in wareegga duufaanku uu sii wado heerkulka hoose.

Xinjirta xajiinta ayaa sidoo kale xoojisa iskudarka xambaarsan. Noocyo balaadhan oo laysku qurxiyo ayaa laga soo qaaday kiniinada ethynyl ee (5: 1) isku dar ah acetic acid iyo toluene si loo helo qiimaha pyridines ee shaqeynaya hal tallaabo ee dhalidda fiican.

Ka dib guusha baayac-mushtarka Brønstedt, farmashiga ayaa baadhay awooda Lewis acid-ka. Xaaladaha ugu wanaagsan ee loo isticmaalo labaatan mile% ytterbium triflate ama shan iyo toban mitir% zinc bromide ee qashinka lagu soo celiyo. Inkasta oo cilmi-baaris la'aanta aan la sameynin, waxaan u qaadan karnaa in isku-duwidda ay xambaarsan tahay xajinta ay xoojiso isbeddelka duufaanta, Michael Addition, iyo tallaabooyinka isomerization.

Dhimashadu waa isku-filnaansho xaddidan oo leh aalado-dhexdhexaad ah. Tusaale ahaan, jajabyada cad-cadaynta ee enamines waxaa lagu qabtaa cyano iyo qiyaastii-butilester sida kooxaha iskaashiga elektarooniga ah. Hab kale oo khafiif ah waa codsiga Amberlyst-15 iyio isweydaarsiga ra'yiga oo u dulqaadanaya qiyaastii-butylesters.

Maadaama mashiinnada aan si fudud loo helin, iyo in lagu xoojiyo xarunta geeddi-socodka, fal-celinta 3-ga waxaa loo qaaday iyada oo la adeegsanayo ammonium acetate oo ah halka laga soo xigtay kooxda amniga. Nidaamkan wax-ku-oolka ah, enamine ayaa la sameeyay in situ taas oo ka soo horjeeda joogitaanka alkynone.

Marka hore tijaabada, ZnBr2 iyo AcOH ayaa loo isticmaalay sidii kalluumeyaal dheeri ah leh toluene sida dareeraha. Si kastaba ha ahaatee, tan iyo markii la soo bandhigay in dusha xasaasiga ah ee astaamuhu ay mar walba cabiraan jawi sahlan oo leh EtOH oo ah dareer.

Chichibabin Synthesis

Baadhitaanka Pichidine Chichibabin ayaa markii ugu horraysay lagu soo warramey 1924 waxaana wali ah codsi weyn oo ku jira warshadaha kiimikada. Waa fal-celin fara-gelineed, taas oo ku lug leh fal-celinta kicinta ee aldehydes, ketones, α, β-ku-maaddooyinka carbonyl carbonyl. Waxaa intaa dheer, qaabka guud ee dareen-celinta waxaa ka mid noqon kara wax kasta oo isku dhafan oo ka mid ah alaabooyinka kor ku xusan ee ammonia saafi ah ama derisyo.

Abaabulida Pyridine

Kicinta ee rasaaseed iyo acetaldehyde

Formaldehyde iyo acetaldehyde badanaa waa ilaha pyridine aan la beddelin. Ugu yaraan, waxay yihiin kuwo la awoodi karo oo la heli karo.

  1. Tallaabada ugu horreysa waxay ku lug leedahay samaynta acrolein laga bilaabo formaldehyde iyo acetaldehyde iyada oo loo marayo Knoevenagel kondensation.
  2. Suufka dhammaadka ayaa markaa ka soo baxa acrolein leh acetaldehyde iyo ammonia, kaas oo sameeya dihydropyridine.
  3. Nidaamka kama dambaysta ah waa fal-celin oxidation ah oo leh mashiinka adag-adag si loo siiyo pyridine.
  4. Xasaasiyadda kor ku xusan waxay ku dhacdaa marxalad gaas ah iyadoo leh heerkulka 400-450 ° C. Maaddada la sameeyay waxay ka kooban tahay pyridine, picolin ama pyridines fudud oo fudud, iyo lutidine. Si kastaba ha ahaatee, halabuurka wuxuu ku xiran yahay xayiraadaha isticmaalka iyo illaa xad, waxay ku xirantahay baahida loo qabo soo saaraha. Caadi ahaan, kaneecada ayaa ah milix metal ah. Kuwa ugu caansan waa manganis (II) fluoride ama cadmium (II) fluoride, inkastoo xeryahooda thallium iyo cobalt ay noqon karaan kuwo bedelaad ah.
  5. Pyridine waxaa laga soo celiyaa alaabooyinka ayadoo loo marayo geeddi-socodka badan. Qeyb ka mid ah xaddiga ugu weyn ee Chichibabin pyridine synthesis waa soodirkiisu hooseeyo, tarjumo ku saabsan 20% alaabta dhamaadka. Sababtan awgeed, qaababka aan la daboolin ee dhismahaani way ka sii yar yihiin.

Duufaan Bönnemann

Duufaan Bönnemann waa qaabka loo yaqaan 'trimer' oo ka soo jeeda laba qaybood oo ah molecule acetylene iyo qeyb ka mid ah nitrile. Dhab ahaantii, geeddi-socodku waa isbeddel lagu sameeyo jilitaanka reppe.

Farsameyntu waxay fududeyneysaa kuleylka heerkulka sare iyo cadaadiska ama iyada oo loo marayo cyclingdition photo. Marka firfircooni ku shaqeynayo, Bönnemann cyclization waxay u baahan tahay CoCp2 (Cyclopentadienyl, 1,5-cyclooctadiene) si ay u dhaqmaan sida xayawaan.

Habkani wuxuu soo saari karaa silsilad ah pyridine derivatives ku xiran tahay xeryahooda loo isticmaalo. Tusaale ahaan, acetonitrile waxay dhalinaysaa 2-methylpyridine, taas oo ku dhici karta dealkylation si loo sameeyo pyridine.

Hababka kale

Qodobka Kröhnke Pyridine

Habkani wuxuu isticmaalaa pyridine sida reagent, inkasta oo aan lagu darin badeecad dhamaadka ah. Contrary, dareen-celinta ayaa abuuri doonta pyridines la beddelay.

Markii la falceliyo α-bromoesters, pyridine waxay qaadan doontaa falcelin Michael ah oo leh maadooyinka karantiilka ee aan habboonayn si loo sameeyo bedelka pyridine iyo pyridium bromide. Dareenka waxaa lagu daaweeyaa ammonia acetate gudaha 20-100 ° C xaalado sahlan.

Dib-u-habaynta Ciyaalka-Dennstedt

Tani waxay keenaysaa in giraanta-fidinta pyrrole leh dichlorocarbene oo sameysma 3-chloropyridine.

Qalabka Gattermann-Skita

Dareenkan, milixda cusbada ee milonat-ku wuxuu kujiraa dichloromethylamine iyadoo ay joogaan saldhig.

Soodhaweynta Bogiraha Bogirta

Falcelinta pyridines

Dareen-celinnada soo socda ayaa loo saadaalin karaa inay yihiin pyridines-ka qaab-dhismeedka elektarooniga ah:

  1. Heteroatomku wuxuu sameeyaa pyridines si aad ah oo aan u adkeynin habka caadiga ah ee bedelka qalabka korantada (electrophilic aromatic). Taa bedelkeeda, pyridines waxay u nugul yahiin weerarka nukleophilic. Pyridines waxay ku dhacaan falcelinta beddelidda elektrofiliciga (SEAr) oo aad u xiiseynaya, laakiin badalaadda nucleophilic (SNAr) oo ka badan baasiin.
  2. Xakamaynta farsamoyinka "electrophilic" waxay doorbidaan Natom iyo bc-atoms, halka reagentiyada nucleophilic ay doorbidaan a- iyo cC-atoms.

Iskudhin dheeri ah ee kudheerka ah Nitrogen

Dareen-celinta oo ku lug leh samaynta isku-xirnaanta iyadoo la isticmaalayo labada lafo ee electrons ee nitrogen-ga, sida kor u-qaadista iyo quaternization, pyridines waxay u dhaqmeysaa sida ambalaasta jilicsan ama aminaha.

Marka a pyridine ka soo horjeedo saldhig ama nucleophile, waxay samaysaa ciriiri pyridinium ah kaas oo sextet saliideed la sii haynayo, iyo nitrogen waxay qaadataa ganaax rasmi ah.

Ilaalinta Nitrogenka

Pyridines waxay sameeyaan crystalline, marar badan hygroscopic, cusbada leh asiidhka ugu badan.

Nitrateeynta Nitrogen

Tani waxay u dhacdaa si dhakhso ah oo ay uga jawaabto fal-celinta pyridines leh cusbada nitronium, sida nitronium tetrafluoroborate. Walxaha nukliyeerka ah sida nitric acid, dabcan, waxay u horseedaa N-protonation.

Xasilinta at nitrogen

Chlorides acids iyo acylsulfonic acids ay si dhakhso ah u falcelinayso pyridines soo saara 1-acyl- iyo 1-arylsulfonylpyridinium cusbada xalka.

Halista alkylil iyo sulfates waxay si fudud ula falgalaan pyridines siinta cusbada pyridinium kuatada.

Kala beddelashada Nucleophilic

Si ka duwan benzene, siyaado badan oo nucleophilic ah waxay noqon kartaa mid firfircoon oo si wax ku ool ah ay u joogteeyaan pyridine. Sababtoo ah giraantu waxay leedahay cufnaan yar oo elektaroonik ah oo ka kooban jajabyo. Waxyeellada waxaa ka mid ah bedelo leh ka kaxayntu ay of ra'iyi ah hydride iyo tirtiridda-daro si aad u hesho ah qaabeynta aryne dhexe oo inta badan ay sii wadaan 2- ama 4-meel.

Pyridine kaligeed ma keeneyso in la sameeyo isbeddel nucleophilic dhowr ah. Si kastaba ha ahaatee, isbeddelka pyridine leh bromiin, qaybaha sulfonic acid, chlorine, iyo fluorine waxay keeni kartaa koox goynta ah. Sameynta maadooyinka organolithium waxaa laga soo celin karaa kooxda ugu fiican ee ka tagta fluorine. Cadaadiska sare, nucleophilic wuxuu wax ka qaban karaa alkoxidyada, qanjirada, amin, iyo xeryaha ammonia.

Tiro yar heterocyclic dareen-celin ayaa dhici karta sababtoo ah adoo isticmaalaya koox sabool ah oo baxsan sida hydride iyio. Pyridine derivations at 2-booska waxaa laga heli karaa iyada oo loo marayo falcelinta Chichibabin. 2-aminopyridine wuxuu sii wadi karaa gaari marka sodyam amid loo isticmaalo nucleophile. Maaddooyinka hydrogen ayaa la sameeyaa marka ay protons ka dhigaan kooxda amaba ay isku daraan iyadoon hideen.

Sidoo kale benzene, pyridines dhexdhexaadinta sida heteroaryne waxaa laga heli karaa iyada oo loo marayo beddelada nucleophilic si aad u hesho pyridine. Isticmaalka alkolada adag sida sodium iyo potassium tert-butoxide waxay ka caawin kartaa in laga takhaluso dheecaannada pyridine markay isticmaalayaan midigta ka baxsan kooxda. Ka dib marka la hirgeliyo nucleophile ee cirbadda saddexlaha ah, waxay hoos u dhigtaa doorashooyinka waxayna horseedi doontaa samaynta isku dhaf ah oo leh laba waxyaalood oo suurtagal ah.

Beddelaadda Electrophilic

Dhowr pyridine electrophilic soodejinta waxay sii wadi kartaa ilaa heer dhibco ama ma sii wadaan gebi ahaanba. Dhinaca kale, elementka heteroaromatic waxaa lagu kicin karaa iyada oo loo marayo farsameynta qalabka elektarooniga ah. Aaladda alaabooyinka "Friedel-Crafts" (furfuran) waa tusaale ka mid ah alkylations and acylations. Aragtidu waxay ku guuldareysatey in ay maraan pyridine tan iyo markii ay keento in lagu daro atomiga nitrogen. Beddelaaddu waxay inta badan ku dhacaan saddexda jago, kuwaas oo ka mid ah jumlado yaryar oo caarad ku jira oo ku yaala giraanta, taas oo u dhiganta isku dhafka elektrofurka.

Qaabdhismeedka Pyridine N-Oxide

Beddelka elektaroonigga ah wuxuu keeni karaa isbeddelka booska pyridine ee 2- ama 4-booska sababtoo ah fal-celin xeeldheer oo xasaasiga ah. Si kastaba ha ahaatee, habab tijaabo ah ayaa loo isticmaali karaa marka la samaynayo bedelaadda elektrofiliciga ah ee pyridine N-oxide. Waxaa markaa la socda daadinta nitrogen-ka ee xashiishka. Sidaa daraadeed, hirgelinta ogsijiinta waxaa lagu yaqaanaa in ay hoos u dhigto cufnaanta nitrogen isla markaana sii xoojinta bedelka 2-ka iyo xarumaha 4.

Noocyada maadada daawada qaaliga ah ama fosfooraska xaraashka ah waxaa lagu yaqaanaa in si sahlan loo isticmaalo oxidised inta badan loo isticmaalo in laga saaro atomka oksijiinka. Oxfermine oxygen oxide waa maaddo la sameeyay ka dib markii oxidation of Reaction Trifenylphosphine. Waa shey kale oo loo isticmaali karo in laga takhaluso aaladda oksijiinta oo ka soo jeeda kale. Macluumaadka hoos ku qoran wuxuu sharaxayaa sida bedelka caadiga ah ee elektrofiliciga ah uu ka soo horjeedo pyridine.

Nitrical Direct Pyridine wuxuu u baahan yahay xaalado adag oo adag, guud ahaanna wuxuu leeyahay wax yar. Ficil-celinta xayawaanka Pitoxide dinitrogen leh pyridine iyadoo joogitaanka sodium waxay keeni kartaa sameynta 3-nitropyridine. Wershadaha ku jira pyridine waxaa lagu heli karaa iyada oo loo marayo nitration of nitronium tetrafluoroborate (NO2BF4) adoo ka soo qaadaya aaladda nitrogen ee nadiif ah iyo elektaroonik ahaan. Qodobbada laba xeryood ee 6-dibromo pyridine waxay keeni kartaa samaynta 3-nitropyridine ka dib marka laga saaro atomi bromine ah.

Nitrate toos ah ayaa loo tixgeliyaa inuu yahay mid ka raaxo badan marka laga eego sulfonation of pyridine. Karkarinta pyridine at 320 ° C waxay keeni kartaa in pyridine-3-sulfonic acid ka dhaqsiyo badan karkaridda sulfuric acid heerkulka isla. Qodobka kudheerka ah ee kudubka ah ee nitrogen-yada waxaa laga heli karaa by jawaab celinta SO3 ee joogitaanka mercury (II) sulfate taas oo u dhaqmeysa sidii xayiraad.

Chlorination-ka iyo bromination-ku wuxuu sii wadi karaa si ka duwan sida naadiyaha iyo sulfonation. 3-bromopyridine waxaa laga heli karaa iyada oo loo eegayo falcelinta kiniiniga molecular ee sulfuric acid at 130 ° C leh pyridine. Marka koloriin lagu daro, natiijada 3-chloropyridine waxay noqon kartaa mid hooseeya iyada oo ay joogaan chloride aluminium taasoo u dhaqanta sida xajinimada 100 ° C. Fal-celinta tooska ah ee halogen iyo palladium (II) waxay keeni kartaa labadaba 2-bromopyridine iyo 2-chloropyridine.

Isticmaalka Pyridine

Mid ka mid ah alaabta ceeriin ee muhiim u ah warshadaha kiimikada waa pyridine. 1989, wax soo saarka guud ee pyridine adduunka wuxuu ahaa 26K tonnes. 1999, 11 ka baxsan 25 goobaha wax soo saarka ee ugu weyn ee Pyridine ayaa ku yaala Yurub. Badeecadaha waaweyn ee pyridine waxaa ka mid ah Koei Chemical, Industries Chemical, iyo Evonik Industries.

2000sii hore, wax soo saarka pyridine wuxuu kordhay heer sare. Tusaale ahaan, dalka Shiinaha oo keli ah ayaa ku dhuftey wax soo saarka sanadlaha ah ee 30,000 tan. Maanta, wadashaqeyn dhexmarta Maraykanka iyo Shiinaha waxay keenaysaa waxsoosaarka ugu sareeya ee pyridine.

Cayayaanka

Pyridine waxaa badanaa loo isticmaalaa sidii horey loogu talagalay laba diirad oo loo yaqaan 'herbicides' iyo 'ragquat'. Diyaarinta fangasiga ku salaysan pyrithione, pyridine waxaa loo isticmaalaa sida aasaaska aasaasiga ah.

Dareenka u dhexeeya Zincke iyo Pyridine waxay keenaysaa soo saarida laba qaybood - laurylpyridinium iyo cetylpyridinium. Iyada oo ay ku xiran yihiin hantidooda antiseptic, labada xeryood ayaa lagu daraa alaabta daryeelka ilkaha iyo afka.

Weerar by wakiil alkylating si pyridine waxay keentaa in cusbada N-alkilpyridinium, chloride cetylpyridinium hal tusaale ah.

Paraquat Synthesis

Xallil

Codsi kale oo loo isticmaalo pyridine waa kondhom Knoevenagel, taas oo loo adeegsanayo habka hooseeya, dabayl, iyo dareeraha aasaasiga ah. Pyridine si gaar ah ugu fiican ee dehalogenation, halkaas oo ay u adeegto sida salka reaction hareen halka lagala kulmo halide ah hydrogen sababtay in ay sameeyaan cusbo pyridinium.

Xilliyada maqalka iyo qiimeeynta, Pyridine wuxuu hawlgeliyaa anhydrides ama halista karboksilic acid. Xitaa xitaa firfircoon ee fal-celintaasi waa 4- (1-pyrrolidinyl) pyridine iyo 4-dimethylaminopyridine (DMAP), oo ah noocyada pyridine. Dareenka kicitaanka, Pyridine waxaa caadi ahaan loo isticmaalaa saldhig.

Abuuritaanka pyridinium iyada oo loo marayo fal-celinta la tirtiro leh pyridine

Pyridine sidoo kale waa walax cayriin oo muhiim ah ee warshadaha dharka. Ka sokow in loo isticmaalo sidii xal wax ku ool ah ee soo saarida caag iyo dhaylo, waxa kale oo loo adeegsadaa in lagu xoojiyo awoodda shabakada.

Maamulka Cuntada iyo Dawooyinka ee Mareykanka ayaa ansixiyay dheellitirka pyridine yar ee cuntooyinka yaryar si loo siiyo cunto dhadhan qadhaadh ah.

Xalalka, xaddiga ogaanshaha pyridine waa agagaarka 1-3 mmol·L-1 (79-237 mg · L-1). Ahaanshaha saldhig, pyridine waxaa loo isticmaali karaa sida Karl Fischer. Si kastaba ha ahaatee, imidazole waxaa badanaa loo isticmaalaa beddelka pyridine sida (imidazole) uu leeyahay ur wacan.

Diyaargarawga Piperidine

Xakamaynta Pyridine oo leh ruthenium-, cobalt-, ama nikkel-ku salaysan xajmiga heerkulka sare waxay keenaysaa soo saarista piperidiin. Tani waa nadaafad hetogoog ah oo muhiim ah oo ah dhismo muhiim ah oo loo yaqaan 'synthetic building block.

Reagelinta Gaarka ah ee ku Saleysan Pyridine

1975, William Suggs iyo James Corey waxay sameeyeen chlorochromate pyridinium. Waxaa loo adeegsadaa in lagu sifeeyo alkolada labaad ee ketones iyo khamriga hoose ee aldehydes. Chlorochromate Pyridinium waxaa sida caadiga ah la heli karaa markii pyridine lagu daro xalka of hydrochloric iyo chromic acid concentrate.

C5H5N + HCl + CrO3 → [C5H5NH] [CrO3Cl]

Iyada oo chloryl chloride (CrO2Cl2) oo ah kansaroji, jid kale oo loo baahan yahay in la raadsado. Mid ka mid ah waa in la isticmaalo chloride pyridinium si loo daaweeyo chromium (VI) oxide.

[C5H5NH+] Cl- + CrO3 → [C5H5NH] [CrO3Cl]

Sarret Reactent (kakooban ee chromium (VI) oxide oo leh pyridine heterocycle ee pyridine), pyridinium chlorochromate (PCC), Reagent Cornforth (pyridinium dichromate, PDC), iyo Collins reagent (kakabka chromium (VI) oxide leh pyridine heterocycle ee dichloromethane) waa xeryahooda chromium-piridin. Waxay sidoo kale codsadeen oksaydhka, sida beddelidda khamriga hoose iyo tan koowaad ee ketones.

Reer Reer Sarah iyo Collins ma aha oo kaliya inay isku diyaariyaan, laakiin sidoo kale waxay halis u yihiin. Waxay yihiin hygroscopic waxayna u nugul yihin in la iska daayo waqtiga geedi socodka. Sidaa darteed, isticmaalka PDC iyo PCC ayaa lagu taliyay. Inkastoo labadii qaybood oo si weyn loo isticmaalay 70s iyo 80s, haddana marar dhif ah ayaa loo adeegsadaa iyadoo sababtuna tahay sarkooda iyo in la xaqiijiyo kansarku.

Qaabdhismeedka curiyaha Crabtree

Isku-dubaridka kiimikada, pyridine waxaa si weyn loo isticmaalaa lafta. Waa derivative, sida ay tahay 2,2'-bipyridine, oo ka kooban maaddooyinka lirir 2 ku lifaaqan curaarta keliya, iyo terpyridine, oo ah molecule oo ah siddeed pyridine oo isku xiran.

Saldhig xooggan oo Lewis ah ayaa loo isticmaali karaa beddelka lidka aaladda pyridine oo qayb ka ah dhismo bir ah. Dabeecaddan waxaa loo adeegsadaa catalysis ee polymerization iyo falcelinta hydrogenation, iyadoo la adeegsanayo, tusaale, Carabtree's catalyst. Pyridine Lingard in la beddelo inta lagu guda jiro fal-celinta ayaa dib loo soo celiyaa kadib markii la dhammeeyo.

tixraacyada

Nomenclature of Chemistry Organic: Talooyinka IUPAC iyo Magacyada La Qaadey 2013 (Buugga Blue). Cambridge: Jaamacadda Boqortooyada ee Kimistaanka. 2014. p. 141.

Anderson, T. (1851). "Ueber Dhimasho Dhibaato" Trailing thierischer Materien "[Waxyaabaha qalalan ee qalalanaanta xayawaanka]. Annalen der Chemie und Pharmacie. 80: 44.

Sherman, AR (2004). "Pyridine". Paquette, L. Ansixinta 'Reagents for Synthesis'. e-EROS (Encyclopedia of Reagents for Synthesis). New York: J. Wiley & Wiilasha.

Behr, A. (2008). Cuntada loo yaqaan 'Angewandte homogene Katalyse'. Weinheim: Wiley-VCH. p. 722.