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- Ἐπαφρόδιτος Μπλέτσας
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1 Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2015! Synthesis)and)characterisation)of)an)open1cage) fullerene)encapsulating)hydrogen)fluoride! Supplementary!Information! Experimentalprocedurescompoundcharacterizationdataanddetailsofcalculations. A.KrachmalnicoffR.BoundsS.MamoneM.H.LevittM.CarravettaandR.J.Whitby* *ChemistryUniversityofSouthamptonSouthamptonSO171BJUK TABLE!OF!CONTENTS:! General!Materials!Solution!NMR!Solid8state!NMR...page!1! Simulations!and!DFT!calculations!...page283! References...page!9! ) )
2 General:!! All!reactions!were!executed!under!nitrogen!atmosphere.!All!additions!were!performed! using!regular!air8free!techniques.!reactions!involving!hydrogen!fluoride!pyridine!were! carried! out! in! polytetrafluoroethylene! (PTFE)! or! polyethylene! (PE)! tubes! fitted! with! screw!caps.!hydrogen!fluoride!pyridine!was!handled!using!pe!or!ptfe!containers!and! tubing.!the!reaction!course!was!monitored!by!tlc!using!merck!silica!gel!60!f254!plates! detecting!the!spots!using!an!uv!lamp!or!by!hplc!performed!on!a!cosmosyl!bukyprep! analytical! column! with! detection! at! 326nm.! Flash! column! chromatography! was! run! using!merck!silica!gel!geduran!si60!(40863!μm)!as!stationary!phase.!ft8ir!spectra!were! recorded! on! a! Bruker! Alpha8T! instrument.! UV8Vis! spectra! were! recorded! on! an! Ocean! Optics!USB2000+!UV/Vis!spectrometer.!Electrospray!mass!spectra!were!recorded!in!the! positive!ion!mode.!the!expected!peaks!due!to!natural!abundance!of! 13 C!were!present! but!not!reported.!note!that! due! to! the! noise! reducing! threshold! used! in! processing! relative!intensities!of!weak!peaks!are!reduced.! Materials:) Compound!1!was!synthesised!according!to!the!reported!procedure. 1!Dichloromethane! was! distilled! over! calcium! hydride! under! nitrogen! atmosphere.! 70%! w/w! hydrogen! fluoride!in!pyridine!was!purchased!from!sigma8aldrich!company!ltd.!and!directly!used! as!supplied.!! Solution)NMR:) Spectra! were! recorded! on! Bruker! DPX400! or! 500! spectrometers.! Chemical! shifts! are! reported!in!ppm!and!referenced!to!the!residual!solvent!peak!for! 1 H!and! 13 C!or!CFCl3!for! 19 F!spectra.) Solid1State)NMR:) 1 H! NMR! Experiments! were! performed! at! 20! T! (850! MHz)! at! the! National! High! field! facility! at! the! University! Of! Warwick! on! a! Bruker! AVANCE! III! console.! A! Hahn! echo! experiment! with! a! 92! KHz! amplitude! pulse! was! used! to! generate! the! transverse! magnetization!and!a!dead!time!of!5!µs!was!left!before!recording!the!free!induction!decay.! The! spectrum! is! the! average! of! 8! transients! with! 4! seconds! between! scans.! The! 1
3 experiments!were!performed!using!magic!angle!spinning!at!variable!spinning!speeds!to! remove!anisotropic!interactions!and!increase!resolution.! 1 H!proton!NMR!spectra!were! referenced!to!adamantane!at!1.8!ppm. 2! 19 F!experiments!were!also!performed!at!20!T!the!spectra!are!the!result!of!256!scans! with!a!2!second!pulse!delay.! 19 F!spectra!were!referenced!to!β8Polyvinylidene!fluoride! (PVDF)!as!an!indirect!reference!for!the!accepted!0!ppm!IUPAC!standard!CFCl3(aq)!with! a!chemical!shift!of!898!ppm. 2!To!protect!the!sample!against!heat!generated!from!high! spinning! speeds! a! nitrogen! gas! stream! was! used! for! cooling! at! speeds! of! 20! KHz! and! above.!processing!of!spectra!was!done!using!matnmr.! Simulations:! In! order! to! extract! NMR! interaction! parameters! we! used! SPINACH 34! for! global! minimization!with!multiple!experimental!datasets.!then!we!verified!error!margins!with! SIMPSON 5! by! simulating! a! matrix! of! various! interaction! magnitudes! and! monitoring! RMS!between!experiment!and!simulations!centered!around!the!best!fit!values.! DFT)calculations:) Density!Function!Theory!calculations!on!the!formation!of!H2@2B!H2O@2B!and!HF@2B! where!2b!is!a!model!for!2!in!which!the!58tert8butyl8pyridyl!substituents!were!replaced! by! methyl! groups! were! carried! out! using! Guassian! 09 6! and! the! results! are! shown! in! Table! 1.! Minimum! energy! and! transition! state! structures! were! obtained! using! the! B3LYP!functional 7!with!6831G(d)!basis!set. 8!Frequency!calculations!were!carried!out!to! confirm!the!nature!of!the!structures!(single!imaginary!frequency!for!transitions!states)! and!to!provide!a!zero!point!energy!correction.!energies!were!obtained!by!single!point! calculations! using! Truhlar s! MO62X! hybrid! functional! (which! copes! well! with! dispersion8like! interactions) 9! with! Dunning s! cc8pvdz! correlation! consistent! double8 zeta!basis!set 10!correcting!for!Basis!Set!Superposition!Errors!using!counterpoise. 11!Note! that! B3LYP! gives! poor! results! as! would! be! expected! for! a! functional! which! neglects! dispersion8like!interactions.!!!! 2
4 Table&1."Calculations"on"activation"energy"for"entry"/"exit"and"binding"energy"for"H2"H2O"and"HF"into&2B." " Energies(/(Hatree( ( ( ( ( ( ( ( ( ( ( H 2 # 2B# zpe( H 2 ( zpe( H cp( zpe( TS( cp( zpe( B3LYP/631d( < ( ( < ( ( < ( ( ( < ( ( ( m062x/vdz@b3lyp/631d( < ( ( < ( ( < ( ( ( < ( ( ( H 2 O# 2B# zpe( H2O( zpe( H2O@2B( cp( zpe( TS( cp( zpe( B3LYP/631d( < ( ( < ( ( < ( ( ( < ( ( ( m062x/vdz@b3lyp/631d( < ( ( < ( ( < ( ( ( < ( ( ( HF# 2B# zpe( HF( zpe( HF@2B( cp( zpe( TS( cp( zpe( B3LYP/631d( < ( ( < ( ( < ( ( ( < ( ( ( m062x/vdz@b3lyp/631d( < ( ( < ( ( < ( ( ( < ( ( ( " # Energies(/(Hartree( Energies(/(kJ/mol( H2# E(H 2 +2B))( Ea((entry)( Ea((exit)( E(H 2 +2B))( Ea((entry)( Ea((exit)( B3LYP/631d( ( ( ( 14.87( 84.38( 69.51( m062x/vdz@b3lyp/631d( < ( ( ( <21.01( 64.32( 85.33( H2O# E(H 2 O@2B<(H 2 O+2B))( Ea((entry)( Ea((exit)( E(H 2 O@2B<(H 2 O+2B))( Ea((entry)( Ea((exit)( B3LYP/631d( ( ( ( 18.04( ( 92.77( m062x/vdz@b3lyp/631d( < ( ( ( <39.89( 52.22( 92.11( HF# E(HF@2B<(HF+2B))( Ea((entry)( Ea((exit)( E(HF@2B<(HF+2B))( Ea((entry)( Ea((exit)( B3LYP/631d( ( ( ( 8.89( 74.33( 65.44( m062x/vdz@b3lyp/631d( < ( ( ( <25.91( 29.84( 55.75( " cp">"counterpoise"correction"for"basis"set"superposition"error" zpe">"zero"point"energy"correction"(taken"from"b3lyp/631d"frequency"calculation)." TS" "Transition"state"of"entry/exit"of"the"endohedral"molecule." 3"
5 Compound! 1) (316! mg! 0.282! mmol)) was! placed! inside! an! oven! dried! polytetrafluoroethylene!(ptfe)!tube!equipped!with!a!screw!cap.!the!tube!was!flushed! with!nitrogen!gas!and!distilled!dichloromethane!(16!ml)!was!added!under!nitrogen!gas.! 70%!w/w!hydrogen!fluoride!in!pyridine!(1.5!mL!205!eq!of!HF)!was!added!and!the!tube! was! closed.! The! mixture! was! stirred! at! room! temperature! for! 23! hours.!the!reaction! was!quenched!by!dropping!it!via!ptfe!tubing!inside!a!round!bottom!flask!containing! Na2CO3! saturated! solution! (50! ml)! and! toluene! (50! ml)! under! stirring.! After! the! evolution!of!gas!had!stopped!the!organic!layer!was!collected!washed!with!brine!dried! over!mgso4!filtered!and!evaporated!to!dryness!to!afford!a!black!solid.!this!material!was! purified! by! flash! column! chromatography! over! silica! gel! (eluent! gradient!5%! to! 15%! ethyl!acetate!in!toluene).!the!fractions!containing!the!spot!located!at!rf!=!0.31!(eluent! as!a!black!solid!(283!mg!89%).! 1 H)NMR!(400!MHz!CDCl3!δ):!7.64!(t!J!=!7.8!Hz!1H!H84!of! pyridyl)!7.57!(t!j!=!7.8!hz!1h!h84!of!pyridyl)!7.49!(dd!j!=! 7.5!2.2!Hz!1H!H83!or!H85!of!pyridyl)!7.23!(d!J!=!7.8!Hz! 1H!H83!or!H85!of!pyridyl)!7.22!(d!J!=!7.8!!Hz!1H!H83!or! H85! of! pyridyl)! 7.17! (d! J! =! 7.7! Hz! 1H! H83! or! H85! of! pyridyl)!7.12!(d!j!=!10.2!hz!1h!alkenyl)!7.02!(d!j!=!10.1! Hz!1H!alkenyl)!6.28!(s!broad!1H!hydroxyl)!6.00!(s!broad!1H!hydroxyl)!1.24!(s!9H!t8 butyl)!1.18!(s!9h!t8butyl)!86.55!(d!j!=!508!hz!0.5!h!endohedral!hf).) Note:!the!signals!of!the!H83!or!H85!protons!of!the!pyridyl!groups!falling!between!7.25! and!7.15!ppm!overlapped!with!the!aromatic!ch!signals!from!residual!toluene!present!in! the!sample.!prolonged!exposure!of!the!sample!to!high!vacuum!(>0.1!mmhg)!to!achieve! complete!removal!of!residual!toluene!led!to!a!substantial!loss!(850%)!of!the!endohedral! HF.! 13 C) NMR:) (125! MHz! odcb8d4! δ):! ! ! ! ! ! ! !164.42!162.84!153.56!149.94!149.56!149.5!148.47!148.39!147.78!147.63! !147.04!146.69!146.15!145.21!145.16!144.96!144.42!143.61!143.48!142.96! 4
6 142.57! ! ! ! ! ! ! 140! ! ! 138.2! 137.5! ! ! ! ! ! ! ! ! 134.3! ! !131.98!131.45!131.3!129.02!119.99!119.86!117.45!117.42!116.86!116.83! !96.97!59.75!59.72!54.87!37.65!37.46!29.94!29.8.! Note:! the! solvent! signals! overlapped! between! 132.3! and! 128.8! ppm.! The! signals! of! compound!1!are!present!but!not!listed.! 19 F)NMR:)(376!MHz!CDCl3!δ):! !(d!J!=!508!Hz).) { 1 H} 19 F)NMR:)(376!MHz!CDCl3!δ):! !(s).) IR:!(ν!cm81):!3445!2958!1761!1694!1571!1515!1444!1145!1080.) UV:!CH2Cl2!λmax!(ε):!258.60!(92550)!327.93!(36421).! MS1ESI:!m/z!(relative!intensity!ion):!1141!(100%![M+H] +!HF@1)!1121!(53%![M+H] +! empty!1)! 1HNMR.esp 1HNMR.esp CHCl3 CHCl HNMR.esp Toluene Water H)NMR)spectrum)of)compound)HF@1.)) 5
7 ) 19 F)NMR)spectrum)of)compound)HF@1.)!! {1H}19FNMR.esp { 1 H} 19 F)NMR)spectrum)of)compound)HF@1.)) 6
8 13CNMR.esp odcb-d C) ) ) ) Transmittance [%] Wavenumber cm-1 IR)spectrum)of)compound)HF@1.)) 7 Page 1/1
9 ) 8
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