6.3.2 Spectroscopy. N Goalby chemrevise.org 1 NO 2 CH 3. CH 3 C a. NMR spectroscopy. Different types of NMR

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1 6.. Spetrosopy NMR spetrosopy Different types of NMR NMR spetrosopy involves intertion of mterils with the lowenergy rdiowve region of the eletromgneti spetrum NMR spetrosopy is the sme tehnology s tht used in mgneti resonne imging (MRI) to otin dignosti informtion out internl strutures in ody snners There re two min types of NMR. NMR. (proton) NMR There is only round % in orgni moleules ut modern NMR mhines re sensitive enough to give full spetr for The spetr is simpler spetrum thn the NMR Equivlent ron toms. In NMR spetrum, there is one signl (pek) for eh set of equivlent toms. d peks 4 peks, dinitroenzene, dinitroenzene,4 dinitroenzene N peks N 4 peks peks d 4 peks peks l d peks d e N 5 peks N Goly hemrevise.org

2 Equivlent ydrogen toms. In n NMR spetrum, there is one signl for eh set of equivlent toms. Ethnol hs groups of different hydrogen toms sets of equivlent s: rtio ::9 sets of equivlent s: rtio :: In ddition the intensity (integrtion vlue) of eh signl is proportionl to the numer of equivlent toms it represents. Br d d d 4sets of equivlent s: rtio 6::: signl sets of equivlent s: rtio :: 4 sets of equivlent s: rtio ::: d Solvents Smples re dissolved in solvents without ny toms, e.g. l 4, Dl. This mens tht in the NMR the solvent will not give ny peks The sme solvent is used in NMR nd in this se there will e one pek due to the solvent tht will pper on the spetrum. owever, it is known where this pek is so it n e ignored. In the exm it is likely this pek will not our on the spetr. lirtion nd shift A smll mount of TMS (tetrmethylsilne) is dded to the smple to lirte the spetrum TMS is used euse: its signl is wy from ll the others it only gives one signl it is non-toxi it is inert it hs low oiling point nd so n e removed from smple esily Si tetrmethylsilne The sme lirtion ompound is used for oth nd NMR The spetr re reorded on sle known s the hemil shift (δ), whih is how muh the field hs shifted wy from the field for TMS.. The δ is mesure in prts per million (ppm) is reltive sle of how fr the frequeny of the proton signl hs shifted wy from tht for TMS δ hemil shift (ppm) 0 N Goly hemrevise.org

3 NMR shift The δ depends on wht other toms/groups re ner the more eletronegtive groups gives greter shift. δ ppm Proton exhnge using D δ ppm If D is dded to smple then proess of proton exhnge hppens with the in ny - nd N- onds. This hs the effet of removing the peks from the - NMR spetr. This n help with the identifition of nd N peks on the spetr. Addition of D to the smple of Propnoi id would mke the pek t δ =.7 (ppm) in the ove spetrum dispper N Goly hemrevise.org

4 NMR shift Spin-Spin oupling in NMR In high resolution NMR eh signl in the spetrum n e split into further lines due to inequivlent s on neighouring toms. ppm Nulei in identil hemil environments do not show oupling mongst themselves! Splitting of pek = numer of inequivlent s on neighouring toms + signl singlet doulet triplet qurtet quintet pperne Split numer of peks numer of neighouring inequivlent toms reltive size : :: ::: :4:6:4: The pek due to group will e triplet s it is next to ( ron with s) The pek due to group will e qurtet s it is next to ( ron with s) The pek due to group will e singlet s it is next to ron with no s) For 6 split peks use the term hextet or multiplet The pek due to group will e triplet s it is next to ron with s Shift Integrtion tre The pek due to group will e singlet s it is next to ron with 0 s Shift.-.6 Integrtion tre The pek due to group will e qurtet s it is next to ron with s Shift.7-4. Integrtion tre ppm N Goly hemrevise.org 4

5 Infrred spetrosopy ertin onds in moleule sor infr-red rdition t hrteristi frequenies using the ovlent onds to virte ABVE 500 m - Funtionl group identifition omplited spetr n e otined thn provide informtion out the types of onds present in moleule BELW 500 m - Fingerprinting omplited nd ontins mny signls piking out funtionl group signls diffiult. This prt of the spetrum is unique for every ompound, nd so n e used s "fingerprint". e.g. = m - - (id) m - Use n IR sorption tle provided in exm to dedue presene or sene of prtiulr onds or funtionl groups Bond Wvenumer A omputer will ompre the IR spetr ginst dtse of known pure ompounds to identify the ompound use spetr to identify prtiulr funtionl groups limited to dt presented in wvenumer form e.g. n lohol from n sorption pek of the ond, = roxyli ids Very rod N Aohols, phenols rod Spetr for utnl = Asorption or trough in etween m - rnge indites presene of = ond Alwys quote the wve numer rnge from the dt sheet - sorptions tend to e rod Asorption or trough in etween m - rnge indites presene of - ond in n id Spetr for ethnoi id Modern rethlysers mesure ethnol in the reth y nlysis using infrred spetrosopy = N Goly hemrevise.org 5

6 Mss spetrometry Mesuring the M r of n orgni moleule Spetr for 4 0 If moleule is put through mss spetrometer it will often rek up nd give series of peks used y the frgments. The pek with the lrgest m/z, however, will e due to the omplete moleule nd will e equl to the M r of the moleule. This pek is lled the prent ion or moleulr ion Mss spetrum for utne Moleulr ion Frgmenttion When orgni moleules re pssed through mss spetrometer, it detets oth the whole moleule nd frgments of the moleule. Moleulr ion formed: M [M] +. + e The moleule loses n eletron nd eomes oth n ion nd free rdil Severl peks in the mss spetrum our due to frgmenttion. The Moleulr ion frgments due to ovlent onds reking: [M] +. X + + Y. Reltively stle ions suh s rotions R + suh s + nd ylium ions [R-=] + re ommon. The more stle the ion, the greter the pek intensity. This proess produes n ion nd free rdil. The ion is responsile for the pek The pek with the highest mss/hrge rtio will e normlly due to the originl moleule tht hsn t frgmented (lled the moleulr ion). As the hrge of the ion is + the mss/ hrge rtio is equl to Mr. Mss spetrum for utne = 58 Eqution for formtion moleulr ion 4 0 [ 4 0 ] +. + e m/z 58 Equtions for formtion of frgment ions from moleulr ions [ 4 0 ] +. [ ] + +. m/z 4 [ 4 0 ] +. [ ] + +. m/z 9 Mss spetrum for utnone The high pek t 4 due to stility of yl group 4 [ ] + Eqution for formtion moleulr ion [ ] +. + e m/z 7 Equtions for formtion of frgment ions from moleulr ions [ ] +. [ ] + +. m/z 57 9 [ ] + [ ] + 57 [ ] +. 7 [ ] +. [ ] + +. m/z 4 [ ] +. [ ] + +. m/z 9 N Goly hemrevise.org 6

7 Bringing it ll together. Work out empiril formul Elementl nlysis 66.6%.8%.9%. Using moleulr ion pek m/z vlue from mss spetrum lulte Moleulr formul moleulr ion pek m/z vlue= /.8/.9/6 =5.555 =.8 = =4 =8 = Mr empiril formul 4 8 = 7 If Mr moleulr formul 44 then ompound is 8 6. Use IR spetr to identify min onds/funtionl group 8 6 ould e n ester, roxyli id or omintion of lohol nd ronyl. Look for IR spetr for = nd - onds There is = ut no - sorptions, so must e n ester. - = 4. Use NMR spetr to give detils of ron hin 4 peks only 4 different environments. singlet of re 9 At δ =0.9 Mens groups 9 Pek t δ 4 shows Are suggests Qurtet mens next to Pek t δ. shows = Are suggests Singlet mens djent to with no hydrogens Pek t δ. shows R- Are mens Triplet mens next to 5 4 δ ppm Put ll together to give finl struture N Goly hemrevise.org 7

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