仪器——课件HNMR幻灯片.pptVIP

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仪器——课件HNMR幻灯片.ppt

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20 1 22 23 1 1 6 6 1 * * * * * * * * * * * * * * * * * 6 1 15 15 15 21 21 21 21 21 21 * * * * * * * * 25 3 7 7 10 11 9 1 1 19 19 19 19 dd J=7.7, 1.5 dd J=8.1, 0.7 td J=7.4, 1.1 ~td J=8.1, 1.5 Aromatic substituent pattern 1 Calculated shifts ?1 = 8.31 ?2 = 7.74 ?1 = 7.69 ?1 = 8.08 C5H9NO4 1H 2H 3H 3H CH3 CH2 t O q C O CH CH3 NO2 d q C5H8O CHO, d J=8.1 Hz dt, J=15.8, 6.9 CHO CH ddt, J=15.8, 8.1, 1.5 t, J=7.4 CH CH2 CH3 CH2 Trans J 2Jgem = 1.5 C4H6O2 CH3 C s CH= dd 14.0, 6.6 O O C C H H H dd 14.0, 1.5 Jtrans = 14.0 Jcis = 6.6 dd 6.6, 1.5 80 MHz 400 MHz 3 3, d(2.4) 5 5, dd 9.2, 2.4 6 6, d (9.2) 3’ 3’, ddd 5.0, 1.5, 0.9 6’ 6’, dt 7.9, 1.0 5’ 5’, ddd 7.9, 7.4, 1.6 4’ 4’, ddd 7.4, 5.0 , 1.0 Protons on Heteroatoms OH, NH Exchangeable (with D2O) Hydrogen bonding On Nitrogen (14N), as the spin state of that nuclei is 1, there can be partial coupling that produce broaden lines. There can be also full coupling that would produce 3 lines of equal intensity (I=1 has 3 orientations in a magnetic field) Protons on Heteroatoms OH Aliphatic d 0.5-4.0 ppm (depend on Concentration) Intramolecular hydrogen bonding deshield OH and render it less sensitive to concentration Usually OH exchange rapidly (no coupling with neighbors In DMSO or Acetone, the exchange rate is slower = there is coupling with neighbors Phenols : d 7.5-4.0 ppm Intramolecular bond ? 12-10 ppm Carboxylic Acids: Exist as Dimers ? 13.2-10 ppm H2O signal moves with temperature H2O OH in DMSO CH3-CH2-OH OH CH2 qd (CH3)2 -CH-OH OH CH Protons on Heteroatoms NH : 14N: I=1 = 2I+1 lines NH has different rate of exchange 14N can relax quickly. Depending on relaxation rate, heteronuclear coupling will be visible or produce broadened peaks. R-NH : Aliphatic amines = rapid exchange Sharp singlets : no coupling to N: d~3-0.5 ppm R-NH: Amides, Pyrroles, Indoles, Carbamates NH broad CHa shows coupling the NH NH Amide Coupling of protons to other important nuclei 13C I = 1/2 19F = 1/2 2D = 1 Proton with Carbon-13