By Walker S., Muliere P.

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14), for aliphatic compounds Indication of S : Isotope peak [M+2]+' 2 5% M+' Am 33, 34, 47, 48, 64, 65 from M+' Am 34, 48, 64 from Frag+ mtz 33,34,35 mtz 45 in O-free compounds m/z 47, 61, 75, 89,... 8 Rules for Determining the Relative Molecular Weight (Mr) The molecular ion (M+') is defined as the ion that comprises the most abundant isotopes of the elements in the molecule. Interestingly, the lightest isotopes of most elements that frequently occur in organic compounds and their common salts (H, C, N, 0, F, Si, P, S, C1, As, Br, I, Na, Mg, Al, K, Ca, Rb, Cs) are also the most abundant ones.

Hz 5 n=4 = 4 . 3 ppm ~ 2 . ppm 6 ~ 2 . ~ dZ 90-92 m$ m/z 127 <- m/z 152, 153 eka Rearrangements uv 1 -200-210 nm (log E -4) -260 nm (log E ~ 2 . 4 ) m/z 152, 165 +. 5 Heteroaromatic Compounds Assignment ar c-x ar C-C Range 120-160 ppm 100-150 ppm H i C ar) 6-9 ppm HiN ar) 7-1 4 ppm ar C-H st ar N-H st ar c-c st ar C-H 6 oop Molecular ion Fragments Comments 13c N M R Coupling constants in 6-membered rings similar to those in aromatic hydrocarbons; in 5-membered heteroaromatic rings smaller Strongly solvent dependent, generally broad IR 3100-3000 cm-l Often multiple bands, weak 3500-2800 cm-l 1600 cm-l Often split, sometimes not all three -1500 cm-l ~ 1 4 5 cm-l 0 bands observable 1000-650 cm-l Often strong, frequently multiple bands - m Strong, often base peak m/z 39, 50-53, Often doubly charged fragment ions 63-65,75-78 [M-26]+', [M-39]+ benzyl-analogous cleavage Rearrangements m/z 45 [CHS]+ 1H N M R Loss of HCN (N-heteroaromatics) Loss of CO (0-heteroaromatics) Loss of CS (S-heteroaromatics) S-Heteroaromatics l + +.

3 ppm ~ 2 . ppm 6 ~ 2 . ~ dZ 90-92 m$ m/z 127 <- m/z 152, 153 eka Rearrangements uv 1 -200-210 nm (log E -4) -260 nm (log E ~ 2 . 4 ) m/z 152, 165 +. 5 Heteroaromatic Compounds Assignment ar c-x ar C-C Range 120-160 ppm 100-150 ppm H i C ar) 6-9 ppm HiN ar) 7-1 4 ppm ar C-H st ar N-H st ar c-c st ar C-H 6 oop Molecular ion Fragments Comments 13c N M R Coupling constants in 6-membered rings similar to those in aromatic hydrocarbons; in 5-membered heteroaromatic rings smaller Strongly solvent dependent, generally broad IR 3100-3000 cm-l Often multiple bands, weak 3500-2800 cm-l 1600 cm-l Often split, sometimes not all three -1500 cm-l ~ 1 4 5 cm-l 0 bands observable 1000-650 cm-l Often strong, frequently multiple bands - m Strong, often base peak m/z 39, 50-53, Often doubly charged fragment ions 63-65,75-78 [M-26]+', [M-39]+ benzyl-analogous cleavage Rearrangements m/z 45 [CHS]+ 1H N M R Loss of HCN (N-heteroaromatics) Loss of CO (0-heteroaromatics) Loss of CS (S-heteroaromatics) S-Heteroaromatics l + +.

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