Abstract
Dimethyl dihydro-1,2,4,5-tetrazine-3,6-dicarboxylate can exist either in 1,2- or 1,4-dihydro tautomeric forms. The 15N NMR spectra of dimethyl dihydro-1,2,4,5-tetrazine-3,6-dicarboxylate were measured at the 15N natural abundance level as well as in 15N doubly labelled selectively and in 15N completely labelled compounds (20% 15N). The J( 15N, 15N) value was determined in 15N completely labelled compounds (20% 15N) using 1D 15N INADEQUATE and was found to be 12.2 ± 0.2 Hz in deuteriochloroform, acetonitrile- d 3, DMSO- d 6 and CD 3OH. Very similar 15N chemical shifts and 1 J( 15N, 1H) values were also observed in all the solvents. This indicates that compound 1 exists completely in the 1,4-dihydro tautomeric form (i.e., as dimethyl 1,4-dihydro-1,2,4,5-tetrazine-3,6-dicarboxylate) in all the solvents tested.
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