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The properties and applications of 2-methyl-(2 H )-tetrazole-5-amino-saccharinate ( 2MTS ) in catalysis and chelant-based chemotherapy stimulated investigations on its photostability. The photochemistry of monomeric  2MTS  in solid argon (15 K) was compared with those of 2-methyl-(2 H )-tetrazole-5-amine ( 2MT ) and 1-methyl-(2 H )-tetrazole-5-amine ( 1MT ). Compounds were subjected to  in situ  narrowband UV-irradiation at different wavelengths. Reactions were followed by infrared spectroscopy, supported by B3LYP/6-311++G(d,p) calculations. Photochemical pathways for  2MT  and  2MTS  proved similar but photodegradation of  2MTS  was 20× slower, unraveling the photostabilizing effect of the saccharyl moiety that extends into the nitrilimine formed from  2MTS  and its antiaromatic 1 H -diazirene isomer, which proved photostable at 290 nm, unlike the 1 H -diazirene formed from  2MT . Analysis of the photochemistries of  2MTS / 2MT  (250 nm) and  1MT  (222 nm), including energy trends calculated for the isomeric C 2 H 5 N 3  species postulated/observed from photolysis and EPR results, enabled a deeper insight into the photodegradation mechanisms of 1,5-substituted and 2,5-substituted tetrazoles. We postulate a pivotal singlet state imidoylnitrene species,   s N1 , as common intermediate, which undergoes a Wolff-type isomerization to a stable carbodiimide. Photo-extrusion of N 2  from 1,5-substituted tetrazoles generates   s N1  directly but from 2,5-substituted tetrazoles it originates a nitrilimine, then a diazirene, which finally leads to   s N1 . Selective formation of cyanamide from  1MT  requires photoisomerization between   s N1  and   s N2 , accessible at 222 nm. EPR studies enabled the detection of methyl nitrene, arising from photolysis of 1 H -diazirene intermediate.

pure and applied chemistry

Insights into the photochemistry of 5-aminotetrazole derivatives with applications in coordination chemistry. Effect of the saccharyl moiety on the photostability