Abstract
Isoselenocyanates are known to react with primary and secondary amines to produce the corresponding selenoureas. p-Tolyl isoselenocyanate was prepared and its reaction with various primary and secondary amines was investigated. The resulting selenoureas were characterized by multinuclear ( 13C and 77Se) magnetic resonance spectroscopy. Since these selenoureas possess a CSe bond, the 77Se chemical shifts display a high sensitivity to the chemical and electronic environment of the nucleus and a large range for relatively minor changes in chemical structure. The rationale for the choice of p-tolyl isoselenocyanate is that it clearly resembles, in both structure and reactivity, the corresponding, well-studied, phenyl isothiocyanate (Edman's reagent), which has widespread applicability in the sequencing of amino acid residues in polypeptides and proteins.
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