Neighboring group participation in the electrospray ionization tandem mass spectra of polyamine toxins of spiders. Part 1: α, ω-diaminoalkane compounds.

The fragmentation pattern of N-(4-aminobutyl)-3-(4-hydroxyphenyl)prop-2-enamide (1) is characterized by an ion formed by neighboring group participation. The phenolic hydrogen is transferred to the primary amino group via a 15-membered ring. This has been proven by H/D exchange reactions and by analyzing homologues and derivatives.