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Eur. J. Mass Spectrom. 1, 539 - 543 (1995)

Acetone chemical ionization studies. VIII: pyridine derivatives

M. Vairamani,* S. Prabhakar, N. Prasada Raju and G.K. Viswanadha Rao
Indian Institute of Chemical Technology, Hyderabad 500 007, India.

ABSTRACT:
Acetone chemical ionization mass spectra of pyridine and 23 isomeric alkyl, dialkyl, amino, hydroxy, cyano and halo pyridines were studied. The formation of [M + H]+ ions and the adducts corresponding to [M + 43]+and [M + 59]+ ions is controlled by the proton affinity of the substrate and the position of the substituent. The acetylation reaction is less pronounced in 2-substituted pyridines due to steric factors, except in amino and hydroxypyridines where the acetylated ion is stabilized through hydrogen bonding. Collision-induced dissociation (CID) spectra of [M + 43]+ ions of isomeric amino and hydroxypyridines suggest acetylation occurs mainly at the ring nitrogen.

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