Mass spectra of heterocyclic compounds. II‐Hexahydro‐1,3,5,‐triazines

Abstract

The twelve tri-N-sulphonylhexahydro-l,3,5-triazines (R = alkyl or aryl) exhibit a common fragmentation pattern; most of the fragments are directly or indirectly generated from the [M -RSOJ+ ion. Tri-N-BenzylsulphonyIhexahydro-1,3,5-triazine (R = PhCH2) departs from the others mainly because the key ion [M -RSOa]+ suffers a skeletal rearrangement with loss of SO,. The rationalizations presented are supported by metastable evidence, accurate mass measurements and deuterium labelling.

The ESI CAD fragmentations of protonated 2,4,6‐tris(benzylamino)‐ and tris(benzyloxy)‐1,3,5‐triazines involve benzyl–benzyl interactions: a DFT study

“…As a part of an ongoing synthetic research program toward the synthesis of s ‐triazine derivatives for structural investigation and evaluation of their biological activity, we have synthesized a new series of 2,4,6‐tri substituted s ‐triazines . The applications of electron ionization and electrospray ionization (ESI) mass spectrometry to various substituted triazines are well known in the literature . Tandem mass spectrometric experiments have shown that the dissociation of protonated molecules containing more than one benzyl groups yield product ion of m/z 181 having molecular formula C 14 H 13 + due to benzyl‐benzyl interactions .…”

“…[16] The applications of electron ionization and electrospray ionization (ESI) mass spectrometry to various substituted triazines are well known in the literature. [17][18][19][20][21][22][23][24][25][26][27][28][29][30][31][32][33][34][35][36] Tandem mass spectrometric experiments have shown that the dissociation of protonated molecules containing more than one benzyl groups yield product ion of m/z 181 having molecular formula C 14 H 13 + due to benzyl-benzyl interactions. [37][38][39][40][41][42] Examples include study of the protonated dibenzyl esters of dicarboxylic acid generated by chemical ionization [40] and N,N 0 -dibenzylpiperzines produced by ESI.…”