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- W1605489729 abstract "The reactivity of the explosive tetryl (N-methyl-N,2,4,6-tetranitroaniline; Mw = 287 u) was studied using electrospray ionization in negative mode. The main species detected in the spectrum corresponds to the ion observed at m/z 318 (previously assumed to be the odd-electron ion [tetryl + HNO]-•, C7H6O9N6). In this study, we show using D-labeling combined with high-resolution mass spectrometry that this species corresponds to an even-electron anion (i.e. C8H8O9N5), resulting from the formation of a Meisenheimer complex between tetryl and the methanol used as the solvent. Fragmentation of this complex under CID conditions revealed an unexpected fragment: the formation of a 2,4,6-trinitrophenoxide anion at m/z 228. 18O-labeling combined with quantum chemical calculations helped us better understand the reaction pathways and mechanisms involved in the formation of this product ion. This occurs via a transition state leading to a SN2-type reaction, consequently evolving toward an ion-dipole complex. The latter finally dissociates into deprotonated picric acid. Copyright © 2013 John Wiley & Sons, Ltd." @default.
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- W1605489729 date "2013-02-27" @default.
- W1605489729 modified "2023-10-16" @default.
- W1605489729 title "ESI formation of a Meisenheimer complex from tetryl and its unusual dissociation" @default.
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- W1605489729 doi "https://doi.org/10.1002/jms.3156" @default.
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