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Chemical ionization mass spectra of acetals of β‐ D ‐glycopyranosylnitromethanes
Author(s) -
Kováčik Vladimír,
Pätoprstý Vladimír,
Petruš Ladislav,
Ovcharenko Vladimir,
Pihlaja Kalevi
Publication year - 2000
Publication title -
journal of mass spectrometry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.475
H-Index - 121
eISSN - 1096-9888
pISSN - 1076-5174
DOI - 10.1002/(sici)1096-9888(200005)35:5<634::aid-jms989>3.0.co;2-5
Subject(s) - chemistry , isobutane , pyridine , chemical ionization , mass spectrum , ion , adduct , mass spectrometry , benzene , electrophile , medicinal chemistry , ring (chemistry) , dissociation (chemistry) , ionization , analytical chemistry (journal) , stereochemistry , organic chemistry , catalysis , chromatography
O ‐Isopropylidene and O ‐benzylidene acetals of common 2,6‐anhydro‐1‐deoxy‐1‐nitroalditols (β‐ D ‐glycopyranosylnitromethanes) derived from D ‐glucose, D ‐galactose and D ‐mannose were studied by chemical ionization mass spectrometry (CIMS) using methane, isobutane, ammonia or pyridine as reaction gas. Production of [M+H] + adduct ions dominates in the case of methane or isobutane possessing proton affinity values PA = 552 or 683 kJ mol −1 , respectively. The collision‐induced dissociation time‐of‐flight product ion spectra of [M+H] + ions differ characteristically according the stereochemical arrangement of the pyranoid ring. These differences can be helpful when assigning stereochemical arrangements for the pyranoid ring. The dominant process in ammonia ( PA = 853 kJ mol −1 ) CIMS for most of the compounds studied is the production of the cluster ions [M+NH 4 ] + . The cluster [M+pyridineH] + ions are observable only for substances possessing the O ‐benzylidene group ( PA of pyridine = 924 kJ mol −1 ). Copyright © 2000 John Wiley & Sons, Ltd.