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Structural isomer differentiation of 1,6‐diaza‐3,8‐dioxabicyclo[4.4.1]undecane and N,N ′‐methylenebis(oxazolidine) by mass spectrometry
Author(s) -
Monnier Valérie,
Libot Francine,
Aitken David J.,
Husson HenriPhilippe,
Lesage Denis,
Fournier Françoise,
Tabet JeanClaude
Publication year - 2002
Publication title -
rapid communications in mass spectrometry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.528
H-Index - 136
eISSN - 1097-0231
pISSN - 0951-4198
DOI - 10.1002/rcm.585
Subject(s) - chemistry , undecane , oxazolidine , mass spectrometry , computational chemistry , organic chemistry , chromatography
The title compound types are structural isomers. The absence of literature studies dealing with the mass spectrometric gas‐phase behavior of such compounds prompted a search for the best conditions for differentiation between the two prototype examples ( R,R )‐5,10‐diphenyl‐1,6‐diaza‐3,8‐dioxabi‐cyclo[4.4.1]undecane and N,N ′‐methylenebis[( R )‐4‐phenyloxazolidine]. Attempts to differentiate between the isomers by NMR were inconclusive and X‐ray crystallography had to be used. The best mass spectrometric results were obtained using gas‐phase ionization techniques, particularly chemical ionization, whereby protonated molecules were observed. The fragmentation pathways were elucidated from MS/MS studies and from experiments performed on hexadeuterated samples of each compound. Copyright © 2002 John Wiley & Sons, Ltd.