Document Detail

Mass spectral fragmentation pathways of propranolol related beta-fluorinated amines studied by electrospray and electron impact ionization.
MedLine Citation:
PMID:  10440986     Owner:  NLM     Status:  MEDLINE    
Propranolol, its 1"-mono-, di-, and trifluorinated analogs, and other related compounds were analyzed under electrospray ionization ion trap collision-induced dissociation (ESI-CID) and electron impact (EI) conditions. Interesting trends were observed in the fragment ions formed in both cases. Under ESI conditions, the abundances of product ions easily explained by protonation on the amine nitrogen decreased relative to the abundances of those formed from the ether-protonated species as the number of fluorines increased from zero to three. Under EI conditions, the distribution of fragment ions was shifted away from those arising from a nitrogen-centered cation radical and toward those arising from an ether oxygen-centered cation radical. The changes observed in apparent molecular sites of protonation and of ion radical formation in the mass spectra are consistent with the electron-withdrawing effects of the sequentially added fluorines. These effects are correlated with changes in solution phase pK( a)'s of the fluorinated amines.
A L Upthagrove; M Hackett; W L Nelson
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Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't; Research Support, U.S. Gov't, P.H.S.    
Journal Detail:
Title:  Rapid communications in mass spectrometry : RCM     Volume:  13     ISSN:  0951-4198     ISO Abbreviation:  Rapid Commun. Mass Spectrom.     Publication Date:  1999  
Date Detail:
Created Date:  1999-09-28     Completed Date:  1999-09-28     Revised Date:  2007-11-14    
Medline Journal Info:
Nlm Unique ID:  8802365     Medline TA:  Rapid Commun Mass Spectrom     Country:  ENGLAND    
Other Details:
Languages:  eng     Pagination:  1671-9     Citation Subset:  IM    
Copyright Information:
Copyright 1999 John Wiley & Sons, Ltd.
Department of Medicinal Chemistry, University of Washington, Seattle, WA 98195-7610, USA.
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MeSH Terms
Adrenergic beta-Antagonists / chemistry*
Fluorine Compounds
Mass Spectrometry / methods
Propranolol / analogs & derivatives*,  chemistry*
Grant Support
Reg. No./Substance:
0/Adrenergic beta-Antagonists; 0/Fluorine Compounds; 525-66-6/Propranolol

From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine

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