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    
Abstract/OtherAbstract:
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.
Authors:
A L Upthagrove; M Hackett; W L Nelson
Related Documents :
11747116 - Structure characterization of flavonoid o-diglycosides by positive and negative nano-el...
16750386 - Characterization of cardiolipin as the sodiated ions by positive-ion electrospray ioniz...
19206216 - Thermal behavior of j-aggregates in a langmuir-blodgett film of pure merocyanine dye in...
14753866 - Evidence for nonhadronic degrees of freedom in the transverse mass spectra of kaons fro...
426 - Murexide for determination of free and protein-bound calcium in model systems.
10194376 - Electron and proton transfer on the acceptor side of the reaction center in chromatopho...
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.
Affiliation:
Department of Medicinal Chemistry, University of Washington, Seattle, WA 98195-7610, USA.
Export Citation:
APA/MLA Format     Download EndNote     Download BibTex
MeSH Terms
Descriptor/Qualifier:
Adrenergic beta-Antagonists / chemistry*
Animals
Fluorine Compounds
Humans
Mass Spectrometry / methods
Propranolol / analogs & derivatives*,  chemistry*
Grant Support
ID/Acronym/Agency:
GM-07750/GM/NIGMS NIH HHS; RR-13400/RR/NCRR NIH HHS
Chemical
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


Previous Document:  Energy-resolved mass spectrometry: a comparison of quadrupole cell and cone-voltage collision-induce...
Next Document:  Effect of nitro groups and alkyl chain length on the negative ion tandem mass spectra of alkyl 3-hyd...