The preparation and characterization of some fluorinated α-aminoarylmethanephosphonic acids

Article abstract of DOI:10.1080/10426509608046389

α-Aminoarylmethanephosphonic acids have been prepared with a range of fluoro, fluoroalkyl, or fluoroalkoxy substituents in the benzene ring (4-F, 3-F, 2-F, 3,4-F₂, F₅, 4-CF₃, 3-CF₃, 4-CF₃O, and 3-CF₃O). These compounds have relatively low aqueous solubility and their NMR spectra (¹H, ¹³C, ³¹P and ¹⁹F) were therefore recorded in D₂O in the presence of an excess of alkali. Under these conditions, the ring substituents appear to have little effect on δp (15-18 ppm), or on the ¹H and ¹³C parameters for the benzylic group (α-CH), which are mainly in the ranges observed for other types of α-aminoarylmethanephosphonic acids under alkaline conditions (δ_H 3.8-4.0 ppm, ²J_PH 15.3-16.5 Hz; δ_C 57-58 ppm, ¹J_PC 128-132 Hz). For those examples with fluorine in the ortho position (i.e., the 2-fluoro and pentafluoro derivatives) a slightly higher field chemical shift was observed for the benzylic carbon atom (δ_C 50-51 ppm). In the fast-atom bombardment mass spectra, pseudo-molecular ions, MH⁺, and ions resulting from the elimination of phosphorous acid [MH - H₃PO₃]⁺, provide a further useful means of chararacterization for these compounds. Key words: Fluorinated aminoarylmethanephosphonic acids, dialkyl N-diphenylmethylaminoaryl-methanephosphonates, NMR spectroscopy, FAB mass spectrometry.

Full text of DOI:10.1080/10426509608046389

This article was downloaded by: [Universite Laval]
On: 06 October 2014, At: 23:28
Publisher: Taylor & Francis
Informa Ltd Registered in England and Wales Registered Number: 1072954 Registered
office: Mortimer House, 37-41 Mortimer Street, London W1T 3JH, UK
Phosphorus, Sulfur, and Silicon and the
Related Elements
Publication details, including instructions for authors and
subscription information:
http://www.tandfonline.com/loi/gpss20
THE PREPARATION AND
CHARACTERIZATION OF
SOME FLUORINATED α-
AMINOARYLMETHANEPHOSPHONIC ACIDS
Donovan St. C. Green a , Ulrike Gruss b , Gerhard Hägele b , Harry R.
Hudson a , Lars Lindblom a & Max Pianka a
a School of Applied Chemistry, University of North London , 166-220
Holloway Road, London, N7 8DB, United Kingdom
b Institut für Anorganische Chemie und Strukturchemie I, Heinrich
Heine-Universität Düsseldorf , Universitätsstraβe 1, D-40225,
Düsseldorf, Germany
Published online: 04 Oct 2006.
To cite this article: Donovan St. C. Green , Ulrike Gruss , Gerhard Hägele , Harry R. Hudson , Lars
Lindblom & Max Pianka (1996) THE PREPARATION AND CHARACTERIZATION OF SOME FLUORINATED α-
AMINOARYLMETHANEPHOSPHONIC ACIDS, Phosphorus, Sulfur, and Silicon and the Related Elements,
113:1-4, 179-207, DOI: 10.1080/10426509608046389
To link to this article: http://dx.doi.org/10.1080/10426509608046389
PLEASE SCROLL DOWN FOR ARTICLE
Taylor & Francis makes every effort to ensure the accuracy of all the information (the
“Content”) contained in the publications on our platform. However, Taylor & Francis,
our agents, and our licensors make no representations or warranties whatsoever as to
the accuracy, completeness, or suitability for any purpose of the Content. Any opinions
and views expressed in this publication are the opinions and views of the authors,
and are not the views of or endorsed by Taylor & Francis. The accuracy of the Content
should not be relied upon and should be independently verified with primary sources
of information. Taylor and Francis shall not be liable for any losses, actions, claims,
proceedings, demands, costs, expenses, damages, and other liabilities whatsoever or
howsoever caused arising directly or indirectly in connection with, in relation to or arising
out of the use of the Content.
This article may be used for research, teaching, and private study purposes. Any
substantial or systematic reproduction, redistribution, reselling, loan, sub-licensing,
systematic supply, or distribution in any form to anyone is expressly forbidden. Terms &

Conditions of access and use can be found at http://www.tandfonline.com/page/terms-
and-conditions