A proton magnetic resonance study of the self-condensation of formaldehyde

1976 ◽  
Vol 8 (2) ◽  
pp. 58-61 ◽  
Author(s):  
R. G. Jones ◽  
Y. Kodama
Keyword(s):  
Magnetic Resonance ◽  
Proton Magnetic Resonance ◽  
The Self ◽  
Magnetic Resonance Study ◽  
Proton Magnetic Resonance Study

A PROTON MAGNETIC RESONANCE STUDY OF N-BIS(2-HALOETHYL)AMINES

1965 ◽  
Vol 43 (6) ◽  
pp. 1792-1797 ◽  
Author(s):  
George R. Pettit ◽  
Joseph A. Settepani ◽  
Ralph A. Hill
Keyword(s):  
Magnetic Resonance ◽  
Proton Magnetic Resonance ◽  
Nitrogen Mustard ◽  
Chemical Shifts ◽  
Deuterium Oxide ◽  
The Self ◽  
Magnetic Resonance Study ◽  
Complex Series ◽  
Condensation Reactions ◽  
Proton Magnetic Resonance Study

The proton magnetic resonance chemical shifts of N-bis(2-haloethyl)amine hydrohalide salts have been found useful for rapidly assessing organohalide composition. An important illustration of nitogen mustard reactivity was obtained by observing the p.m.r. response of N-bis(2-haloethyl)amine hydrohalide salts (in deuterium oxide) following neutralization. In general, the amines rapidly entered a complex series of intra- and inter-molecular reactions. Among the substances studied N-bis(2-fluoroethyl)amine was by far the most stable and remained essentially unchanged during a 7-day period. By contrast N-bis(2-iodoethyl)amine was completely transformed in less than 6 min. The self-condensation reactions of, for example, N-bis(2-chloroethyl)amine appear to be accompanied by transient formation of N-2-chloroethylaziridine (IIIb). The present investigation indicates that p.m.r. spectroscopy is a valuable technique for evaluating the course of nitrogen mustard self-condensation reactions.

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