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Using Tandem Mass Spectrometry to Predict Chemical Transformations of 2-Pyrimidinyloxy-N-Arylbenzyl Amine Derivatives in Solution
- Source :
-
Journal of the American Society for Mass Spectrometry . Feb2006, Vol. 17 Issue 2, p253-263. 11p. - Publication Year :
- 2006
-
Abstract
- Tandem mass spectrometry is used to predict the chemical transformations of 2-pyrimidinyloxy-N-arylbenzyl amine derivatives. Compound 1 , N-2-2-4,6- dimethoxypyrimidin-2-yloxy benzylamino phenyl benzamide was selected as a model to present our idea. The CID reactions of protonated 1 include an intramolecular S N 2 reaction and a cyclodehydration reaction. Under in-source CID conditions, deprotonated 1 undergoes a Smiles rearrangement reaction and then dissociates to the ion at m/z 349. Theoretical computations were invoked to shed light on the reaction mechanisms of 1 by the semiempirical PM3 method. These studies of gas-phase reactions show the reactivity of some potential reaction centers in this molecule, which inspired us to explore the solution phase analogous reactions of 1 . Further experiments show that 1 has two analogous reactions in acidic solution: the acid-catalyzed cyclodehydration reaction and the acid-catalyzed Smiles rearrangement reaction. Moreover, 1 undergoes the base-catalyzed Smiles rearrangement under basic conditions. The present study demonstrates that mass spectrometry can play an important role in predicting the chemical solution phase transformations of 2-pyrimidinyloxy-N-arylbenzyl amine derivatives. [Copyright &y& Elsevier]
- Subjects :
- *MASS spectrometry
*CHEMICAL processes
*AMINES
*BENZAMIDE
*IONS
Subjects
Details
- Language :
- English
- ISSN :
- 10440305
- Volume :
- 17
- Issue :
- 2
- Database :
- Academic Search Index
- Journal :
- Journal of the American Society for Mass Spectrometry
- Publication Type :
- Academic Journal
- Accession number :
- 19590858
- Full Text :
- https://doi.org/10.1016/j.jasms.2005.11.001