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Selectivity of gas‐phase ion/molecule reaction of carbon dioxide with phenide ions
Author(s) -
Liu Chongming,
Zhang Yong,
Attygalle Athula B.
Publication year - 2014
Publication title -
journal of mass spectrometry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.475
H-Index - 121
eISSN - 1096-9888
pISSN - 1076-5174
DOI - 10.1002/jms.3402
Subject(s) - chemistry , adduct , ion , decarboxylation , phenol , molecule , mass spectrometry , qualitative inorganic analysis , polyatomic ion , medicinal chemistry , photochemistry , inorganic chemistry , organic chemistry , catalysis , chromatography
On contrary to the widely accepted conviction that the m/z 93 ion derived from phenol does not react with CO 2 , we demonstrate that it makes an adduct with CO 2 to a small but demonstrable extent. For example, the product‐ion mass spectrum recorded for the m/z 98 ion derived from [ 2 H 6 ]phenol showed a small peak at m/z 142 when CO 2 was used as the collision gas. The formation of an m/z 137 adduct ion from the m/z 93 ion (generated either directly from phenol, or indirectly from salicylic acid by in‐source decarboxylation) was demonstrated also by multiple‐reaction‐monitoring tandem mass spectrometric experiments. According to literature, the m/z 93 ion derived from salicylic acid does not undergo CO 2 addition because it is deemed to exist only in the phenoxide form. This reaction has been previously proposed as a method for differentiating phenoxide ion from its isomeric hydroxyphenide ions. We propose that the m/z 93 ion, albeit small, exists also as the phenide form together with the predominant phenoxide ion. Copyright © 2014 John Wiley & Sons, Ltd.