TY - JOUR
T1 - Selectivity of gas-phase ion/molecule reaction of carbon dioxide with phenide ions
AU - Liu, Chongming
AU - Zhang, Yong
AU - Attygalle, Athula B.
PY - 2014/8
Y1 - 2014/8
N2 - On contrary to the widely accepted conviction that the m/z 93 ion derived from phenol does not react with CO2, we demonstrate that it makes an adduct with CO2 to a small but demonstrable extent. For example, the product-ion mass spectrum recorded for the m/z 98 ion derived from [ 2H6]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.
AB - On contrary to the widely accepted conviction that the m/z 93 ion derived from phenol does not react with CO2, we demonstrate that it makes an adduct with CO2 to a small but demonstrable extent. For example, the product-ion mass spectrum recorded for the m/z 98 ion derived from [ 2H6]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.
KW - ion/molecule reaction
KW - phenide anions
KW - phenoxide anions
KW - salicylate
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U2 - 10.1002/jms.3402
DO - 10.1002/jms.3402
M3 - Article
AN - SCOPUS:84904421056
SN - 1076-5174
VL - 49
SP - 692
EP - 699
JO - Journal of Mass Spectrometry
JF - Journal of Mass Spectrometry
IS - 8
ER -