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Effect of nitro groups and alkyl chain length on the negative ion tandem mass spectra of alkyl 3‐hydroxy‐5‐(4′‐Nitrophenoxy) and alkyl 3‐hydroxy‐5‐(2′, 4′‐dinitrophenoxy) benzoates
Author(s) -
Kangas Heli,
Franzén Robert,
Tois Jan,
Taskinen Jyrki,
Kostiainen Risto
Publication year - 1999
Publication title -
rapid communications in mass spectrometry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.528
H-Index - 136
eISSN - 1097-0231
pISSN - 0951-4198
DOI - 10.1002/(sici)1097-0231(19990830)13:16<1680::aid-rcm698>3.0.co;2-r
Subject(s) - chemistry , benzoates , alkyl , mass spectrum , substituent , ion , nitro , medicinal chemistry , fragmentation (computing) , tandem mass spectrometry , mass spectrometry , organic chemistry , chromatography , computer science , operating system
Tandem mass spectrometric behaviour was studied for a small combinatorial library of alkyl 3‐hydroxy‐5‐(4′‐nitrophenoxy) benzoates (A1–A5) and alkyl 3‐hydroxy‐5‐(2′, 4′‐dinitrophenoxy) benzoates (B1–B5). The spectra were recorded by negative ion electrospray low‐energy collision induced dissociation (CID) tandem mass spectrometry. The product ion spectra of [M − H] − of the benzoates A1–A5 are similar, as are those of benzoates B1–B5. However, the spectra of the B series compounds differ significantly from those of the A series owing to the second electron‐withdrawing nitro substituent in the B compounds. In addition, the length of the alkyl chain has an effect on the fragmentation. However, both series of compounds exhibit an abundant nitrophenoxy ion formed by the loss of 3‐hydroxybenzoate. This is at m/z 138 in A1–A5 and at m/z 183 in B1–B5. A precursor ion scan of the nitrophenoxy ion provides a rapid method to identify the synthesised compounds in this type of combinatorial mixture. Copyright © 1999 John Wiley & Sons, Ltd.