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Fragmentation of protonated 2-(2-phenylethyl)chromones from agarwood: the diagnostic role of ion/neutral complexes as reactive intermediates

文献类型： 外文期刊

作者： Yang, Delan 1 ; Xia, Bing 2 ; Jiang, Yan 2 ; Mei, Wenli 1 ; Kuck, Dietmar 3 ;

作者机构： 1.Chinese Acad Trop Agr Sci, Inst Trop Biosci & Biotechnol, Key Lab Biol & Genet Resources Trop Crops, Minist Agr, Haikou 571101, Peoples R China

2.Chinese Acad Sci, Chengdu Inst Biol, Chengdu 610041, Peoples R China

3.Univ Bielefeld, Dept Chem, D-33615 Bielefeld, Germany

关键词： chromones;2-(2-phenylethyl)-;agarwood;ion/neutral complexes;chromylium ions;ESI mass spectrometry;tandem mass spectrometry;substituent effects;Grob fragmentation

期刊名称：EUROPEAN JOURNAL OF MASS SPECTROMETRY （ 影响因子：1.067； 五年影响因子：0.981 ）

ISSN：

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收录情况： SCI

摘要： A positive-ion electrospray ionisation collision-induced dissociation mass spectrometric study on the fragmentation of the [M + H](+) ions of 2-(2-phenylethyl)chromone and a set of nine hydroxyl- and/or methoxy-substituted derivatives has revealed a highly prominent fragmentation channel, the loss of benzoquinomethanes or a benzaldehyde, respectively, as a diagnostic feature for 2-(2-phenylethyl)chromones that bear a hydroxyl group at the para- (4'-), ortho-(2'-) and/or benzylic (alpha-) position of the phenylethyl residue. Derivatives that bear only a meta-(3'-) hydroxyl group do not undergo this elimination. The intermediacy of ion/neutral complexes (INCs) is invoked to explain this fragmentation, which involves the remarkable intra-complex proton or hydrogen atom transfer from the remote 4'-OH (or the 2'- or alpha-OH) functionalities. Density functional theory (B3LYP/6-31G(d)) calculations confirm the energetic preference for these elimination channels and agree with the limited thermochemical data known for para- and ortho-benzoquinomethanes. The INC-mediated losses of the benzaldehydes from the [M + H](+) ions of the alpha-hydroxy-substituted 2-(2-phenylethyl) chromones correspond to a particularly facile (vinylogous) Grob fragmentation. The study may be viewed as a telling example of the diagnostic role of ion/neutral complexes as intermediates for the structural assignment of constitutional isomers by mass spectrometry.

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