首页> 外文期刊>Journal of mass spectrometry: JMS >Gas-phase ion-molecule reaction of alpha-phenylvinyl cation towards substituted benzenes in the environment of an ITMS
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Gas-phase ion-molecule reaction of alpha-phenylvinyl cation towards substituted benzenes in the environment of an ITMS

机译:ITMS环境中α-苯基乙烯基阳离子对取代苯的气相离子分子反应

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摘要

Ion-molecule reactions between the α-phenylvinyl cation (α-PVC) and mono-substituted benzenes have been investigated using a quadrople ion-trap mass spectrometer. The α-PVC, generated by chemical ionization from phenylacetilene, was found to react selectively with mono-substituted benzenes bearing electron withdrawing groups to give the product ions [M + 103] ~+ and the trans-vinylating product ions [M + 25]~+. To characterize the reaction products, a combination of collision-induced dissociation, isotope-labeling experiments and model compounds were used. The results indicate, in addition to direct heteroatom alkylation, high extent of ortho attack. We attributed the positional selectivity of the α-PVC to the nature of the substituent on the neutral molecule. In particular, hydroxy and amino groups promoted the alkenylation at ortho position.
机译:使用四重离子阱质谱仪研究了α-苯基乙烯基阳离子(α-PVC)与单取代苯之间的离子分子反应。发现由苯乙炔化学电离生成的α-PVC与带有吸电子基团的单取代苯选择性反应,生成产物离子[M + 103]〜+和反乙烯基化产物离子[M + 25] 〜+。为了表征反应产物,使用了碰撞诱导的解离,同位素标记实验和模型化合物的组合。结果表明,除了直接的杂原子烷基化以外,邻位攻击的程度也很高。我们将α-PVC的位置选择性归因于中性分子上取代基的性质。特别地,羟基和氨基促进邻位的烯基化。

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