A gas‐phase investigation of the D‐fructose dehydration reaction in the presence of base has been performed by the joint application of mass spectrometric techniques and theoretical calculations. Protonated addition products of D‐fructose and base were generated in the gas phase by electrospray ionization using several bases of different proton affinity. The intermediates, products and decomposition channels were investigated by ion trap mass spectrometry. Electronic structure calculations allowed the identification of the ionic intermediates and products of a selected system containing NH₃, helping to rationalize the observed reaction pathways. The obtained results show that the final product, the protonated 5‐hydroxymethyl‐2‐furaldheyde [5‐HMF]H⁺, is better formed using selected bases and only if these remain clustered until the end of the dehydration process.

中文翻译：

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基地辅助的将质子化的果糖转化为5-HMF：寻找气相绿色模型。

质谱技术和理论计算的联合应用已在碱存在下对D-果糖脱水反应进行了气相研究。使用几种质子亲和力不同的碱通过电喷雾电离在气相中生成了D-果糖和碱的质子化加成产物。通过离子阱质谱法研究了中间体，产物和分解通道。电子结构计算可以鉴定选定的含NH _3的系统的离子中间体和产物，从而有助于合理化所观察到的反应路径。所得结果表明，最终产物质子化的5-羟甲基-2-糠醛[5-HMF] H⁺可以使用选定的碱更好地形成，并且前提是这些碱必须保持聚簇直至脱水过程结束。