Nielsen Michael Martin, Pedersen Christian Marcus
Department of Chemistry, University of Copenhagen Universitetsparken 5 2100 Copenhagen O Denmark
Chem Sci. 2022 May 4;13(21):6181-6196. doi: 10.1039/d2sc01125e. eCollection 2022 Jun 1.
One of the most intriguing aspects of synthetic chemistry is the interplay of numerous dependent and independent variables to achieve a successful, high-yielding chemical transformation. The experienced synthetic chemist will probe many of these variables during reaction development and optimization, which will routinely involve investigation of reaction temperature, solvent, stoichiometry, concentration, time, choice of catalyst, addition sequence or quenching conditions just to name some commonly addressed variables. Remarkably, little attention is typically given to the choice of reaction vessel material as the surface of common laboratory borosilicate glassware is, incorrectly, assumed to be chemically inert. When reviewing the scientific literature, careful consideration of the vessel material is typically only given during the use of well-known glass-etching reagents such as HF, which is typically only handled in HF-resistant, polyfluorinated polymer vessels. However, there are examples of chemical transformations that do not involve such reagents but are still clearly influenced by the choice of reaction vessel material. In the following review, we wish to condense the most significant examples of vessel effects during chemical transformations as well as observations of container-dependent stability of certain molecules. While the primary focus is on synthetic organic chemistry, relevant examples from inorganic chemistry, polymerization reactions, atmospheric chemistry and prebiotic chemistry are also covered.
合成化学最引人入胜的一个方面是众多相关和独立变量之间的相互作用，以实现成功的、高产率的化学转化。经验丰富的合成化学家在反应开发和优化过程中会探究其中许多变量，这通常包括研究反应温度、溶剂、化学计量比、浓度、时间、催化剂的选择、添加顺序或淬灭条件，这里仅列举一些常见的变量。值得注意的是，通常很少关注反应容器材料的选择，因为普通实验室硼硅酸盐玻璃器皿的表面被错误地认为是化学惰性的。在查阅科学文献时，通常只有在使用众所周知的玻璃蚀刻试剂（如HF）时才会仔细考虑容器材料，而HF通常只在耐HF的多氟聚合物容器中处理。然而，有一些化学转化的例子并不涉及此类试剂，但仍然明显受到反应容器材料选择的影响。在以下综述中，我们希望总结化学转化过程中容器效应的最重要例子以及某些分子的容器依赖性稳定性观察结果。虽然主要关注合成有机化学，但也涵盖了无机化学、聚合反应、大气化学和前生物化学的相关例子。
