Control of Conformation and Reactivity in Pentafluorosulfanyl and Tetrafluorosulfanyl Substituted Aliphatic Compounds

五氟硫基和四氟硫基取代的脂肪族化合物的构象和反应性的控制

• 批准号: 1464936
• 负责人: John Welch
• 金额: $ 39万
• 依托单位: SUNY at Albany
• 依托单位国家: 美国
• 项目类别: Standard Grant
• 财政年份: 2015
• 资助国家: 美国
• 起止时间: 2015-06-15 至 2021-09-30
• 项目状态: 已结题
• 来源: https://www.nsf.gov/awardsearch/showAward?AWD_ID=1464936&HistoricalAwards=false
• 关键词: Control; Conformation; Reactivity; Pentafluorosulfanyl; Tetrafluorosulfanyl

In this project funded by the Chemical Synthesis program of the Chemistry Division, Professor John Welch of the University at Albany is developing new fluorine containing functional groups. Fluorinated compounds are widely employed in life sciences and materials research. Nearly 20% of all pharmaceuticals and 40% of all agrochemicals contain fluorine. Fluorination and fluorinated functional groups have added value and utility to materials for 75 years yet it has been increasingly apparent that these useful substituents can be accompanied by undesirable environmental effects. Prof. Welch is training graduate students to handle extraordinarily reactive reagents to prepare novel fluorinated reactants. Prof. Welch operates and makes available to the scientific community a dedicated laboratory equipped with the necessary infrastructure for the preparation, purification and characterization of both liquid and gaseous reactive fluorinated intermediates and synthons. The relationship between structure and reactivity of aliphatic fluorinated hypervalent sulfur compounds is under investigation. Although the chemistry of the pentafluorosulfanyl group is very much in its infancy, the Welch group is exploring the use of environmentally more benign hypervalent fluorinated sulfur compounds to deliver the desired effects of fluorination while mitigating the undesirable aspects, e.g., by decomposing in an environmentally benign manner. The influence of steric demand, electronegativity and dipole moment on the physical properties, conformation, and selectivity of beta-lactams, amino acids and peptides containing fluorinated hypervalent sulfur is being explored. The role of trifluoromethyl substitution in the SF5-group (i.e. the new SF4(CF3) group) is under investigation. In comparing the SF5 and SF4(CF3) substituents, differences in selectivity and reactivity will be examined. An effort will be made to establish whether such differences correlate with trends in dipole moment or electron-withdrawing ability of these two new, heavily fluorinated substituents.

在这个由化学系化学合成计划资助的项目中，奥尔巴尼大学的约翰·韦尔奇教授正在开发新的含氟官能团。 含氟化合物在生命科学和材料研究中有着广泛的应用。 近20%的药物和40%的农用化学品含有氟。75年来，氟化和氟化官能团为材料增加了价值和实用性，但越来越明显的是，这些有用的取代基可能伴随着不期望的环境影响。 韦尔奇教授正在培训研究生处理反应性极强的试剂，以制备新型氟化反应物。Welch教授经营并向科学界提供了一个专用实验室，该实验室配备了必要的基础设施，用于制备，纯化和表征液体和气体反应性氟化中间体和半导体。 研究了脂肪族含氟高价硫化合物的结构与反应活性之间的关系。 尽管五氟硫烷基的化学研究还处于起步阶段，但韦尔奇小组正在探索使用对环境更有利的高价氟化硫化合物来提供所需的氟化效果，同时减轻不期望的方面，例如，通过对环境无害的方式分解。 正在探索空间需求、电负性和偶极矩对含氟化高价硫的β-内酰胺、氨基酸和肽的物理性质、构象和选择性的影响。三氟甲基取代在SF 5-基团（即新的SF 4（CF 3）基团）中的作用正在研究中。在比较SF 5和SF 4（CF 3）取代基时，将检查选择性和反应性的差异。将作出努力，以确定是否与这两个新的，重氟化取代基的偶极矩或吸电子能力的趋势，这种差异。

项目成果

Photosensitive Hypervalent Fluorinated Sulfur Containing Polymers for Light Sensitive Applications

用于光敏感应用的光敏高价氟化含硫聚合物

• DOI: 10.1002/pol.20190104
• 发表时间: 2020
• 期刊: Journal of Polymer Science
• 影响因子: 3.4
• 作者: Bonetti, Kelly A.;Murphy, Michael;Brainard, Robert L.;Zhong, Linbin;Welch, John T.
• 通讯作者: Welch, John T.