RUI: Electrophilic Reactions of Fluorosubstituted Alkenes- Predicting Regiochemical Product Distributions

该奖项授予加州圣地亚哥洛马拿撒勒学院化学系的Dale F. Shellhamer教授，其目标是了解乙烯基氟原子对与卤素、卤素间素和开放离子亲电试剂（如三羧酸和氯磺酰异氰酸酯）发生的亲电反应的产物区域化学的影响。这一点很重要，因为我们知道氟比其他任何元素都更有能力完全改变亲电反应的产物区域化学。除实验研究外，量子化学计算研究将用于预测和验证氟原子对产品分布的预期剧烈变化。此外，拟议的氯磺酰异氰酸酯研究将提供一类新的氟β -内酰胺，这是一项重要的研究，因为β -内酰胺的功能存在于几类抗生素中。此外，对含氟化合物的研究很重要，因为大量农用化学品和药品都含有氟原子。这项研究最重要的广泛影响之一是指导本科生研究人员，并在一个以本科生为主的机构中将他们培养成未来的科学家。Shellhamer教授和Point Loma Nazarene学院在这方面堪称典范，他们的本科生研究参与者获得科学和医学高级学位的记录非常出色。它们在少数民族和女性学生的参与方面也有良好的记录，预计这种情况将继续下去。此外，如上所述，由于许多药品和农用化学品中都含有氟，因此了解氟的化学性质将有助于设计新一代这些物质。

This award to Professor Dale F. Shellhamer of the Chemistry Department at Point Loma Nazarene College in San Diego, CA has as its goal the understanding of the influence that vinyl fluorine atoms have on the product regiochemistry from electrophilic reactions with halogens, interhalogens, and open-ion electrophiles like triflic acid and chlorosulfonyl isocyanate. This is important since it is known that fluorine, more than any other element, has the ability to completely alter product regiochemistry for electrophilic reactions. In addition to the experimental studies, quantum chemical computational studies will be employed to predict and verify the anticipated drastic changes that fluorine atoms have on product distributions. Further, the proposed study with chlorosulfonyl isocyanate will provide a new class of fluoro beta-lactams, an important study since beta-lactam functionality is present in several classes of antibiotics. Further, studies of fluorine containing compounds are important since a large number of agrochemicals and pharmaceuticals contain fluorine atoms.Among the most important broader impacts of this research is the mentoring of undergraduate researchers and training them as future scientists in a predominantly undergraduate institution. Prof. Shellhamer and Point Loma Nazarene College are exemplary in this regard and they have an excellent record of their undergraduate research participants obtaining advanced degrees in science and medicine. They also have an excellent record of participation by minority and women students and it is expected that this will continue. Further, as mentioned above, because fluorine is found in many pharmaceuticals and agrochemicals, understanding the chemistry of fluorine will help in the design of new generations of these substances.