Atmospheric Chemistry Program Seminar
The Synthesis and Reactions of 3-Hydroxymethylphthalimides by Olivia Jenks, CU ANYL Chem 1st Year, de Gouw group
"Phthalimides possess a wide range of physiological properties, including anti-inflammatory and immunomodulatory activities, and have been found to be useful in the preparation of specialized polymers and macrocycles. While a vast number of N-substituted phthalimides have been reported, the number of phenyl-substituted compounds is fairly limited. We have recently developed a convenient method for the synthesis of 3-hydroxymethylphthalimides, which have the potential for conversion into a number of other phenyl-substituted compounds. In this presentation, the transformation of the hydroxymethyl group to the corresponding chloride and the reactions of the benzylic halides with a variety of amines as nucleophiles will be described. With alkyl amines, nucleophilic acyl substitution at the imide ring competes with the desired alkyl substitution to yield diamides. Studies with substituted anilines show the rate of substitution varies markedly with the basicity of the nucleophile."
Fundamental investigation of substituent effects on threshold energy and electron density for the [1,3] thioallylic rearrangment by Mindy Schueneman, CU ANYL Chem 1st Year, Jimenez group
"Computational chemistry provides information of reaction energetics, thermodynamics, and kinetics by integrating computer modelling and and chemical theory. Computational chemistry was used to examine the effect of electron withdrawing and donating groups on both the threshold energy and electron density for the [1,3] thioallylic rearrangement mechanism. Thioallyl compounds contain a 3 carbon allyl chain with a sulfur in the C1 position. Through the combination of DFT and QTAIM, two computational methods, it was found that the thioallylic mechanism undergoes a concerted transition state, with most of the electron density contained on the sulfur atom. In addition, the activation energy barrier was found to decrease with the addition of electron donating groups located at various parts on the allyl backbone."