Short Intramolecular Hydrogen Bonds Derivatives of Malonaldehyde with Symmetrical Substituents
Date of Award
2007
Document Type
Thesis
Degree Name
Bachelors
Department
Natural Sciences
First Advisor
Walstrom, Katherine
Keywords
Density Functional Theory, Computational Chemistry, B3LYP
Area of Concentration
Chemistry
Abstract
A systematic density functional theory study of various derivatives of malonaldehyde to explore very short hydrogen bonds (roo < 2.450 A) has been carried out. Various electron withdrawing groups, including CN, NO2, and BH2, have been attached to the unique carbon. To the two equivalent carbons, a strong electron donor and/or sterically hindered substituent, including but not limited to NH2, N(CH3)2, and C(CH3)3, was used to strengthen the intramolecular hydrogen bond. Six molecules were found to have extremely short intramolecular hydrogen bonds. Three of the most interesting molecules have dimethylamines substituted on the symmetrical carbons with a strong electron withdrawing group bonded to the unique carbon. This research explored compounds that could possibly influence biological reactions. This study also displayed a systematic study of organic trends comparing electron withdrawing and donation effects and steric hindrance.
Recommended Citation
Hargis, Jacqueline, "Short Intramolecular Hydrogen Bonds Derivatives of Malonaldehyde with Symmetrical Substituents" (2007). Theses & ETDs. 3797.
https://digitalcommons.ncf.edu/theses_etds/3797