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.

Rights

This bibliographic record is available under the Creative Commons CC0 public domain dedication. The New College of Florida, as creator of this bibliographic record, has waived all rights to it worldwide under copyright law, including all related and neighboring rights, to the extent allowed by law.

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