Applications of Molecular Modeling to Transition State Energies and Conformations

Abstract

A quantitative model of Baldwin's Rules for Ring Closure is constructed. Specific system of interest are the lactonization and intramolecular Michael addition. A simulated transition state for each of these reactions is determined for simplified intermolecular systems. The intermolecular system for lactonization is the attack of water on pronate formic acid. The intermolecular system for the Michael addition is the attack of water on protonated acrylic acid. These transition state geometries are determined at the AMI semi-empirical level. Results of these geometries are combined with force constant determined in this research to produce a molecular mechanics model for these transition states. Reactivity determinations made using this model for competitive lactonizations and intramolecular Michael additions are acceptable. A strain energy cutoff range for Baldwin Rule 5-Endo-Trig has been determined to be between 63.9 and 80.4 kcal/mol. Chemistry - numerical solutions; Organiz compounds - synthetic; Chemistry; Organic; Molecules.

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Document Details

Document Type
Technical Report
Publication Date
May 08, 1992
Accession Number
ADA257130

Entities

People

  • John C. Mohs

Organizations

  • United States Naval Academy

Tags

DTIC Thesaurus Topics

  • Acids
  • Acrylic Acid
  • Central Processing Units
  • Chemical Compounds
  • Chemical Reactions
  • Chemistry
  • Computational Chemistry
  • Computational Science
  • First Principles Calculations
  • Geometry
  • Heat Of Formation
  • Mechanics
  • Molecular Orbital Theory
  • Organic Chemistry
  • Physical Chemistry
  • Three Dimensional
  • United States Naval Academy

Fields of Study

  • Chemistry

Readers

  • Organic Chemistry
  • Quantum Chemistry
  • Surface Coatings Technology.