Accession Number : ADA257130


Title :   Applications of Molecular Modeling to Transition State Energies and Conformations


Descriptive Note : Final rept. 1991-1992


Corporate Author : NAVAL ACADEMY ANNAPOLIS MD


Personal Author(s) : Mohs, John C


Full Text : https://apps.dtic.mil/dtic/tr/fulltext/u2/a257130.pdf


Report Date : 08 May 1992


Pagination or Media Count : 80


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.


Descriptors :   *SYNTHESIS(CHEMISTRY) , *AROMATIC COMPOUNDS , CLOSURES , MODELS , ENERGY , RINGS , FORMIC ACID , ADDITION , ACRYLIC ACID , DETERMINATION , MECHANICS , REACTIVITIES , MOLECULES , ATTACK


Subject Categories : Organic Chemistry
      Physical Chemistry


Distribution Statement : APPROVED FOR PUBLIC RELEASE