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Theoretical structure-activity study of mutagenic allyl chlorides
1Department of Chemistry, Southeastern Massachusetts University, North Dartmouth 02747.
Chemical Research in Toxicology
|May 1, 1991
Summary
Computational chemistry reveals that mutagenic allyl chlorides primarily act via SN1 reactions, forming allylic cations that damage DNA. Carbocation stability and charge delocalization predict mutagenicity.
Area of Science:
- Computational chemistry
- Molecular modeling
- Toxicology
Background:
- Allyl chlorides are known mutagens.
- The precise mechanism of their mutagenic action requires further elucidation.
Purpose of the Study:
- To clarify the mutagenic mechanism of substituted allyl chlorides.
- To correlate computed molecular properties with experimental mutagenic potentials.
Main Methods:
- Ab initio molecular orbital calculations using STO-3G and 3-21G levels.
- Comparison of computed molecular properties with experimental data.
Main Results:
- Computational results support an SN1 reaction mechanism involving allylic cation formation.
- Allylic carbocation stability and charge delocalization correlate well with observed mutagenicity.
- Computed properties show potential for estimating alkylating activity and mutagenicity.
Conclusions:
- The primary mutagenic mechanism involves SN1 formation of reactive allylic cations.
- Molecular orbital calculations are valuable tools for predicting mutagenicity of allyl compounds.