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Calculated properties of some possible vinyl chloride metabolites
Author(s) -
Politzer Peter,
Proctor Timothy R.
Publication year - 1982
Publication title -
international journal of quantum chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.484
H-Index - 105
eISSN - 1097-461X
pISSN - 0020-7608
DOI - 10.1002/qua.560220610
Subject(s) - carbonium ion , chemistry , protonation , epoxide , vinyl chloride , chlorine , chloride , double bond , computational chemistry , ab initio , acetyl chloride , medicinal chemistry , photochemistry , ion , organic chemistry , polymer chemistry , catalysis , polymer , copolymer
Abstract There is considerable evidence indicating that the carcinogenic action of vinyl chloride involves metabolic conversion to the epoxide (chlorooxirane) as the initial step. In order to learn more about its subsequent behavior, we have computed structures, energies and other properties for two different protonated forms of the epoxide, and also for two possible rearrangement products, chloroacetaldehyde and acetyl chloride. An ab initio SCF ‐ MO procedure (GAUSSIAN 70) was used. Oxygen protonation is found to weaken both CO bonds, the effect being greater for the bond involving the carbon bearing the chlorine. Chlorine protonation leads to a marked weakening of the CCl bond; this suggests a possible loss of HCl, leaving behind a carbonium ion (and possible alkylating agent or rearrangement precursor). Thus, while CO bond breaking is doubtless an important reaction pathway for chlorooxirane, our results indicate that attention should also be focused upon the CCl bond; its rupture may conceivably be a key step in the biological action of vinyl chloride.