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Internet Electronic Journal of Molecular Design - IEJMD, ISSN 1538-6414, CODEN IEJMAT
| ABSTRACT - Internet Electron. J. Mol. Des. December 2003, Volume 2, Number 12, 783-797 |
Ab initio MO Studies of the Mutagenic Properties of Allylic Chloropropenes
Hiroyuki Shinoda, Michio Sayama, Yoshihiro Mori, and Keiichi Kawano
Internet Electron. J. Mol. Des. 2003, 2, 783-797
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Abstract:
It has become clear that there are two metabolic pathways
involved in the mutagenic activation of chloropropenes by S9
mix. It is also clear that the dominant pathway depends upon the
substituted positions of chlorine atoms. We investigated the
relationship between the mutagenic activity of chloropropenes
and their electronic structures as obtained by molecular orbital
calculations. The calculations of charge densities were performed
for some correlation levels, such as MP4SDQ/6-31G** and
MP3/6-31++G**. Moreover, the charge densities were calculated
by the CHELPG method for MP2/6-31G** level. Furthermore, a
fully optimized calculation of protonated species was also
performed. The charge densities calculated by Mulliken's
approximation could not explain the experimental results
regarding the mutagenic activities of the epoxidative metabolic
pathway. On the other hand, the CHELPG charge densities
showed good correspondence to the experimental results for the
mutagenic activities. With compounds other than 2,3-dichloropropene,
the calculation of protonated chloropropenes
showed that the HCl molecule became detached and allylic
cation was produced. It is thought that the metabolic pathways of
chloropropenes depend partly on the electronic structure of
chloropropenes and partly on the electronic structure of
subsequent intermediate compounds.
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