DENSITY FUNCTIONAL THEORETICAL STUDY OF NITRATED POLYCYCLIC AROMATIC HYDROCARBONS

Abstract

Nitro-polycyclic aromatic hydrocarbons (nitro-PAHs) are well-known mutagens. Correlations between the orientation of the nitro group relative to the plane of the aromatic ring and mutagenic effects of nitro-PAHs have been proposed. Synthesis of specific isomers of nitro-PAHs and elucidation of their crystal structure is required to establish the validity of the structure-function relationships. Such studies are scarce. Fortunately, electronic structure calculations can be readily done. In this study we have used density functional theory calculations to predict structure of nitro-PAHs, including 1-, 2-nitronaphthalenes; 1-, 2-, 9-nitroanthracenes; 1-, 2-, 3-, 4-, 9-nitrophenanthrenes; 1-, 2-, 4-nitropyrenes; and 6-nitrochrysene. The relationships between the calculated structures and the mutagenicity reported in the chemical literature are discussed.

Keywords:

• biological activity
• density functional theory
• mutagenicity
• nitrated polycyclic aromatic hydrocarbons
• nitro group orientation

The authors acknowledge financial support from the Ohio State Environmental Molecular Science Institute, funded by the National Science Foundation (CHE-0090147, EMSI Program). They also thank the Ohio Supercomputer Center for generous allocations of computer time.

Notes

^a From Ref. 25.

^b From Ref. 25.

^c From Ref. 26.

^d From Ref. 27.

^a From Ref. 46, electron diffraction data from Ref. 28.

^b From Ref. 43, X-ray (liquid).

^c X-ray crystal data from (Cambridge Data Base).

^d From Ref. 47, electron diffraction data.

^e From Ref. 31, X-ray diffraction data.

^f From Ref. 33, X-ray diffraction data.

^g From Ref. 32, X-ray diffraction data.

^a From Ref. 40.

^b From Ref. 31.

^c From Ref. 16.

^e From Ref. 33, X-ray diffraction.

^f From Ref. 37.

^g From Ref. 48.

^h From Ref. 37.

ⁱ From Ref. 40.

^j From Ref. 38, dose = μ g/plate, result reported as net revertants/plate.

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