Thermal Interconversions of the C 16 H 10  Cyclopenta‐Fused Polycyclic Aromatic Hydrocarbons Fluoranthene, Acephenanthrylene and Aceanthrylene Revisited | Zendy

Sarobe Martin | Zendy; Jenneskens Leonardus W. | Zendy; Wesseling Jolanda | Zendy; Snoeijer Judith D. | Zendy; Zwikker Jan W. | Zendy

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Thermal Interconversions of the C 16 H 10 Cyclopenta‐Fused Polycyclic Aromatic Hydrocarbons Fluoranthene, Acephenanthrylene and Aceanthrylene Revisited

Author(s) -

Sarobe Martin,

Jenneskens Leonardus W.,

Wesseling Jolanda,

Snoeijer Judith D.,

Zwikker Jan W.

Publication year - 1997

Publication title -

liebigs annalen

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.825

H-Index - 155

eISSN - 1099-0690

pISSN - 0947-3440

DOI - 10.1002/jlac.199719970624

Subject(s) - fluoranthene , chemistry , thermal decomposition , pyrolysis , thermal stability , methylene , decomposition , medicinal chemistry , photochemistry , organic chemistry , anthracene

The thermal interconversion of the C 16 H 10 cyclopenta‐fused polycyclic aromatic hydrocarbons (CP‐PAH) fluoranthene ( 1 ), acephenanthrylene ( 2 ) and aceanthrylene ( 3 ) has been studied using Flash Vacuum Thermolysis (FVT). In contrast to previously reported flow‐pyrolysis results, which gave the unexpected thermodynamic stability order 1 > 3 > 2 , FVT temperature‐conversion data unequivocally show the expected order 1 > 2 > 3 . These results are supported by independent FVT experiments with 9‐ethynylphenanthrene ( 4 ), 9‐ethynylanthracene ( 5 ) and 5‐(anthryl‐9′‐methylene)‐2,2‐dimethyl‐1,3‐dioxan‐4,6‐dione ( 6 ), which are precursors for acephenanthrylene ( 2 ) and aceanthrylene ( 3 ), respectively. The interpretation of the FVT results is corroborated by semiempirical AM1 calculations of the C 16 H 10 potential energy surface.

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