Overcrowded enes of the tricycloindane-1,3-dione series: Interplay of twisting, folding and pyramidalization

John J. Stezowski; P. Ulrich Biedermann; Thomas Hildenbrand; John A. Dorsch; Craig J. Eckhardt; Israel Agranat

doi:10.1039/C39930000213

Overcrowded enes of the tricycloindane-1,3-dione series: Interplay of twisting, folding and pyramidalization

John J. Stezowski^*
, P. Ulrich Biedermann
, Thomas Hildenbrand
, John A. Dorsch
, Craig J. Eckhardt
, Israel Agranat

^*Corresponding author for this work

Institute of Chemistry

Research output: Contribution to journal › Article › peer-review

18 Scopus citations

Abstract

MNDO-PM3 calculations have revealed three low energy conformations for the overcrowded ene 2-(thioxanthen-9-ylidene)indane-1,3-dione 2, two of which, a syn-pyramidalized C_s conformer (yellow solvated crystals) and a C₁ folded-twisted conformer (orange unsolvated crystals), were characterized by single crystal X-ray diffraction techniques, and a C ₂ twisted, non-pyramidalized conformer, which may be present in the thermochromic deep-red crystals obtainable by sublimation at T > 140°C.

Original language	English
Pages (from-to)	213-215
Number of pages	3
Journal	Journal of the Chemical Society D: Chemical Communications
Issue number	3
DOIs	https://doi.org/10.1039/C39930000213
State	Published - 1993

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title = "Overcrowded enes of the tricycloindane-1,3-dione series: Interplay of twisting, folding and pyramidalization",

abstract = "MNDO-PM3 calculations have revealed three low energy conformations for the overcrowded ene 2-(thioxanthen-9-ylidene)indane-1,3-dione 2, two of which, a syn-pyramidalized Cs conformer (yellow solvated crystals) and a C1 folded-twisted conformer (orange unsolvated crystals), were characterized by single crystal X-ray diffraction techniques, and a C 2 twisted, non-pyramidalized conformer, which may be present in the thermochromic deep-red crystals obtainable by sublimation at T > 140°C.",

author = "Stezowski, \{John J.\} and Biedermann, \{P. Ulrich\} and Thomas Hildenbrand and Dorsch, \{John A.\} and Eckhardt, \{Craig J.\} and Israel Agranat",

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doi = "10.1039/C39930000213",

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AU - Stezowski, John J.

AU - Biedermann, P. Ulrich

AU - Hildenbrand, Thomas

AU - Dorsch, John A.

AU - Eckhardt, Craig J.

AU - Agranat, Israel

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AB - MNDO-PM3 calculations have revealed three low energy conformations for the overcrowded ene 2-(thioxanthen-9-ylidene)indane-1,3-dione 2, two of which, a syn-pyramidalized Cs conformer (yellow solvated crystals) and a C1 folded-twisted conformer (orange unsolvated crystals), were characterized by single crystal X-ray diffraction techniques, and a C 2 twisted, non-pyramidalized conformer, which may be present in the thermochromic deep-red crystals obtainable by sublimation at T > 140°C.

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Overcrowded enes of the tricycloindane-1,3-dione series: Interplay of twisting, folding and pyramidalization

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