Nichtplanare Doppelbindung in einem kristallinen Derivat von anti-Sesquinorbornen (anti-Tetracyclo[6.2.1.13,6.02,7]dodec-2(7)-en) |
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Authors: | Otto Ermer Claus-Dieter Bdecker |
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Institution: | Otto Ermer,Claus-Dieter Bödecker |
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Abstract: | Non-Planar Double Bond in a Crystalline Derivative of anti-Sesquinorbornene (anti-Tetracyclo6.2.1.13,6.02,7]dodec-2(7)-ene) The olefinic double bond of the title compound 2 has been observed by X-ray techniques to deviate from planarity by 13.2 (0.3)° (symmetric out-of-plane bending). Empirical force field calculations for the parent hydrocarbon 1 (anti-sesquinorbornene) give a much larger corresponding deviation of 35.6°. The calculated nonplanar double bond deformations in anti-sesquinorbornene 1 as well as in the syn-isomer 4 and other related olefins are a consequence of substantial widenings of the exocyclic C(sp3)–C(sp2–Csp3) angles when keeping the double bond planar. The considerable computational exaggeration of this novel out-of-plane bending mechanism is attributed to various possible force field deficiencies. |
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