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[2+2] Cycloaddition Products of Tetradehydrodianthracene: Experimental and Theoretical Proof of Extraordinary Long CC Single Bonds
Author(s) -
Kammermeier Stefan,
Herges Rainer,
Jones Peter G.
Publication year - 1997
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.199717571
Subject(s) - single bond , chemistry , bond , cycloaddition , raman spectroscopy , triple bond , force constant , double bond , computational chemistry , molecule , physics , organic chemistry , optics , group (periodic table) , catalysis , finance , economics
An extremely long CC single bond of 1.713 Å is found in the [2+2] cycloadduct of ortho ‐didehydrobenzene and tetradehydrodianthracene. The force constant of this central bond is reduced to only 30% of that of the CC bond in ethane. The corresponding CC stretching vibration (687 cm −1 ) in the Raman spectrum is red‐shifted 300 cm −1 relative to the bands of “normal” hydrocarbons.