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The Radical Cation of N,N ′‐Tetramethylene‐ syn ‐1,6:8,13‐diimino[14]annulene. An Experimental Study of the NN Three‐Electron σ Bond
Author(s) -
Gerson Fabian,
Gescheidt Georg,
Buser Urs,
Vogel Emanuel,
Lex Johann,
Zehnder Margareta,
Riesen Andreas
Publication year - 1989
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.198909021
Subject(s) - annulene , radical ion , chemistry , bond length , electron , crystallography , medicinal chemistry , stereochemistry , ion , crystal structure , physics , organic chemistry , quantum mechanics
The direct detection of an NN three‐electron σ‐bond in the system 1 / 1 ⊕ ClO 4 ⊖was possible by X‐ray structure analysis. The NN distance of 256.0 pm in 1 is shortened to 218.9 pm in the radical cation 1 ⊕ . Hitherto, such a detection in this way was only possible in the case of the radical cations of 1,6‐diazabicyclo[4.4.4]tetradecane and N,N ″‐trimethylene‐ syn ‐1,6:8,13‐diimino[14]annulene.