Bent and twisted: the electronic structure of 2-azapropenylium ions obtained by guanidine oxidation
New bis-2-azapropenylium ions are obtained by oxidation of guanidino-substituted aromatic compounds. The dications 12+ (1 = 1,4-bis-tetramethylguanidinobenzene) and 22+ (2 = 1,4-bis-guanidinobenzene) exhibit unexpected bent-twisted structures, that differ from the known 2-azapropenylium ion structur...
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| Main Authors: | , , , |
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| Format: | Article (Journal) |
| Language: | English |
| Published: |
20 Apr 2016
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| In: |
RSC Advances
Year: 2016, Volume: 6, Issue: 45, Pages: 39323-39329 |
| ISSN: | 2046-2069 |
| DOI: | 10.1039/C6RA04494H |
| Online Access: | Verlag, lizenzpflichtig, Volltext: https://doi.org/10.1039/C6RA04494H Verlag, lizenzpflichtig, Volltext: https://pubs.rsc.org/en/content/articlelanding/2016/ra/c6ra04494h 
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| Author Notes: | Julius Hornung, Olaf Hübner, Elisabeth Kaifer, Hans-Jörg Himmel |
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| 520 | |a New bis-2-azapropenylium ions are obtained by oxidation of guanidino-substituted aromatic compounds. The dications 12+ (1 = 1,4-bis-tetramethylguanidinobenzene) and 22+ (2 = 1,4-bis-guanidinobenzene) exhibit unexpected bent-twisted structures, that differ from the known 2-azapropenylium ion structures (linear-orthogonal 2-azaallenium ion or bent-planar 2-azaallylium ion), and resemble the structures of carbodicarbenes. Their electronic structure was analysed by a combination of experiments and quantum chemical calculations. The results indicate that the bent-planar structure is disfavoured for steric reasons, while the allene-type linear-orthogonal structure is also disfavoured due to the electron-donating groups that support the bent form. For these reasons a bent-twisted structure is adopted, in which the nitrogen atom is engaged with two different orbitals in π-bonding with the carbon π-system and in a weaker π-interaction with the CN2 group of the guanidino system. | ||
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