Spectrometry and reactivity of phenalenyl anions

Mark A. Hempenius; Wouter Heinen; Patrick P.J. Mulder; Cees Erkelens; Han Zuilhof; Johan Lugtenburg; Jan Cornelisse

doi:10.1002/poc.610070605

Spectrometry and reactivity of phenalenyl anions

Mark A. Hempenius, Wouter Heinen, Patrick P.J. Mulder, Cees Erkelens, Han Zuilhof, Johan Lugtenburg, Jan Cornelisse^*

^*Corresponding author for this work

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

13 Citations (Scopus)

Abstract

The aromatic odd‐alternant phenalenyl anion and a number of its derivatives were prepared in order to study the perturbation of this conjugated anion by methyl and methoxy groups. The conjugated anions were studied by means of ¹H and ¹³C NMR spectrometry, alkylation experiments and semi‐empirical calculations. It was found that a substituent at a charged carbon atom perturbs the entire conjugated system, whereas substituents at inactive (uncharged) carbon atoms have a large effect on the positions ortho to the substituent.

Original language	English
Pages (from-to)	296-302
Number of pages	7
Journal	Journal of physical organic chemistry
Volume	7
Issue number	6
DOIs	https://doi.org/10.1002/poc.610070605
Publication status	Published - Jun 1994
Externally published	Yes

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AU - Hempenius, Mark A.

AU - Heinen, Wouter

AU - Mulder, Patrick P.J.

AU - Erkelens, Cees

AU - Zuilhof, Han

AU - Lugtenburg, Johan

AU - Cornelisse, Jan

PY - 1994/6

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AB - The aromatic odd‐alternant phenalenyl anion and a number of its derivatives were prepared in order to study the perturbation of this conjugated anion by methyl and methoxy groups. The conjugated anions were studied by means of 1H and 13C NMR spectrometry, alkylation experiments and semi‐empirical calculations. It was found that a substituent at a charged carbon atom perturbs the entire conjugated system, whereas substituents at inactive (uncharged) carbon atoms have a large effect on the positions ortho to the substituent.

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Spectrometry and reactivity of phenalenyl anions

Abstract

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