Diamidocarbene-Based Thiele and Tschitschibabin Hydrocarbons: Carbonyl Functionalized Kekulé Diradicaloids

Herein, we report diamidocarbene (DAC)-based Thiele and Tschitschibabin hydrocarbons, diradicaloids that contain four carbonyl/amido functional groups. The impact of two different π-conjugated spacers, p-phenylene vs p,p′-biphenylene, has been realized. The quantum chemical calculations suggest diam...

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Bibliographic Details
Published in:Journal of organic chemistry 2021-12, Vol.86 (23), p.16464-16472
Main Authors: Maiti, Avijit, Sobottka, Sebastian, Chandra, Shubhadeep, Jana, Debayan, Ravat, Prince, Sarkar, Biprajit, Jana, Anukul
Format: Article
Language:English
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Summary:Herein, we report diamidocarbene (DAC)-based Thiele and Tschitschibabin hydrocarbons, diradicaloids that contain four carbonyl/amido functional groups. The impact of two different π-conjugated spacers, p-phenylene vs p,p′-biphenylene, has been realized. The quantum chemical calculations suggest diamidocarbene (DAC)-based Thiele hydrocarbon (p-phenylene bridged) closed-shell singlet is the ground state, whereas for the diamidocarbene (DAC)-based Tschitschibabin hydrocarbon (p,p′-biphenylene bridged), open-shell singlet is the ground state. The influence of two different π-conjugated spacers also has been reflected in their UV–vis spectra. To gain more information on the diamidocarbene (DAC)-based Thiele and Tschitschibabin hydrocarbons, we have also carried out cyclic voltammetry investigations along with UV–vis–NIR-spectroelectrochemical studies of their corresponding 2-e oxidized product.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.1c01827