EPR Spectroscopy of Radical Ions of a 2,3-Diamino-1,4-naphthoquinone Derivative

Tarábek, Ján; Wen, Jin; Dron, Paul I.; Pospíšil, Lubomír; Michl, Josef

doi:10.1021/acs.joc.8b00398

Title: EPR Spectroscopy of Radical Ions of a 2,3-Diamino-1,4-naphthoquinone Derivative

Journal Article · Fri Apr 13 00:00:00 EDT 2018 · Journal of Organic Chemistry

DOI:https://doi.org/10.1021/acs.joc.8b00398· OSTI ID:1688393

^[1]; Wen, Jin ^[1]; Dron, Paul I. ^[2];

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Inst. of Organic Chemistry and Biochemistry, Prague (Czech Republic)
Univ. of Colorado, Boulder, CO (United States)
Inst. of Organic Chemistry and Biochemistry, Prague (Czech Republic); J. Heyrovský Inst. of Physical Chemistry, Prague (Czech Republic)
Inst. of Organic Chemistry and Biochemistry, Prague (Czech Republic); Univ. of Colorado, Boulder, CO (United States)

We report the electron paramagnetic resonance spectra of the radical cation and radical anion of 1,2,2,3-tetramethyl-2,3-dihydro-1H-naphtho[2,3-d]imidazole-4,9-dione (1) and its doubly ¹³C labeled analogue 2, of interest for singlet fission. The hyperfine coupling constants are in excellent agreement with density functional theory calculations and establish the structures beyond doubt. Unlike the radical cation 1^•+, the radical anion 1^•– and its parent 1 have pyramidalized nitrogen atoms and inequivalent methyl groups 15 and 16, in agreement with the calculations. The distinction is particularly clear with the labeled analogue 2^•–.

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Research Organization:: Univ. of Colorado, Boulder, CO (United States)

Sponsoring Organization:: USDOE Office of Science (SC), Basic Energy Sciences (BES); Grant Agency of the Czech Republic; Academy of Sciences of the Czech Republic

Grant/Contract Number:: SC0007004

OSTI ID:: 1688393

Journal Information:: Journal of Organic Chemistry, Vol. 83, Issue 10; ISSN 0022-3263

Publisher:: American Chemical SocietyCopyright Statement

Country of Publication:: United States

Language:: English

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Cited by: 6 works

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Synthesis of Amino Acid–Naphthoquinones and In Vitro Studies on Cervical and Breast Cell Lines Rivera-Ávalos, Ernesto; de Loera, Denisse; Araujo-Huitrado, Jorge Gustavo Molecules, Vol. 24, Issue 23 https://doi.org/10.3390/molecules24234285	journal	November 2019

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