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On the Aromaticity and Acidity of 1-Hydroxy-4,5-benzotropylium Derivatives

preprint
submitted on 07.12.2020, 05:45 and posted on 08.12.2020, 12:54 by Takuya Kodama, Yuki Kawashima, Zhirong Deng, Mamoru Tobisu

The aromaticity of 1-hydroxy-4,5-benzotropylium was assessed based on experimental and theoretical investigations. An X-ray crystallographic analysis revealed a decrease of bond alternation in the seven-membered ring of 1-hydroxy-4,5-benzotropylium derivatives compared with that of the parent 4,5-benzotropones, which is indicative of an increase in aromaticity upon protonation. NICS and AICD calculation also supported the increased aromaticity of 1-hydroxy-4,5-benzotropylium. The pKa values for a series of 1-hydroxy-4,5-benzotropylium derivatives were also determined.

Funding

Development of catalytic molecular transformation reaction using metal troponoid complex

Japan Society for the Promotion of Science

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History

Email Address of Submitting Author

kodama@chem.eng.osaka-u.ac.jp

Institution

Osaka University

Country

Japan

ORCID For Submitting Author

0000-0001-8275-2393

Declaration of Conflict of Interest

The authors declare no competing financial interest.

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