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- Title
Stable Diporphyrinylaminyl Radical and Nitrenium Ion.
- Authors
Shimizu, Daiki; Fujimoto, Keisuke; Osuka, Atsuhiro
- Abstract
Abstract: Nitrenium ions, isoelectronic nitrogen counterparts of carbenes, are important intermediates in various biological and chemical processes. Herein we describe the first synthesis and characterization of a stable nitrenium ion without resonance stabilization by adjoining amino groups. Namely, a stable salt of a diporphyrinylnitrenium ion was synthesized by stepwise oxidation of the corresponding diporphyrinylamine through a stable aminyl radical. The nitrenium ion exhibits characteristic features such as a singlet ground state, enhanced double‐bond character of the central C−N bonds, no reactivity toward water and methanol, and negative solvatochromic behavior.
- Subjects
NITRENIUM ions; ISOELECTRONIC sequences; SOLVATOCHROMISM; RADICAL cations; AMINO group
- Publication
Angewandte Chemie, 2018, Vol 130, Issue 30, p9578
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.201805385