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Open AccessArticle

Time-Resolved Spectroscopic Study of N,N-Di(4-bromo)nitrenium Ions in Selected Solutions

by Lili Du 1,2,†, Xin Lan 1,†, Zhiping Yan 1, Ruixue Zhu 1,3 and David Lee Phillips 1,*
Department of Chemistry, The University of Hong Kong, Hong Kong S.A.R., China
Institute of Life Sciences, Jiangsu University, Zhenjiang 212013, China
School of Physical Science and Technology, Shanghai Tech University, Shanghai 201210, China
Author to whom correspondence should be addressed.
These authors contributed equally to this work.
Academic Editor: Chong Fang
Molecules 2018, 23(12), 3182;
Received: 8 November 2018 / Revised: 26 November 2018 / Accepted: 30 November 2018 / Published: 3 December 2018
(This article belongs to the Special Issue Vibrational Probes of Biomolecular Structure and Dynamics)
Nitrenium ions are important reactive intermediates in chemistry and biology. In this work, femtosecond and nanosecond transient absorption (fs-TA and ns-TA) along with nanosecond time-resolved resonance Raman (ns-TR3) experiments were employed to examine the photochemical pathways of N-(4,4′-dibromodiphenylamino)-2,4,6-trimethylpyridinium BF4 (salt (DN) from just absorption of a photon of light to the production of the important N,N-di(4-bromophenyl)nitrenium ion 2. In acetonitrile (MeCN), the formation of halogenated diarylnitrenium ion 2 was observed within 4 ps, showing the vibrational spectra with strong intensity. The nucleophilic adduct reaction of ion 2 with H2O was also examined in aqueous solutions. The direct detection of the unique ortho adduct intermediate 3 shows that there is an efficient and exclusive reaction pathway for 2 with H2O. The results shown in this paper give new characterization of 2, which can be used to design time-resolved spectroscopy investigations of covalent addition reactions of nitrenium ions with other molecules in future studies. View Full-Text
Keywords: nitrenium ion; resonance Raman; transient absorption; reactive intermediate nitrenium ion; resonance Raman; transient absorption; reactive intermediate
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MDPI and ACS Style

Du, L.; Lan, X.; Yan, Z.; Zhu, R.; Phillips, D.L. Time-Resolved Spectroscopic Study of N,N-Di(4-bromo)nitrenium Ions in Selected Solutions. Molecules 2018, 23, 3182.

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