Nitrosonium complexes of [2.2]paracyclophane

Nitrosonium complexes of [2.2]paracyclophane Full article

Journal

Russian Journal of Organic Chemistry
ISSN: 1070-4280 , E-ISSN: 1608-3393

Output data

Year: 2006, Volume: 42, Number: 3, Pages: 406-411 Pages count : DOI: 10.1134/S1070428006030122

Authors

Borodkin GI , Elanov IR , Andreev RV , Shakirov MM , Shubin VG

Affiliations

1	(Данные Web of science) Russian Acad Sci, Vorozhtsov Novosibirsk Inst Organ Chem, Siberian Div, Novosibirsk 630090, Russia

The reaction of [2.2]paracyclophane with nitrosonium tetrachloroaluminate was studied by NMR (H-1, C-13) spectroscopy using deuterium isotopic perturbation technique. The resulting cationic complexes containing one and two nitrosonium ions are involved in fast (on the NMR time scale) interconversion. Quantum-chemical calculations performed on the DFT level (using triple zeta basis set) indicate the higher stability of 2 eta single-charged pi-complexes relative to sigma complexes corresponding to the addition of NO+ ion at the ipso and ortho positions. The formation of the single-charged pi-complex is energetically more favorable, compared to the double-charged pi-complex. The affinity of NO+ for [2.2]paracyclophane is much greater than for p-xylene, presumably due to stacking interaction between the aromatic rings in the pi-complex.

Borodkin G. , Elanov I. , Andreev R. , Shakirov M. , Shubin V.
Nitrosonium complexes of [2.2]paracyclophane
Russian Journal of Organic Chemistry. 2006. V.42. N3. P.406-411. DOI: 10.1134/S1070428006030122 WOS Scopus РИНЦ OpenAlex

Бородкин Г.И. , Еланов И.Р. , Андреев Р.В. , Шакиров М.М. , Шубин В.Г.
Нитрозониевые комплексы [2.2]парациклофана
Журнал органической химии (RUSS J ORG CHEM+). 2006. Т.42. №3. С.418-423. РИНЦ

Published print:

Mar 1, 2006

Web of science:	WOS:000236723700012
Scopus:	2-s2.0-33645798375
Elibrary:	13511445
OpenAlex:	W2002582560

DB	Citing
Web of science	8
Scopus	7
Elibrary	7
OpenAlex	6