Synthesis and structural, spectroscopic, and electrochemical characterization of benzo[c]quinolizinium and its 5-aza-, 6-aza, and 5,6-diaza analogues

Aleksandra Jankowiak, Emilia Obijalska, Piotr Kaszynski, Adam Pieczonka, Victor G. Young

Research output: Contribution to journalArticlepeer-review

6 Scopus citations

Abstract

Four heterocyclic salts 1a-d were prepared by Ca2+-assisted cyclization of fluoro derivatives 3, and investigated by spectroscopic (NMR and UV), electrochemical, and computational (DFT and MP2) methods. The mechanism for the formation of the cations was investigated at the DFT level of theory. 2-D NMR spectroscopy for 1[ClO4] in DMSOd6 aided with DFT results permitted the assignment of 1H and 13C NMR signals in cations 1. The molecular and crystal structures for 1a[ClO4] [C13H10ClNO4 triclinic, P-1, a=9.6517(12) , b=11.0470(13) , c=12.2373(15) , α=67.615(1)°, β=78.845(2)°, γ=87.559(2)°; V=1183.0(2) 3, Z=4] and 1d[ClO4] [C12H9ClN2O4 triclinic, P-1, a=5.9525(6) , b=8.3141(9) , c=12.2591(13) , α=73.487(1)°, β=83.814(1)°, γ=83.456(1)°; V=576.07(10) 3, Z=2] were determined by X-ray crystallography and compared with results of DFT and MP2 calculations. Electrochemical analysis gave the reduction potential order (1b>1c∼1d>1a), which is consistent with computational results.

Original languageEnglish (US)
Pages (from-to)3317-3327
Number of pages11
JournalTetrahedron
Volume67
Issue number19
DOIs
StatePublished - May 13 2011

Bibliographical note

Funding Information:
Financial support for this work was received from the Petroleum Research Funds ( PRF-47243-AC4 ) and NSF ( OISE 0532040 ).

Copyright:
Copyright 2011 Elsevier B.V., All rights reserved.

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