Takudrei

223
[N•••I+•••N] Halogen-Bonded Dimeric Capsules from Tetrakis(3-pyridyl)ethylenecavitands

L. Turunen, U. Warzok, R. Puttreddy, N.K. Beyeh, C.A.Schalley, K. Rissanen— 2016

Two [N···I+···N] halogen-bonded dimeric capsules using tetrakis(3-pyridyl)ethylenecavitands with different lower rim alkyl chains are synthesized and analyzed in solution and the gas phase. These first examples of symmetrical dimeric capsules making use of the iodonium ion (I+) as the main connecting module are characterized by 1H NMR spectroscopy, diffusion ordered NMR spectroscopy (DOSY), electrospray ionization mass spectrometry (ESI-MS) and ion mobility-mass spectrometry (TW-IMS) experiments. The synthesis and effective halogen-bonded dimerization proceeds through analogous dimeric capsules with [N···Ag+···N] binding motifs as the intermediates as evidenced by the X-ray structures of (CH2Cl2)2@[3a2∙Ag4∙(H2O)2∙OTs4] and (CH2Cl2)2@[3a2∙Ag4∙(H2O)4∙OTs4], two structurally different capsules.

Title223
[N•••I+•••N] Halogen-Bonded Dimeric Capsules from Tetrakis(3-pyridyl)ethylenecavitands
AuthorL. Turunen, U. Warzok, R. Puttreddy, N.K. Beyeh, C.A.Schalley, K. Rissanen
Date20161006
IdentifierDOI: 10.1002/anie.201607789
Source(s)
CitationAngew. Chem. Int. Ed. 2016, 55, 14033-14036
TypeText