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Hirshfeld and DFT analysis of the N‐heterocyclic carbene proligand methylenebis( N ‐butylimidazolium) as the acetonitrile‐solvated diiodide salt
Author(s) -
Cebollada Andrea,
Vellé Alba,
Sanz Miguel Pablo J.
Publication year - 2016
Publication title -
acta crystallographica section c
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.304
H-Index - 17
ISSN - 2053-2296
DOI - 10.1107/s2053229616006781
Subject(s) - acetonitrile , chemistry , iodide , bromide , carbene , salt (chemistry) , medicinal chemistry , solvent , catalysis , methylene , hydrogen bond , density functional theory , crystal structure , crystallography , inorganic chemistry , organic chemistry , computational chemistry , molecule
N‐Heterocyclic carbene (NHC) based systems are usually exploited in the exploration of catalytic mechanisms and processes in organocatalysis, and homo‐ and heterogeneous catalysis. However, their molecular structures have not received adequate attention. The NHC proligand methylenebis( N ‐butylimidazolium) has been synthesized as the acetonitrile solvate of the diiodide salt, C 15 H 26 N 4 2+ ·2I − ·CH 3 CN [1,1′‐methylenebis(3‐butylimidazolium) diiodide acetonitrile monosolvate], and fully characterized. An interesting cation–anion connection pattern has been identified in the crystal lattice, in which three iodide anions interact simultaneously with the cisoid ‐oriented cation. A Hirshfeld surface analysis reveals the predominance of hydrogen bonding over anion–π interactions. This particular arrangement is observed in different methylene‐bridged bis(imidazolium) cations bearing chloride or bromide counter‐anions. Density functional theory (DFT) calculations with acetonitrile as solvent reproduce the geometry of the title cation.