Pairing heterocyclic cations with closo-icosahedral borane and carborane anions. i. benchtop aqueous synthesis of binary triazolium and imidazolium salts with limited water solubility

Scott A Shackelford; John L Belletire; Jerry A Boatz; Stefan Schneider; Amanda K Wheaton; Brett A Wight; Leslie M Hudgens; Herman L Ammon; Steven H Strauss

doi:10.1021/ol900550v

Pairing heterocyclic cations with closo-icosahedral borane and carborane anions. i. benchtop aqueous synthesis of binary triazolium and imidazolium salts with limited water solubility

Org Lett. 2009 Jun 18;11(12):2623-6. doi: 10.1021/ol900550v.

Authors

Scott A Shackelford¹, John L Belletire, Jerry A Boatz, Stefan Schneider, Amanda K Wheaton, Brett A Wight, Leslie M Hudgens, Herman L Ammon, Steven H Strauss

Affiliation

¹ Air Force Research Laboratory, Propellants Branch (AFRL/RZSP), 10 East Saturn Boulevard, Edwards AFB, California 93524-7680, USA. scottshack@roadrunner.com

PMID: 19441856
DOI: 10.1021/ol900550v

Abstract

Ten new salts that pair triazolium and imidazolium cations with closo-icosahedral anions [B(12)H(12)](2-) and [CB(11)H(12)](-) were synthesized in water solvent using an open-air, benchtop method. These unreported [Heterocyclium](2)[B(12)H(12)] and [Heterocyclium][CB(11)H(12)] salts extend reports of [Imidazolium][CB(11)H(12)] and [Pyridinium][CB(11)H(12)] salts that were synthesized in anhydrous organic solvents under an inert atmosphere with glovebox or Schlenk techniques. Spectroscopic data, melting points, and densities are reported for each salt. Single-crystal X-ray structures are provided for the five new [B(12)H(12)](2-) salts.