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Volumn 11, Issue 12, 2009, Pages 2623-2626

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

(9) Shackelford, Scott A a Belletire, John L a Boatz, Jerry A a Schneider, Stefan a Wheaton, Amanda K a Wight, Brett A a Hudgens, Leslie M a Ammon, Herman L b Strauss, Steven H c

a AIR FORCE RESEARCH LABORATORY (United States)

b University of Maryland (United States)

c Department of Ecosystem Science and Sustainability (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 67149093412 PISSN: 15237060 EISSN: None Source Type: Journal
DOI: 10.1021/ol900550v Document Type: Article

Times cited : (21)

References (18)

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4
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- U.S. Patent 7 521 564
- Shackelford, S. A. U.S. Patent 7 521 564, 2009.
- (2009)
- Shackelford, S.A.¹

5
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- and references therein
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- Grimes, R.N.¹

8
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- and references therein, (b) Muetterties, E. L.; Knoth, W. H. Polyhedral Boranes: M. Dekker: New York, 1969.
- and references therein, (b) Muetterties, E. L.; Knoth, W. H. Polyhedral Boranes: M. Dekker: New York, 1969.

9
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10
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- Larsen, A. S.; Holbrey, J. D.; Tham, F. S.; Reed, C. A. J. Am. Chem. Soc. 2000, 122, 7264,
- (2000) J. Am. Chem. Soc , vol.122 , pp. 7264
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11
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- Zhu, Y.; Ching, C.; Carpenter, K.; Xu, R.; Selvaratnam, S.; Hosmane, N. S.; Maguire, J. A. Appl. Organometal. Chem 2003, 17, 346.
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- Zhu, Y.¹ Ching, C.² Carpenter, K.³ Xu, R.⁴ Selvaratnam, S.⁵ Hosmane, N.S.⁶ Maguire, J.A.⁷

12
- 84868974787
- - reactants were purchased from Katchem Ltd., E. Krasnohorske 6, 110 00 Prague 1, Czech Republic and were used as received,
- - reactants were purchased from Katchem Ltd., E. Krasnohorske 6, 110 00 Prague 1, Czech Republic and were used as received,

13
- 84868980982
- Depending upon the salt product solubility, some heterocyclium salts immediately precipitate; in other cases, the desired heterocyclium salt crystallizes overnight at +3.5 °C.
- Depending upon the salt product solubility, some heterocyclium salts immediately precipitate; in other cases, the desired heterocyclium salt crystallizes overnight at +3.5 °C.

14
- 84868974782
- 4-Amino-l-methyl-1,2,4-triazolium]2[closo-B 12H12, 1: Solid[4-Amino-l-methyl-1,2,4-triazolium] iodide (4.52 g; 20.00 mmol, CH3I methylated plus recrystallization from methanol) and commercial K2[closo-B12H 12, 2.20 g; 10.00 mmol) were placed into a 50 mL beaker. To this was added 18.0 mL DI water. The contents were stirred and heated at gentle reflux for 4 min. The resulting clear tan solution was cooled overnight in a refrigerator and off-white crystals deposited. Filtration and rinsing the filter-cake with 2 × 1.0 mL portions of pre-chilled DI water followed. The crystals were dried under high vacuum to give anhyd spectroscopically pure salt product by 1H NMR (3.096 g: 91.05, Recrystallization of a portion (1.04 g) was conducted in 40.0 mL boiling DI water containing 5 mL anhydrous methanol. Most of the methanol boiled off. The resulting clear solution was cooled overnight in
- -1; X-ray in Figure 3 and Supporting Information.

15
- 84868985607
- 1-Amino-3-H-1,2,3-triazolium][closo-CB12H 12, 9: Solid [1-Amino-3-H-1,2,3-triazolium] chloride (2.41 g; 20.00 mmol) and commercial K[closo-CB11H12, 3.64 g; 20.01 mmol) are placed into a 50 mL Pyrex beaker. Addition of 10.0 mL DI water was followed by heating to gentle reflux and then pouring the nearly clear solution into a fresh 50 mL Pyrex beaker leaving behind a small amount of a water insoluble impurity in the K[B11H12, reactant. The reaction mixture was cooled overnight in the refrigerator (3.5 °C) to effect crystallization. Filtration, rinsing the filter-cake with 2.0 mL of pre-chilled DI water, and pumping at high vacuum (60 mTorr) gave a 4.59 g of solid with some entrained water. Two recrystallizations from 7.0 mL refluxing DI water gave 2.51 g of pure salt; overall purified yield (two recrystallizations, 54.9, ′H NMR 400 MHz, std. DMSO-d6 (2.50, δ 8.71 brs, 3H
- - m/z = 143.2035, found 143.2045.

16
- 54949121780
- Ammon, H. L. Propellants, Explos., Pyrotech. 2008, 33. 92.
- (2008) Propellants, Explos., Pyrotech , vol.33 , pp. 92
- Ammon, H.L.¹

17
- 84868974777
- 2O molecules for salt 3. Both salts become amorphorus powders when the solvent molecules are removed for pycnometry density analyses.
- 2O molecules for salt 3. Both salts become amorphorus powders when the solvent molecules are removed for pycnometry density analyses.

18
- 84868980979
- Our DSC analyses of salt 11 (1 °C/min) show a small endotherm at 128 °C, which we attribute to a solid phase transition, and a larger endotherm at 175-176 °C. This latter temperature matches the visually-determined melting point where a white solid changes to a colorless liquid. Visually-determined solid softening occurs from 106-132 °C
- Our DSC analyses of salt 11 (1 °C/min) show a small endotherm at 128 °C, which we attribute to a solid phase transition, and a larger endotherm at 175-176 °C. This latter temperature matches the visually-determined melting point where a white solid changes to a colorless liquid. Visually-determined solid softening occurs from 106-132 °C.

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