Crystal Structure of 2-Ethylimidazole-1-sulfonyl Azide: A New Azidation Reagent

doi:10.3390/cryst2010118

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Crystals 2012, 2(1), 118-126; doi:10.3390/cryst2010118

Article

Crystal Structure of 2-Ethylimidazole-1-sulfonyl Azide: A New Azidation Reagent

Gerhard Laus¹, Verena Adamer¹, Michael Hummel¹, Volker Kahlenberg², Klaus Wurst¹, Sven Nerdinger³ and Herwig Schottenberger^1,*

¹ Faculty of Chemistry and Pharmacy, University of Innsbruck, 6020 Innsbruck, Austria ² Institute of Mineralogy and Petrography, University of Innsbruck, 6020 Innsbruck, Austria ³ Sandoz GmbH, 6250 Kundl, Austria

* Author to whom correspondence should be addressed.

Received: 4 January 2012; in revised form: 21 February 2012 / Accepted: 29 February 2012 / Published: 12 March 2012

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Abstract: Crystalline 2-ethylimidazole-1-sulfonyl azide was designed as a convenient reagent with improved thermal stability for electrophilic azidation of carbanions. The compound crystallized in the monoclinic space group P2₁/c. The molecules are arranged into chains by short C–H...O contacts along a two-fold screw axis. The quaternary 1-azidosulfonyl-2-ethyl-3-methylimidazolium tetrafluoroborate crystallized in Fdd2 with two independent ion pairs which engage in C–H...F interactions.

Keywords: azide; electrophilic azidation; imidazole; stability

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Cite This Article

MDPI and ACS Style

Laus, G.; Adamer, V.; Hummel, M.; Kahlenberg, V.; Wurst, K.; Nerdinger, S.; Schottenberger, H. Crystal Structure of 2-Ethylimidazole-1-sulfonyl Azide: A New Azidation Reagent. Crystals 2012, 2, 118-126.

AMA Style

Laus G, Adamer V, Hummel M, Kahlenberg V, Wurst K, Nerdinger S, Schottenberger H. Crystal Structure of 2-Ethylimidazole-1-sulfonyl Azide: A New Azidation Reagent. Crystals. 2012; 2(1):118-126.

Chicago/Turabian Style

Laus, Gerhard; Adamer, Verena; Hummel, Michael; Kahlenberg, Volker; Wurst, Klaus; Nerdinger, Sven; Schottenberger, Herwig. 2012. "Crystal Structure of 2-Ethylimidazole-1-sulfonyl Azide: A New Azidation Reagent." Crystals 2, no. 1: 118-126.

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