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Synthesis and Structural Characterization of 1-[2-(5-Nitro-1H-indol-2-yl)phenyl]methylpyridinium Chloride
School of Chemistry, University of Wollongong, Wollongong, NSW 2522, Australia
Department of Chemistry, Srinakharinwirot University, Bangkok 10110, Thailand
School of Biomedical, Biomolecular and Chemical Sciences, Chemistry M313, The University of Western Australia, Crawley, W.A. 6009, Australia
* Author to whom correspondence should be addressed.
Received: 29 July 2011; in revised form: 22 August 2011 / Accepted: 25 August 2011 / Published: 6 September 2011
Abstract: In the course of studies on hybrid antibacterials incorporating 2-aryl-5-nitro-1H-indole moieties as potential bacterial NorA efflux pump inhibitors, the compound 1-[2-(5-nitro-1H-indol-2-yl)phenyl]methylpyridinium chloride (2) was synthesized and structurally characterized. This pyridinium chloride salt crystallized in the monoclinic space group P21/c with the following unit cell dimensions: a 10.274(3) Å, b 13.101(4) Å, c 13.439(4) Å, b 107.702(7)°, V 1723.2(9) Å3, Z (f.u.) = 4; R1 = 0.048, and wR2 = 0.13. Of interest in the single crystal X-ray structure is the (intramolecular) disposition of the pyridinium plane over the indole heterocyclic residue [interplanar dihedral angle 17.91(4)°].
Keywords: indole; pyridinium salt; X-ray crystal structure
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Bremner, J.B.; Samosorn, S.; Skelton, B.W.; White, A.H. Synthesis and Structural Characterization of 1-[2-(5-Nitro-1H-indol-2-yl)phenyl]methylpyridinium Chloride. Molecules 2011, 16, 7627-7633.
Bremner JB, Samosorn S, Skelton BW, White AH. Synthesis and Structural Characterization of 1-[2-(5-Nitro-1H-indol-2-yl)phenyl]methylpyridinium Chloride. Molecules. 2011; 16(9):7627-7633.
Bremner, John B.; Samosorn, Siritron; Skelton, Brian W.; White, Allan H. 2011. "Synthesis and Structural Characterization of 1-[2-(5-Nitro-1H-indol-2-yl)phenyl]methylpyridinium Chloride." Molecules 16, no. 9: 7627-7633.