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Issue 9, 2014
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Experimental and theoretical analysis of lp⋯π intermolecular interactions in derivatives of 1,2,4-triazoles

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Abstract

In the present study, we have synthesized and characterized two biologically active 1,2,4-triazole derivatives, a fluoro derivative, namely (E)-3-(4-fluoro-3-phenoxyphenyl)-4-((4-fluorobenzylidene)amino)-1-(morpholinomethyl)-1H-1,2,4-triazole-5(4H)-thione (TRZ-1), and a chloro derivative, namely (E)-4-((4-chlorobenzylidene)amino)-3-(4-fluoro-3-phenoxyphenyl)-1-(morpholinomethyl)-1H-1,2,4-triazole-5(4H)-thione (TRZ-2), via single crystal and powder X-ray diffraction. The chloro derivative crystallizes in an anhydrous form (TRZ-2A) and a solvated one (TRZ-2B) due to the presence of a toluene molecule in the crystal. This solvatomorphic behavior has been studied in detail using different thermal techniques, namely DSC and TGA, combined with hot stage microscopy (HSM). All of the three crystal structures show the presence of different intermolecular interactions of the type C–H⋯O, C–H⋯S[double bond, length as m-dash]C, C–H⋯π, C–H⋯X (X = –F, –Cl), π⋯π and lp⋯π interactions. The fingerprints for all these interactions were evaluated using Hirshfeld surfaces. The nature and energetics associated with these interactions were characterized using PIXEL and supported by ab initio quantum mechanical calculations using TURBOMOLE. In addition, the calculations performed on the evaluation of the electrostatic potential provide deeper insights into the nature of lp⋯π interactions.

Graphical abstract: Experimental and theoretical analysis of lp⋯π intermolecular interactions in derivatives of 1,2,4-triazoles

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The article was received on 08 Nov 2013, accepted on 03 Dec 2013 and first published on 05 Dec 2013


Article type: Paper
DOI: 10.1039/C3CE42286K
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Citation: CrystEngComm, 2014,16, 1702-1713
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    Experimental and theoretical analysis of lp⋯π intermolecular interactions in derivatives of 1,2,4-triazoles

    R. Shukla, T. P. Mohan, B. Vishalakshi and D. Chopra, CrystEngComm, 2014, 16, 1702
    DOI: 10.1039/C3CE42286K

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