Abstract
1-(2-Fluoro-4-nitrophenyl)-4-(prop-2-yn-1-yl)piperazine was synthesized and single crystals were grown successfully by slow evaporation solution growth technique at room temperature. The compound was characterized by FTIR, 1H NMR and 13C NMR. From X-ray crystallography the crystal structure is monoclinic having a space group P21/c and the corresponding lattice parameters, a = 9.7366(8) Å, b = 17.9148(13) Å, c = 7.5270(6) Å and β = 102.397 (8)°. Packing studies of compound reveal the presence of several intermolecular interactions viz., C–H···O hydrogen bonding, C(aryl)–H···π interactions and stacking interactions of aromatic rings which stabilize the crystal lattice. The thermal stability of single crystal was determined by TG–DTA and DSC.
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Tagat JR, McCombie SW, Steensma RW, Lin SI, Nazareno DV, Baroudy B, Vantuno N, Xu S, Liu J (2001) Piperazine-based CCR5 antagonists as HIV-1 inhibitors. I: 2(S)-methyl piperazine as a key pharmacophore element. Bioorg Med Chem Lett 11:2143–2146
Wang H, Xiao J, Gao D, Zhang X, Yan H, Gong Z, Sun T, Li S (2011) Pharmacophore-based design, synthesis, and biological evaluation of novel chloro-pyridazine piperazines as human rhinovirus (HRV-3) inhibitors. Bioorg Med Chem Lett 21:1057–1059
Braccio MD, Grossi G, Roma G, Signorello MG, Leoncini G (2004) Synthesis and in vitro inhibitory activity on human platelet aggregation of novel properly substituted 4-(1-piperazinyl)coumarins. Eur J Med Chem 39:397–409
Tripathi RP, Tiwari VK, Bhattacharya SM, Tyagi K, Srivastava VML, Murthy PK (2003) 7-O-[4-methyl piperazine-1-(2-acetyl)]-2H-1-benzopyran-2-one: a novel antifilarial lead compound. Acta Tropica 87:215–224
Lyoqt RA, Titeler M, McKenney JD, Magee PS, Glennon RA (1986) Synthesis and evaluation of phenyl- and benzoylpiperazines as potential serotonergic agents. J Med Chem 29:630–634
Mattson RJ, Catt JD, Keavy D, Sloan CP, Epperson J, Gao Q, Hodges DB, Iben L, Mahle CD, Ryan E, Yocca FD (2003) Indanyl piperazines as melatonergic MT2 selective agents. Bioorg Med Chem Lett 13:1199–1202
Manoury PM, Dumas AP, Najer H (1979) Synthesis and analgesic activities of some (4-substituted phenyl-1-piperaziny1)alkyl 2-aminobenzoates and 2-aminonicotinates. J Med Chem 22:554–559
Jordan S, Koprivica V, Chen R, Tottori K, Kikuchi T, Altar CA (2002) The antipsychotic aripiprazole is a potent, partial agonist at the human 5-HT1A receptor. Eur J Pharm 441:137–140
Cusack B, Nelson A, Richelson E (1994) Binding of antidepressants to human brain receptors: focus generation compounds. Psychopharmacology 114:559–565
Cushion MT, Walzer PD, Ashbaugh A, Rebholz S, Brubaker R, Eynde JJV, Mayence A, Huang TL (2006) In vitro selection and in vivo efficacy of piperazine- and alkanediamide-linked bisbenzamidines against Pneumocystis pneumonia in mice. Antimicrob Agents Chemother 50:2337–2343
Satake N, Shibata S, Suh TK, Flores F (1984) An alpha-adrenoceptor-blocking action of SGB-483, a new piperazine antihypertensive agent in isolated vascular smooth muscles. Blood Vessels 21:298–305
Goldman L, Williams JH (1954) Derivatives of 1-piperazinecarboxylic acid as sedatives. J Am Chem Soc 76:6078–6080
Dixit SK, Mishra N, Sharma M, Singh S, Agarwal A, Awasthi SK, Bhasin VK (2012) Synthesis and in vitro antiplasmodial activities of fluoroquinolone analogues. Eur J Med Chem 51:52–59
Neupane CS, Awasthi SK (2012) Unique trifurcated hydrogen bonding in a pseudopolymorph of tricyclohexane triperoxide (TCTP) and its thermal studies. Tetrahedron Lett 53:6067–6070
Yadav N, Dixit SK, Bhattacharya A, Mishra LC, Sharma M, Awasthi SK, Bhasin VK (2012) Antimalarial activity of newly synthesized chalcone derivatives in vitro. Chem Boil Drug Des 80:340–347
Singh S, Singh MK, Agarwal A, Awasthi SK (2011) 2-(4-Chlorophenyl)chromen-4-one. Acta Crystallogr Sect E 67(Pt 12):o3163. doi:10.1107/S1600536811043832
Khalaj A, Nakhjiri M, Negahbani AS, Samadizadeh M, Firoozpour L, Rajabalian S, Samadi N, Faramarzi MA, Adibpour N, Shafiee A, Foroumadi A (2011) Discovery of a novel nitroimidazolyleoxazolidinone hybrid with potent anti Gram-positive activity: synthesis and antibacterial evaluation. Eur J Med Chem 46:65–70
Padmanabhan K, Venkatesan K, Ramamurthy V (1987) Structure-reactivity correlation of photochemical reactions in organic crystals: intramolecular hydrogen abstraction in an aromatic nitro compound. J Chem Soc Perkin Trans II:1153–1158
Viswamitra MA, Bandekar RJ Jr, Desiraju GR (1993) Evidence for O–H C and N–H C hydrogen bonding in crystalline alkynes, alkenes, and aromatics. J Am Chem Soc 115:4868–4869
Thakur TS, Sathishkumar R, Dikundwar AG, Row TNG, Desiraju GR (2010) Third polymorph of phenylacetylene. Cryst Growth Des 10:4246–4249
Gło′wka ML, Martynowski D, Kozàowska K (1999) Stacking of six-membered aromatic rings in crystals. J Mol Struct 474:81–89
Acknowledgments
Satish Kumar Awasthi is thankful to University of Delhi for financial assistance and University Scientific Instrumentation Center (USIC), University of Delhi, Delhi 110007, Delhi India for analytical data. Chiranjeev Sharma is thankful to UGC for providing SRF. Gunjan Pandey is thankful, to UGC for providing JRF.
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Awasthi, S.K., Sharma, C., Yadav, M. et al. Thermal and Crystallographic Studies of 1-(2-Fluoro-4-Nitrophenyl)-4-(Prop-2-yn-1-yl)Piperazine Single Crystal. Proc. Natl. Acad. Sci., India, Sect. A Phys. Sci. 84, 19–25 (2014). https://doi.org/10.1007/s40010-013-0102-8
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DOI: https://doi.org/10.1007/s40010-013-0102-8