INVESTIGATION OF STRUCTURAL AND REACTIVITY PROPERTIES OF SOME HALOGENATED PIPERAZINES

Year 2024, Volume: 12 Issue: 1, 1 - 6, 27.02.2024

Fulden Demircioğlu Ovezov Cemal Parlak Özgür Alver

https://doi.org/10.20290/estubtdb.1315254

Abstract

The chemical and biological activities are strongly related to the molecular structures and the media to which the molecules were subjected. Therefore, it is crucial to know the behaviors of molecular systems in the examined solvent media and their structural and reactivity properties. In the framework of this study, molecular and reactivity properties of some halogenated piperazine derivatives were undertaken by using the density functional theory. It was observed that halogen atoms have considerable effects on the behavior of piperazine molecule. Further, the atypical characteristic of fluorine affecting conformational preference is observed for di-halogenated piperazines with the same halogen atoms.

Keywords

DFT, Halogen effect, Molecular structure, Reactivity properties

HALOJEN KATKILI BAZI PİPERAZİN TÜREVLERİNİN YAPISAL VE REAKTİF ÖZELLİKLERİNİN İNCELENMESİ

Abstract

Kimyasal ve biyolojik aktiviteler, moleküler yapılarla ve moleküllerin tabi tutulduğu ortamla güçlü bir şekilde ilişkilidir. Bu nedenle, çözücü ortamdaki moleküler sistemlerin davranışlarını ve bunların yapısal ve reaktivite özelliklerini bilmek oldukça önemlidir. Bu çalışma çerçevesinde, bazı halojenli piperazin türevlerinin moleküler ve reaktivite özellikleri, yoğunluk fonksiyonel teorisi kullanılarak ele alınmıştır. Halojen atomlarının piperazin moleküllerinin davranışları üzerinde önemli etkileri olduğu gözlemlenmiştir. Ayrıca, konformasyonel tercihi etkileyen florin atipik özelliği, aynı halojen atomlarına sahip di-halojenli piperazinler için de gözlemlenmektedir.

Keywords

DFT, Halojen etkisi, Moleküler yapı, Reaktivite özellikleri

References

• [1] Resmi KS, Mary YS, Varghese HT, Panicker CY, Pakosinska-Parys M, Alsenoy CV, J Mol Struct 2015; 1098: 130–145.
• [2] Hosna S, Janzen DE, Mary YS, Resmi KS, Thomas R, Mohamed R, Wajda S. Molecular structure, spectroscopic, dielectric and thermal study, nonlinear optical properties, natural bond orbital, HOMO-LUMO and molecular docking analysis of (C6Cl2O4) (C10H14N2F)2·2H2O. Spectrochim Acta A 2018; 204: 328–339.
• [3] Pang W, Lv J, Du S, Wang J, Wang J, Zeng Y. Preparation of curcumin-piperazine coamorphous phase and fluorescence spectroscopic and density functional theory simulation studies on the interaction with bovine serum albumin. Mol Pharmaceutics 2017; 14: 3013−3024.
• [4] Lipin R, Dhanabalan AK, Gunasekaran K, Solomon RV. Piperazine-substituted derivatives of favipiravir for Nipah virus inhibition: What do in silico studies unravel? SN Appl Sci 2021; 3: 110.
• [5] Satoskar RS, Kala, Bhandarkar SD. Pharmacology and Pharmacotherapeutics. 3nd ed. Bombay Popular Prakashan Pvt Ltd, Bombay: 1976.
• [6] Parlak C, Alver Ö, Bağlayan Ö. Quantum mechanical simulation of molnupiravir drug interaction with Si-doped C60 fullerene. Comput Theor Chem 2021; 1202: 113336.
• [7] Bağlayan Ö, Parlak C, Dikmen G, Alver Ö. The quest of the most stable structure of a carboxyfullerene and its drug delivery limits: A DFT and QTAIM approach. Comput Theor Chem 2023; 1221: 114036.
• [8] Omurtag Özgen PS, Durmaz H, Parlak C, Alver Ö, Bağlayan Ö. Non-covalent functionalization of single walled carbon nanotubes with pyrene pendant polyester: A DFT supported study. J Mol Struct 2020; 1209: 127943.
• [9] Hohenberg P, Kohn W. Inhomogeneous electron gas. Phys Rev B 1964; 136: 864–871.
• [10] Alver Ö, Parlak C. Vibrational spectroscopic investigation and conformational analysis of 1-cyclohexylpiperazine. J Mol Struct 2010; 975: 85-92.
• [11] Bağlayan Ö, Keşan G, Parlak C, Alver Ö, Şenyel M, Vibrational investigation of 1-cyclopentylpiperazine: A combined experimental and theoretical study. Sci China Phys Mech 2014; 57: 1654-1661.
• [12] Keşan G, Bağlayan Ö, Parlak C, Alver Ö, Şenyel M. FT-IR and Raman spectroscopic and quantum chemical investigations of some metal halide complexes of 1-phenylpiperazine. Spectrochim Acta A 2012; 88: 144-155.
• [13] Tomasi J, Mennucci B, Cammi R. Quantum mechanical continuum solvation models. Chem Rev 2005; 105: 2999–3094.
• [14] Frisch MJ, Trucks GW, Schlegel HB, et al. Gaussian 16. Revision C.01. Gaussian Inc. Wallingford, CT, USA: 2016.
• [15] Dennington RD, Keith TA, Millam JM. GaussView 6.0.16. Gaussian Inc. Wallingford, CT, USA: 2016.
• [16] SenGupta S, Maiti N, Chadha R, Kapoor S. Probing of different conformations of piperazine using Raman spectroscopy. Chem Phys 2014; 436–437: 55–62.
• [17] Fukui K. Role of frontier orbitals in chemical reactions. Science 1982; 218: 747–754.
• [18] Ayala PY, Scuseria GE. Linear scaling second-order Moller–Plesset theory in the atomic orbital basis for large molecular systems. J Chem Phys 1999; 110: 3660–3671.
• [19] Hoffmann R, Schleyer vR, Schaefer HF. Predicting molecules-more realism, please! Angew Chem Int 2008; 47: 7164–7167.