(Z)-Etil 4-kloro-2-[2-(2-metiloksifenil)hidrazon]-3-okso-butanoat Kristalinin Hesaplamalı Kimya Yöntemiyle Lokal ve Global Kimyasal Aktivite Hesaplamaları ve DNA Bazları ile Yük Transferinin Tayini

Year 2019, , 93 - 108, 18.12.2019

Zeynep Demircioğlu , Cem Cüneyt Ersanlı , Gökhan Alpaslan

https://doi.org/10.33484/sinopfbd.562618

Cited By: 2

Abstract

(Z)-Etil 4-kloro-2-[2-(2-metiloksifenil)hidrazon]-3-okso-butanoat
kristalinin Hirshfeld
yüzey analizi ile moleküler etkileşimleri, Hirshfeld yüzey haritaları (d_norm,
d_i, d_e), 2-boyutlu parmak izi ve atomların birbiriyle
etkileşim %’si incelenmiştir. Moleküler yapıya ait tüm kuramsal hesaplamalar
Gaussian09 programı kullanılarak B3LYP yoğunluk fonksiyoneli ve 6-311G(d,p) baz seti ile hesaplanmıştır. Bu çalışmanın amacı
lokal ve global kimyasal aktivite parametrelerini inceleyerek yapının
elektrofilik ve nükleofilik doğasını anlamaktır. Bu kapsamda moleküler
elektrostatik potansiyel (MEP), Fukui fonksiyonlar, net yükler (MPA ve NPA)
hesaplanmıştır. Bunlara ilave olarak ECT (elektrofilik-bazlı yük transferi)
yöntemi ile DNA bazları ve çalışılan moleküle ait yük geçişleri ΔN yük
transfer parametresi hesaplanarak yük geçişleri ve elektrofilik ve nükleofilik
doğa belirlenmiştir. Bunlara ilave olarak, çalışılan yapının ikinci dereceden
lineer olmayan optik (NLO) özellikleri kutuplanabilirlik parametreleri ile
hesaplanmıştır ve optik bir materyal olma eğilimi incelenmiştir. 

Keywords

YFK, elektrofilik&nükleofilik doğa, DNA/ECT, Hirshfeld yüzey analizi

Supporting Institution

Sinop Üniversitesi

Project Number

FEF-1901-18-27

Thanks

Bu çalışma Sinop Üniversitesi Bilimsel Araştırma Projeleri Koordinasyon birimince desteklenmiştir. Proje Numarası: FEF-1901-18-27, 2018.

Calculations of Charge Transfer with DNA bases and Local&Global Chemical Activity by Computational Chemistry Method of (Z)-Ethyl 4-chloro-2-[2-(2-methoxyphenyl)hydrazono]-3-oxobutanoate Crystal

Abstract

The intermolecular interactions of the (Z)-Ethyl 4-chloro-2-[2-(2-methoxyphenyl)hydrazono]-3-oxobutanoate crystal with Hirshfeld surface analysis, Hirshfeld surface maps (d_norm, d_i, d_e), 2-d fingerprint plots (FPs is used for identifiying the nature of intermolecular interactions, ) and the percentage of interactions of atoms with each other were investigated . All theoretical calculations of molecular structure were calculated by Gaussian09 program with B3LYP density functional model with 6-311G(d,p) basis set. The aim of this paper is to determine the electrophilic and nucleophilic nature of studied compound by examining the local and global chemical activity parameters. In this context, molecular electrostatic potential (MEP), Fukui functions, net loads (MPA and NPA) were calculated. In addition, ECT (electrophilicity-basedcharge transfer) method examines the electrophilic and nucleophilic nature of the molecule and DNA bases, taking into account their interactions with ΔN (charge transfer) parameter. Also, nonlinear optical properties (NLO) were determined by polarizability parameters and tendency to be an optical material was investigated.

Keywords

DFT, electrophilic and nucleophilic nature, DNA/ECT, Hirshfeld surface analysis

Project Number

FEF-1901-18-27

References

• [1] Su X, Aprahamian I, 2014. Hydrazone-based Switches, Metallo-Assemblies and Sensors Chemical Society Reviews, 43: 1963-1981.
• [2] Gaikward ND, Patil SV, Bobade VD, 2012. Synthesis and biological evaluation of some novel thiazole substituted benzotriazole derivatives Bioorg. Med. Chem. Let., 22: 3449-3454.
• [3] Kaplancikli ZA, Yurtta L, Turan-Zitouni G, Ozdemir A, Goger G, Demirci F, Mohsend UA, 2014. Synthesis and antimicrobial activity of new pyrimidine-hydrazones Lett. Drug Des. Discov., 11 (1): 76-81.
• [4] Alpaslan G, Özdamar Ö, Odabaşoğlu M, Ersanlı CC, Erdönmez A, 2006. (Z)-Ethyl 4-chloro-2-[2-(2-methoxyphenyl)hydrazono]-3oxobutanoate Acta Cryst. E62: o1828-o1830.
• [5] Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Scalmani G, Barone V, Mennucci B, Petersson GA, Nakatsuji H, Caricato M, Li X, Hratchian HP, Izmaylov AF, Bloino J, Zheng G, Sonnenberg JL, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M, Nakajima T, Honda Y, Kitao O, Nakai H, Vreven T, Montgomery JA, Peralta Jr., JE, Ogliaro F, Bearpark M, Heyd JJ, Brothers E, Kudin KN, Staroverov VN, Kobayashi R, Normand J, Raghavachari K, Rendell A, Burant JC, Iyengar SS, Tomasi J, Cossi M, Rega N, Millam JM, Klene M, Knox JE, Cross JB, Bakken V, Adamo C, Jaramillo J, Gomperts R, Stratmann RE, Yazyev O, Austin AJ, Cammi R, Pomelli C, Ochterski JW, Martin RL, Morokuma K, Zakrzewski VG, Voth GA, Salvador P, Dannenberg JJ, Dapprich S, Daniels AD, Farkas O, Foresman JB, Ortiz JV, Cioslowski J, Fox DJ, 2009. Gaussian 09, Revision E.01, Gaussian, Inc., Wallingford CT.
• [6] Wolff DJGSK, McKinnon JJ, Turner MJ, Jayatilaka D, Spackman MA, 2012. Crystal Explorer, Version3.1.
• [7] Samanta T, Deyv L, Dinda J, Chattopadhyay SK, Seth, SK, 2014. Structural characterization and Hirshfeld surface analysis of a CoIIcomplex with imidazo[1,2-a] pyridine J. Mol. Struct., 1068: 58-70.
• [8] Bahgat K, Fraihat S, 2015. Normal coordinate analysis, molecular structure, vibrational, electronic spectra and NMR investigation of 4-amino-3-phenyl-1H-1,2,4-triazole-5(4H)-thione by ab initio HF and DFT method, Spectrochim. Acta A, 135: 1145-1155.
• [9] Haress NG, El-Emam A, Al-Deab OA, Panicker CY, Al-Saadi A, Van Alsenols C, Ahmad War J, 2015. Vibrational spectroscopic and molecular dockings tudy of 2-benzylsulfanyl-4-[(4-methylphenyl)-sulfanyl]-6-pentylpyrimidine-5carbonitrile, a potential chemo the rapeutic agent Spectrochem. Acta A, 137: 569-580, 2015.
• [10] Mulliken RS, 1955. Electronic population analysis on LCAO-MO molecular wave functions. I. J. Chem. Phys., 23(10): 1833-1840.
• [11] Bahgat K, Fraihat S, 2015. Normal coordinate analysis, molecularstructure, vibrational, electronic spectra and NMR investigation of 4-amino-3-phenyl-1H-1,2,4-triazole-5(4H)-thione by ab initio HF and DFT method Spectrochim. Acta A, 135: 1145-1155.
• [12] Volkov A, Gatti C, Abramov Y, Coppens P, 2000. On the origin of topological differences between experimental and theoretical crystal charge densities Acta Cryst., A56: 252-258.
• [13] Mulliken RSJ, 1955. Electronic Population Analysis on LCAO–MO Molecular Wave Functions Chem. Phys., 23: 1833-1840.
• [14] Yang W, Parr RG, 1985. Hardness, softness, and the fukui function in the electronic theory of metals and catalysis Proc. Natl. Acad. Sci., 82: 6723-6726.
• [15] Çınarlı M, Yüksektepe Ataol Ç, Taş M, Bati H, 2018. Synthesis, crystal structure, Hirshfeld surface and DFT studies of([Cu(3-ptp)2(p-TS)2]) from decomposition of tosyl hydrazone J. Mol. Struct., 1169: 59-67.
• [16] Basshard C, Suttur K, Pretre P, Flörsheimer M, Kaatz P, Günter P, 1995. Organic nonlinear optical materials. 5th ed. John Wiley&Sons, Switzerland.
• [17] Nalwa HS, Miyata S, 1997. Nonlinear optics of organic molecules and polymers. CRC Press, 896, New York.
• [18] Alyar H, Kantarci Z, Bahat M, Kasap E, 2007. Investigation of torsional barriers and nonlinear optical (NLO) properties of phenyltriazines J. Mol. Struct., 834: 516-520.