DNA Binding, DFT and Spectroscopic Studies of a Charge Transfer Complex Consisting of a Bioactive Donor 1-(2-Methylbenzy
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DNA Binding, DFT and Spectroscopic Studies of a Charge Transfer Complex Consisting of a Bioactive Donor 1‑(2‑Methylbenzyl)piperazine Gangadhari Suresh1 · Nampally Venkatesh1 · Baindla Naveen1 · Varukolu Mahipal1 · Madhavaram Madhavi1 · Tigulla Parthasarathy1 Received: 12 August 2019 / Accepted: 24 February 2020 © Springer Science+Business Media, LLC, part of Springer Nature 2020
Abstract A bioactive donor, 1-(2-methylbenzyl)piperazine is used to synthesize a new charge transfer complex (CTC) with the π-acceptor p-chloranil (p-CHL), which is characterized spectrophotometrically. The quantitative estimation of electronic interaction of the acceptor with the donor has been examined in acetonitrile (AN). The 1:1 composition of the CTC is confirmed by Jobs’ method of continuous variation and spectrophotometric (at 𝜆max 554 nm) methods at 298 K. The Benesi–Hildebrand method gives the formation constant (KCT) and molar extinction coefficient (ε) values of CTC. The spectral analysis was used to characterize CTC and its stability in solution and in the crystalline form. A DNA binding study of the CT-complex was carried out using UV–visible spectroscopy. A density functional theory (DFT) study of the CTC (gas phase/PCM) at using the B3LYP functional and 6-31G(d,p) basis set supports the experimental work. The optimization of the frontier molecular orbital surfaces was carried out by using the DFT-gasphase/PCM correlation methods. Mulliken atomic charges and reactive parameters of acceptor and donor recommend the MBPZ acts as a good electron donor and p-CHL acts as a good electron acceptor to form a highly stable electron transfer complex. Keywords 1-(2-Methylbenzyl)piperazine · p-Chloranil · Charge transfer · DFT study · DNA binding · Mulliken charges
1 Introduction The Lewis acid–base type charge transfer interactions of donor and acceptor molecules are associated with the formation of intensely colored complexes that absorb visible radiation in the corresponding region, as was first examined by Mulliken and Foster Electronic supplementary material The online version of this article (https://doi.org/10.1007/s1095 3-020-00989-x) contains supplementary material, which is available to authorized users. * Tigulla Parthasarathy [email protected] 1
Department of Chemistry, Osmania University, Hyderabad 500007, India
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[1, 2]. Charge transfer complexes play a major role in daily life due to their various potential applications in biological systems, such as DNA binding, anti-microbial and anti-bacterial activity as well as high efficiency non-linear optical materials, photocatalysis, and organic semi-conductors [3–7].
The acceptor p-CHL is a well-known quinine type 𝜋-electron acceptor used in chemical synthesis. It is generally used as a dye intermediate and agriculture fungicide. Potential symptoms from significant exposure include watery diarrhea, central nervous system depression and unconsciousness [8]. Technically, radical ion pairs are produced on the ac
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