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Journals / Afyon Kocatepe Üniversitesi Fen ve Mühendislik Bilimleri Dergisi / 2022 / Cilt: 22 - Sayı: 1

Molecular Structure, Spectroscopic (IR, NMR, UV-VIS) Investigations and Non Linear Optical (NLO) Analysis of HDAC inhibitor 2-(N-(2- hydroxyphenyl)-2-propylpentanamide) with Quantum Chemical Calculations

HDAC inhibitörü 2-(N-(2-hidroksifenil)-2-propilpentanamid)' in Kuantum Kimyasal Hesaplamalar ile Moleküler Yapı, Spektroskopik (IR, NMR, UV-VIS) İncelemeleri ve Lineer Olmayan Optik (NLO) Analizi

Tuğba GÖCEN
Pages
1–15
Publication Date
2022-10-12
DOI
—
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AI Summary & Key Takeaways

AI Insight
⚡ TL;DR(Too Long; Didn't Read)

The structural parameters, vibrational wavenumbers, NMR chemical shifts of the molecule which are calculated theoretically are a good agreement with the experimental results obtained from the literature.

📌 3 Key Takeaways

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Objective & Hypothesis:2-(N-(2-hydroxyphenyl)-2-propylpentanamide) [OH-VPA], a histone deacetylase inhibitor (HDCA) with antitumor activity, is a new aryl valproic acid (VPA) derivative.
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Key Findings & Data:Optimized molecular geometry and harmonic vibrational frequencies of OH-VPA were calculated using the Density Functional Theory (DFT) B3LYP method with 6- 311++G(d,p) basis set.
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Conclusion & Impact:The structural parameters, vibrational wavenumbers, NMR chemical shifts of the molecule which are calculated theoretically are a good agreement with the experimental results obtained from the literature.
🔬Design:Modeling & Simulation
📍Scope:Comprehensive Sample
⚙️Variables:Domain Parameters

Abstract

2-(N-(2-hydroxyphenyl)-2-propylpentanamide) [OH-VPA], a histone deacetylase inhibitor (HDCA) with antitumor activity, is a new aryl valproic acid (VPA) derivative. In this work, structural, spectroscopic and electronic properties of OH-VPA were investigated by theoretical calculations. Optimized molecular geometry and harmonic vibrational frequencies of OH-VPA were calculated using the Density Functional Theory (DFT) B3LYP method with 6- 311++G(d,p) basis set. UV-Vis. electronic absorption parameters, HOMO-LUMO gap and molecular electrostatic potential (MEP) surface analyses and chemical reactivity descriptors of OH-VPA were performed to understand the reactivity of the molecule by the TD-DFT approach. Moreover, the values of the chemical shifts of the 13C NMR and 1H NMR were computed using the gauge independent atomic orbital (GIAO) method applying the same method and the same basis set as used in geometry optimization. The mean polarizability (α), the anisotropy of the polarizability (Δα) and the mean first-order hyperpolarizability (β) were calculated by using the finite field method. The high β values (2.144x10-30 esu) indicate that the studied compound may be a good candidate in the development of NLO materials. The structural parameters, vibrational wavenumbers, NMR chemical shifts of the molecule which are calculated theoretically are a good agreement with the experimental results obtained from the literature.

Özet

Antitümor aktiviteye sahip bir histon deasetilaz inhibitörü (HDCA) olan 2-(N-(2-hidroksifenil)-2-propilpentanamid) [OH-VPA], yeni bir aril valproik asit (VPA) türevidir. Bu çalışmada, OH-VPA’ nın yapısal, spektroskopik ve elektronik özellikleri teorik hesaplamalarla incelenmiştir. OH-VPA' nın optimize moleküler geometrisi ve harmonik titreşim frekansları, Yoğunluk Fonksiyonel Teorisi (DFT) B3LYP yöntemi kullanılarak 6-311++G(d,p) baz seti ile hesaplanmıştır. Molekülün reaktivitesini anlamak için UV-Vis elektronik absorpsiyon parametreleri, HOMO-LUMO enerji aralığı, moleküler elektrostatik potansiyel (MEP) yüzey analizleri ve kimyasal reaktivite tanımlayıcıları TD-DFT yaklaşımı ile gerçekleştirilmiştir. Ayrıca, OH-VPA’ nın 13C NMR ve 1H NMR' nin kimyasal kayma değerleri, geometri optimizasyonunda kullanılan aynı yöntem ve aynı temel set uygulanarak ayar içeren atomik orbital (GIAO) yöntemi kullanılarak hesaplanmıştır. Ortalama polarizebilite (α), polarizebilite anizotropisi (Δα) ve ortalama birinci mertebe hiperpolarizebilite (β) sonlu alan yöntemi kullanılarak hesaplanmıştır. Yüksek β değerleri (2,144x10-30 esu), incelenen bileşiğin NLO malzemelerinin geliştirilmesinde iyi bir aday olabileceğini göstermektedir. Molekülün teorik olarak hesaplanan yapısal parametreleri, titreşim dalga sayıları ve NMR kimyasal kaymaları literatürden elde edilen deneysel sonuçlarla iyi bir uyum içindedir.

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Cite This Article

GÖCEN, T. (2022). Molecular Structure, Spectroscopic (IR, NMR, UV-VIS) Investigations and Non Linear Optical (NLO) Analysis of HDAC inhibitor 2-(N-(2- hydroxyphenyl)-2-propylpentanamide) with Quantum Chemical Calculations. Afyon Kocatepe Üniversitesi Fen ve Mühendislik Bilimleri Dergisi, Cilt: 22 - Sayı: 1, 1–15. https://ajindex.com/articles/429577

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