A Computational Study of 1-Substituted Methyl 9-Methyl-9H-Pyrido[3,4- b]indole-3-Carboxylate: Quantum Chemical Descriptors, FMO and NBO Analysis

Mustafa Elik; Goncagül Serdaroğlu

doi:10.17776/csj.356185

EN TR

A Computational Study of 1-Substituted Methyl 9-Methyl-9H-Pyrido[3,4- b]indole-3-Carboxylate: Quantum Chemical Descriptors, FMO and NBO Analysis

Abstract

This work dealt with the investigation of the methyl 9H-pyrido[3,4-b]indole-3-carboxylate (Basic compound) and its C1-substituted derivatives to search for the best substituent group that enhances the chemical reactivity behavior of the Basic compound. In this context, DFT (Density Functional Theory) calculations were performed at B3LYP level of theory at three basis sets, also in 10 different solvents because the chemical behavior strongly depends on the solvent media. This study revealed that the anthracene-9-yl substitution on the C1-position of the Basic compound has increased the chemical reactivity of the Basic compound more than those of the other substituent groups. Also, the results were supported by the NBO analysis: the highest electron delocalization for the structure A was found out π C19-C20→ p_v C42-C43 with the interaction energy of the 50.98 kcalmol-1, due to the anthracene-9-yl substitution on the C1-position of the Basic compound makes the electron delocalization on the substituted compound enhances, at 6-311++g**basis set in the water phase.

Keywords

1- Sübstitüeli Metal-9-Metil-9H-Pirido [3,4-b]indol-3-Karboksilat Üzerine Hesaplamalı Kimya Çalışması: Kuantum Kimyasal Belirleyiciler, FMO ve NBO Analizi

Öz

Bu çalışma metil 9H-pirido [3,4-b] indol-3-karboksilat (Temel bileşik) ve bu bileşiğin C1-substitüeli türevlerinin incelenmesi ile Temel bileşiğin kimyasal tepkime davranışını arttıran en iyi substitüe grubu belirlemek ile ilgilenmiştir. Bu bağlamda DFT (Yoğunluk Fonksiyonel Teori) hesaplamaları 3 temel set ve kimyasal aktivite davranışı çözücü ortamına bağlı olduğundan dolayı 10 farklı çözücü ortamında yapılmıştır. Bu çalışma, Temel bileşiğin C1-konumundaki antrasen-9-il substitüe grubunun, diğer sübstitüe gruplarınınkinden daha fazla Temel bileşiğin kimyasal reaktivitesini arttırdığını ortaya koymuştur. Ayrıca, sonuçlar NBO analizi ile desteklenmiştir: 6-311++g(d,p) temel seti ile su fazında, Temel bileşiğin C1 konumunda antrasen-9-il substitüe grubu bulunduğunda elektron delokalizasyonu arttığından dolayı, A bileşiğinin en büyük elektron delokalizasyonu π C19-C20→ p_v C42-C43 elektronik geçişi için 50.98 kcalmol^-1olarak bulunmuştur.

Anahtar Kelimeler

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Details

Primary Language

English

Subjects

Pharmacology and Pharmaceutical Sciences

Journal Section

Research Article

Authors

Mustafa Elik
Cumhuriyet University, Education Faculty
Türkiye

Goncagül Serdaroğlu
Cumhuriyet University, Education Faculty

Publication Date

December 8, 2017

Submission Date

November 19, 2017

Acceptance Date

December 6, 2017

Published in Issue

Year 2017 Volume: 38 Number: 4

DOI

https://doi.org/10.17776/csj.356185

IZ

https://izlik.org/JA92SN77TW

Cite

RIS / Bibtex

APA

Elik, M., & Serdaroğlu, G. (2017). A Computational Study of 1-Substituted Methyl 9-Methyl-9H-Pyrido[3,4- b]indole-3-Carboxylate: Quantum Chemical Descriptors, FMO and NBO Analysis. Cumhuriyet Science Journal, 38(4), 138-155. https://doi.org/10.17776/csj.356185