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

Yıl 2017, Cilt: 38 Ek Sayı 4, 138 - 155, 08.12.2017

Mustafa Elik Goncagül Serdaroğlu

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

Cited By: 17

Öz

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.

Anahtar Kelimeler

Quantum chemical descriptors, substituent effect, NBO

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^-1 olarak bulunmuştur.

Anahtar Kelimeler

Kuantum kimyasal tanımlayıcılar, bağlı grup etkisi, NBO, FMO analizi

Kaynakça

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