NDLI: Methoxyindoles: stability and π-electron delocalization

Content Provider	Springer Nature Link
Author	Lopes Jesus, A. J. Redinha, J. S.
Copyright Year	2014
Abstract	Theoretical calculations performed on the methoxyindole isomers using the B3LYP, MP2, and MP4 methods combined with the 6-311++G(d,p) and 6-311++G(3df,3pd) basis sets reveal that the preferred conformation exhibited by all isomers has the exocyclic group co-planar to the ring plane. Moreover, certain positions of the substituent are found to be far more stable than others. In order to rationalize these results, the harmonic oscillator model of aromaticity (HOMA), together with the natural bond orbital (NBO) and natural resonance theories (NRT), have been employed to evaluate the π-electron delocalization in the different molecules. To act as a reference, the study has been extended to indole. The donor–acceptor interactions were energetically quantified by using the NBO deletion method. In general, the results given by the three approaches are in good agreement and provide complementary data about the main effects of the position/orientation of the methoxy group on the electronic structure of the indole ring. The electron redistribution resulting from the H/OCH$_{3}$ substitution was also analyzed in terms of the natural hybrid compositions of the π$_{CC}$ orbitals given by the NBO theory and atomic charges.
Starting Page	655
Ending Page	666
Page Count	12
File Format	PDF
ISSN	10400400
Journal	Structural Chemistry
Volume Number	26
Issue Number	3
e-ISSN	15729001
Language	English
Publisher	Springer US
Publisher Date	2014-10-14
Publisher Place	Boston
Access Restriction	One Nation One Subscription (ONOS)
Subject Keyword	Methoxyindoles π-electron delocalization Stability Natural bond orbital analysis Natural resonance theory Computer Applications in Chemistry Physical Chemistry Theoretical and Computational Chemistry
Content Type	Text
Resource Type	Article
Subject	Physical and Theoretical Chemistry Condensed Matter Physics

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