Theoretical study of the effects of substituents (F, Cl, Br, CH3, and CN) on the aromaticity of borazine

This paper presents a theoretical study of the effects of substituents (F, Cl, Br, CH 3 , and CN) on the aromaticity of borazine (B 3 N 3 H 6 ), using density functional theory (DFT) and the Hartree-Fock (HF) method. The calculations to optimize the geometries, structural properties, and vibrational...

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Bibliographic Details
Published in:Journal of molecular modeling 2018-01, Vol.24 (1), p.34-11, Article 34
Main Authors: Costa, Alexandre, Costa, Elizama Ramos, Silva, Adilson Luís Pereira, Tanaka, Auro Atsushi, de Jesus Gomes, Jaldyr
Format: Article
Language:English
Subjects:
Aromaticity
Characterization and Evaluation of Materials
Chemistry
Chemistry and Materials Science
Computer Appl. in Life Sciences
Computer Applications in Chemistry
Density functional theory
Energy gap
Hydrogen atoms
Molecular Medicine
Molecular orbitals
Original Paper
Theoretical and Computational Chemistry
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Summary:This paper presents a theoretical study of the effects of substituents (F, Cl, Br, CH 3 , and CN) on the aromaticity of borazine (B 3 N 3 H 6 ), using density functional theory (DFT) and the Hartree-Fock (HF) method. The calculations to optimize the geometries, structural properties, and vibrational frequencies were performed using the same 6–311G(d,p) and 6–311++G(d,p) basis sets, comparing the methods with experimental results. In the analysis of the NICS ZZ values, it was found that that replacing the hydrogen atoms by halogen atoms (F, Cl, and Br) and CH 3 reduced the aromaticity of the borazine molecule, while use of the CN group resulted in NICS ZZ values (0.9–2.0 Å) very close to those of borazine, presenting the following order of increasing aromaticity: B 3 N 3 H 3 -(Br) 3  
ISSN:1610-2940
0948-5023
DOI:10.1007/s00894-017-3555-x