The influence of heteroatoms on the aromatic character and the current pathways of B2N2-dibenzo[a,e]pentalenes

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Dimitrova , M , Fliegl , H & Sundholm , D 2017 , ' The influence of heteroatoms on the aromatic character and the current pathways of B2N2-dibenzo[a,e]pentalenes ' , Physical Chemistry Chemical Physics , vol. 19 , no. 30 , pp. 20213-20223 . https://doi.org/10.1039/C7CP02964K

Title: The influence of heteroatoms on the aromatic character and the current pathways of B2N2-dibenzo[a,e]pentalenes
Author: Dimitrova, Maria; Fliegl, Heike; Sundholm, Dage
Contributor organization: Department of Chemistry
Laboratory for Instruction in Swedish (-2016)
Date: 2017-08-14
Language: eng
Number of pages: 11
Belongs to series: Physical Chemistry Chemical Physics
ISSN: 1463-9076
DOI: https://doi.org/10.1039/C7CP02964K
URI: http://hdl.handle.net/10138/309505
Abstract: Four polycyclic molecules have been investigated at the DFT B3LYP/def2-TZVP level of theory using calculated magnetically induced current densities as an indicator of their (anti)aromaticity. Complicated current pathways were found in dibenzo[a,e]pentalene and its three heterocyclic analogues each containing two boron and two nitrogen atoms. The antiaromatic character of the pentalene moiety is weaker in the hydrocarbon molecule and in 5,11-dihydrobenzo[d]benzo[4,5][1,2,3]azadiborolo[3,2-b][1,2,3]azadiborole as compared to the pentalene molecule. The antiaromatic character of the pentalene moiety is completely absent in the other two heterocyclic structures. In 6,12-dihydrobenzo[d]benzo[4,5][1,2,3]diazaborolo[2,1-a][1,2,3]diazaborole all four molecular rings are aromatic according to the ring-current criterion, and in 6,12-dihydrobenzo[d]benzo[3,4][1,2,5]azadiborolo[1,2-a][1,3,2]diazaborole, the diazaborole ring is aromatic, while the azadiborole ring is antiaromatic. In all four molecules the six-membered rings are aromatic sustaining a weaker ring current than benzene does.
Subject: INDEPENDENT CHEMICAL-SHIFTS
POLYCYCLIC CONJUGATED HYDROCARBONS
ZETA VALENCE QUALITY
GAUSSIAN-BASIS SETS
RING-CURRENT MODEL
CURRENT-DENSITY
ANTIAROMATIC CHARACTER
ATOMS LI
MOLECULES
NICS
116 Chemical sciences
114 Physical sciences
Peer reviewed: Yes
Rights: unspecified
Usage restriction: openAccess
Self-archived version: acceptedVersion


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