Dataset Information

Regioselective Nitration of Halogenated Benzo[c]cinnolines and Benzenoids.

ABSTRACT: Electrophilic nitration of halo-substituted benzo[c]cinnolines and benzenoids has been achieved regioselectively. The nitro group entry was always ortho to the halo group or/and the aromatic ring. This regioselective electrophilic ortho-nitration was accomplished in mixed acid/mild temperature conditions. Regioselectivity ortho to the halo/ring group(s) was observed with or without proximal steric hindrance. Chlorides and bromides worked equally well in directing these high-yielding ortho-selective reactions.

SUBMITTER: Epps AK

PROVIDER: S-EPMC4880372 | biostudies-literature | 2015 Aug

REPOSITORIES: biostudies-literature

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Regioselective Nitration of Halogenated Benzo[c]cinnolines and Benzenoids.

Epps Ayunna K AK Horne Tonya M TM Jackson ShaNese S Sands Bridgette B Mandouma Ghislain G

International journal for innovation education and research 20150801 8

Electrophilic nitration of halo-substituted benzo[c]cinnolines and benzenoids has been achieved regioselectively. The nitro group entry was always ortho to the halo group or/and the aromatic ring. This regioselective electrophilic ortho-nitration was accomplished in mixed acid/mild temperature conditions. Regioselectivity ortho to the halo/ring group(s) was observed with or without proximal steric hindrance. Chlorides and bromides worked equally well in directing these high-yielding ortho-select ...[more]

PMID: 27239565

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Project description:In order to explore atomic asymmetry and molecular chirality in 2D space, benzenoids composed of 3 to 11 hexagons in 2D space were enumerated in our laboratory. These benzenoids are regarded as planar connected polyhexes and have no internal holes; that is, their internal regions are filled with hexagons. The produced dataset was composed of 357,968 benzenoids, including more than 14 million atoms. Rather than simply labeling the huge number of atoms as being either symmetric or asymmetric, this investigation aims at exploring a quantitative graph theoretical descriptor of atomic asymmetry. Based on the particular characteristics in the 2D plane, we suggested the weighted atomic sum as the descriptor of atomic asymmetry. This descriptor is measured by circulating around the molecule going in opposite directions. The investigation demonstrates that the weighted atomic sums are superior to the previously reported quantitative descriptor, atomic sums. The investigation of quantitative descriptors also reveals that the most asymmetric atom is in a structure with a spiral ring with the convex shape going in clockwise direction and concave shape going in anticlockwise direction from the atom. Based on weighted atomic sums, a weighted F index is introduced to quantitatively represent molecular chirality in the plane, rather than merely regarding benzenoids as being either chiral or achiral. By validating with enumerated benzenoids, the results indicate that the weighted F indexes were in accordance with their chiral classification (achiral or chiral) over the whole benzenoids dataset. Furthermore, weighted F indexes were superior to previously available descriptors. Benzenoids possess a variety of shapes and can be extended to practically represent any shape in 2D space-our proposed descriptor has thus the potential to be a general method to represent 2D molecular chirality based on the difference between clockwise and anticlockwise sums around a molecule.

Dataset Information

Regioselective Nitration of Halogenated Benzo[c]cinnolines and Benzenoids.

Publications

Regioselective Nitration of Halogenated Benzo[c]cinnolines and Benzenoids.

Similar Datasets

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