Unusual_C2h-symmetric_trans-1-(bis-pyrrolidine)-tetra-malonate_h

A totally unanticipated regio- and stereoisomerically pure C2h-symmetric trans-1-(bis-pyrrolidine)-tetra-malonate hexa-adduct of C60 was obtained via a topologically controlled method, followed by a 1,3-dipolar cycloaddition reaction. The structures of the products were elucidated by 1H and 13C NMR and by X-ray crystallography. The unexpected regio- and stereoselectivity observed, supported by theoretical calculations, was found to be a consequence of malonate–pyrrolidine interactions.

CC-BY-4.0

The original dataset source can be reviewed here
Please use this identifier to cite or link to this collection:doi:10.19061/iochem-bd-2-18

This dataset derived results are published in:

Manuscript title: Unusual C2h-Symmetric trans-1-(Bis-pyrrolidine)-tetra-malonate Hexa-Adducts of C60: The Unexpected Regio- and Stereocontrol Mediated by Malonate–Pyrrolidine Interaction

Journal: Chem. Eur. J.

DOI: 10.1002/chem.201702866

PreviewTitleAuthor(s)ProgramCalculation typeMethod(s)Basis SetLinksEnergySolv.Vibr.Orb.
thumbnail.jpegMono-(Ester-pyrrolidine)_penta-adduct_of_C60Azmani, KhalidADF; 2016Geometry optimizationDFTTZP-42.12884089; Eh
thumbnail.jpeg_cis-anti-cis__pyridyl-substituted_bis-pyrrolidine_hexa-adducts_Azmani, KhalidADF; 2016Geometry optimizationDFTTZP-50.23202383; Eh
thumbnail.jpeg_cis-syn-cis__Pyridyl-substituted_bis-pyrrolidine_hexa-adducts_oAzmani, KhalidADF; 2016Geometry optimizationDFTTZP-50.23086059; Eh
thumbnail.jpeg_cis-anti-cis__Ester-substituted_bis-pyrrolidine_hexa-adducts_ofAzmani, KhalidADF; 2016Geometry optimizationDFTTZP-46.60354464; Eh
thumbnail.jpeg_cis-syn-cis__Ester-substituted_bis-pyrrolidine_hexa-adducts_of_Azmani, KhalidADF; 2016Geometry optimizationDFTTZP-46.60266884; Eh
thumbnail.jpegMono-(pyridyl-pyrrolidine)_penta-adduct_of_C60Azmani, KhalidADF; 2016Geometry optimizationDFTTZP-43.94516650; Eh
Collection's Items (Sorted by in order): 1 to 6 of 6
RSS Feed RSS Feed RSS Feed

Discover

Subject
Method
Basis
Program name
Calculation type