The Existence of a N→C Dative Bond in the C60 -Piperidine Complex

. 2021 Jan 25 ; 60 (4) : 1942-1950. [epub] 20201124

Status PubMed-not-MEDLINE Jazyk angličtina Země Německo Médium print-electronic

Typ dokumentu časopisecké články

Perzistentní odkaz   https://www.medvik.cz/link/pmid33022841

Grantová podpora
21773104 National Science Foundation of China
IGA_PrF_2020_022 Univerzita Palackého v Olomouci
19-27454X Grantová Agentura České Republiky
18-11851S Grantová Agentura České Republiky
No. CZ.02.1.01/0.0/0.0/16_019/0000754 ERDF-ESF "Nano 4 Future"

The complexes formed between carbon allotropes (C20 , C60 fullerenes, graphene, and single-wall carbon nanotubes) and piperidine have been investigated by means of computational quantum chemical and experimental IR and NMR techniques. Alongside hydrogen bonds, the C⋅⋅⋅N tetrel bond, and lone-pair⋅⋅⋅π interactions, the unexpected N→C dative/covalent bond has been detected solely in complexes of fullerenes with piperidine. Non-planarity and five-member rings of carbon allotropes represent the key structural prerequisites for the unique formation of a dative N→C bond. The results of thermodynamics calculations, molecular dynamics simulations, and NMR and FTIR spectroscopy explain the specific interactions between C60 and piperidine. The differences in behavior of individual carbon allotropes in terms of dative bonding formation brings a new insight into their controllable organic functionalization.

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