Premium
The Existence of a N→C Dative Bond in the C 60 –Piperidine Complex
Author(s) -
Lamanec Maximilián,
Lo Rabindranath,
Nachtigallová Dana,
Bakandritsos Aristides,
Mohammadi Elmira,
Dračínský Martin,
Zbořil Radek,
Hobza Pavel,
Wang Weizhou
Publication year - 2021
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.202012851
Subject(s) - piperidine , fullerene , hydrogen bond , carbon fibers , covalent bond , chemistry , lone pair , computational chemistry , crystallography , chemical physics , materials science , molecule , stereochemistry , organic chemistry , composite number , composite material
The complexes formed between carbon allotropes (C 20 , C 60 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 C 60 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.