Issue 3, 2016

1,1,2,2-Tetracyanocyclopropane (TCCP) as supramolecular synthon


The 1,1,2,2-tetracyanocyclopropane (TCCP) unit presents a synthetically accessible and versatile synthon that can interact with lone-pair or π-electrons by ‘non-covalent carbon bonding’. Complexes of TCCP with common small molecules, anions, aromatics like fullerenes, amino acids and nucleobases were computed at the DFT BP86-D3/def2-TZVP level of theory. Binding energies vary between about −10 kcal mol−1 for neutral guests and −15 to −50 kcal mol−1 for anionic species. This is comparable to strong and very strong hydrogen bonding respectively. Thus, in addition to synthons that contain polarized hydrogen or halogen atoms, TCCP presents a new supramolecular synthon that awaits experimental exploitation.

Graphical abstract: 1,1,2,2-Tetracyanocyclopropane (TCCP) as supramolecular synthon

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Article information

Article type
20 Oct 2015
08 Dec 2015
First published
09 Dec 2015
This article is Open Access
Creative Commons BY license

Phys. Chem. Chem. Phys., 2016,18, 1693-1698

Author version available

1,1,2,2-Tetracyanocyclopropane (TCCP) as supramolecular synthon

A. Bauzá, A. Frontera and T. J. Mooibroek, Phys. Chem. Chem. Phys., 2016, 18, 1693 DOI: 10.1039/C5CP06350G

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