Abstract
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.
Highlights
Living matter is for a great part governed by intermolecular recognition phenomena such as substrate/inhibitor/protein binding,[1,2,3,4] signalling events[5,6,7,8] and cell–cell interactions.[9,10,11] Intramolecular phenomena such as the folding of proteins[12,13,14] or DNA/RNA15–18 are governed by the same physical forces
Underpinning the design process is knowing which molecular fragments will engage in favourable intermolecular interactions, i.e. knowing which supramolecular synthons one can use.[31,32,33]
For our enquiries we conducted computations based on density functional theory (DFT) at the BP86-D3/def2-TZVP level of theory and Table 1 summarized the results of the interaction of TCCP with common small molecules
Summary
Living matter is for a great part governed by intermolecular recognition phenomena such as substrate/inhibitor/protein binding,[1,2,3,4] signalling events[5,6,7,8] and cell–cell interactions.[9,10,11] Intramolecular phenomena such as the folding of proteins[12,13,14] or DNA/RNA15–18 are governed by the same physical forces. The complexation energy with the control guest methane (À2.3 kcal molÀ1) is very small and methane is not located in the electron poor binding pocket of TCCP (see Fig. S1, ESI†).
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