Non-covalent interactions with inverted carbon: a carbo-hydrogen bond or a new type of hydrogen bond?

Abstract

Crystal structure analysis and quantum chemical calculations enabled us to discover a new non-covalent interaction, coined as carbo-hydrogen bond (CH-bond).

Observations of tetrel bonding between sp3-carbon and THF

“…[29][30][31][32] Non-covalent interactions with sp 3 -hybridized carbon atoms are implicated in the advent of canonical S N 2 nucleophilic displacement reactions 12,[33][34][35] and can persist with methyl groups in crystal structures. [36][37][38] However, a supramolecular synthon to predictably generate directional tetrel-bonding interactions centred on sp 3 -C has not yet been experimentally disclosed. We envisaged that 1,1,2,2tetracyanocyclopropane (TCCP) derivatives could full this role.…”

Förster Resonance Energy Transfer from Carbon Nanoparticles to a DNA-Bound Compound: A Method to Detect the Nature of Binding

“…An additional carbon hydrogen nonbonding interaction (3.69 Å) is present between C-2 of the pyrrolidine moiety of EPSBT and H of one of the O–H groups in the phosphate backbone. This kind of C–H interaction may help in retaining EPSBT in the binding pocket for a longer time …”

“…This kind of C−H interaction may help in retaining EPSBT in the binding pocket for a longer time. 58 EPSBT satisfactorily binds to the GTCTT region of the sequence of X2 (5′-GTCTTTGT-3′). It mainly binds to the guanine and thymine bases.…”

Noncovalent interactions in proteins and nucleic acids: beyond hydrogen bonding and π-stacking

“…161 Biswal and co-workers first reported a new kind of NCI where 'to and fro' ss* interactions occur. 6 They observed it where strained carbocyclic compounds having inverted carbon (C i ) interact with the p-block elements' hydrides (HX) and named it 'carbo-hydrogen bonding' (C H -bonding). The geometrical criteria for this interaction are described in Fig.…”

“…For example, (I) the role of X-bonding in halogen-based drugs in regulating membrane ion transport and cancer inhibition; 18,19 (II) Chbonding in the ebselen moiety helps in inhibiting Mpro, a key enzyme responsible for replicating the SARS-CoV-2 virus; 20,21 (III) C-bonding helps in photo-dissociation of myoglobin via the transmission of the heme doming oscillation in carbomonoxy myoglobin; 22 and (IV) C H -bonding in tuning the kinetics of enzymatic catalysis. 6 The seminal contributions mentioned above impel a comprehensive review of such NCIs and their significance in biomolecules. Several reviews have been published on noncovalent interactions such as halogen bonding, 23 chalcogen bonding, 24 pnictogen bonding, 25 and tetrel bonding; 26 most of them are based on their applications in crystallography, synthetic chemistry, and materials chemistry.…”