Observations of Tetrel Bonding Between Sp-carbon and THF

Overview

Journal Chem Sci

Publisher Royal Society of Chemistry

Specialty Chemistry

Date 2021 Jun 14

PMID 34122986

Citations 11

Authors

Victoria L Heywood

Thomas P J Alford

Julius J Roeleveld

Siebe J Lekanne Deprez

Abraham Verhoofstad

Jarl Ivar van der Vlugt

Sergio R Domingos

Melanie Schnell

Anthony P Davis

Tiddo J Mooibroek

Affiliations

Soon will be listed here.

Abstract

We report the direct observation of tetrel bonding interactions between sp-carbons of the supramolecular synthon 3,3-dimethyl-tetracyanocyclopropane () and tetrahydrofuran in the gas and crystalline phase. The intermolecular contact is established σ-holes and is driven mainly by electrostatic forces. The complex manifests distinct binding geometries when captured in the crystalline phase and in the gas phase. We elucidate these binding trends using complementary gas phase quantum chemical calculations and find a total binding energy of -11.2 kcal mol for the adduct. Our observations pave the way for novel strategies to engineer sp-C centred non-covalent bonding schemes for supramolecular chemistry.

Citing Articles

The Tetrel Bonds of Hypervalent Halogen Compounds.

Niu Z, McDowell S, Li Q Molecules. 2023; 28(20).

PMID: 37894566 PMC: 10609133. DOI: 10.3390/molecules28207087.

Static and Dynamical Quantum Studies of CX-AlX and CSiX-BX (X = F, Cl, Br) Complexes with Hydrocyanic Acid: Unusual Behavior of Strong π-Hole at Triel Center.

Michalczyk M, Wojtkowiak K, Panek J, Jezierska A, Zierkiewicz W Int J Mol Sci. 2023; 24(9).

PMID: 37175586 PMC: 10177972. DOI: 10.3390/ijms24097881.

Computational Study of Driving Forces in ATSP, PDIQ, and P53 Peptide Binding: C═O···C═O Tetrel Bonding Interactions at Work.

Lang L, Frontera A, Perez A, Bauza A J Chem Inf Model. 2023; 63(10):3018-3029.

PMID: 37014944 PMC: 10207270. DOI: 10.1021/acs.jcim.3c00024.

Substituent Effects in Tetrel Bonds Involving Aromatic Silane Derivatives: An ab initio Study.

Burguera S, Frontera A, Bauza A Molecules. 2023; 28(5).

PMID: 36903636 PMC: 10004842. DOI: 10.3390/molecules28052385.

The Relevance of Experimental Charge Density Analysis in Unraveling Noncovalent Interactions in Molecular Crystals.

Thomas S, Dikundwar A, Sarkar S, Pavan M, Pal R, Hathwar V Molecules. 2022; 27(12).

PMID: 35744821 PMC: 9229234. DOI: 10.3390/molecules27123690.

References

Vik E, Li P, Pellechia P, Shimizu K . Transition-State Stabilization by n→π* Interactions Measured Using Molecular Rotors. J Am Chem Soc. 2019; 141(42):16579-16583. DOI: 10.1021/jacs.9b08542. View

Harder M, Kuhn B, Diederich F . Efficient stacking on protein amide fragments. ChemMedChem. 2013; 8(3):397-404. DOI: 10.1002/cmdc.201200512. View

Scheiner S . The pnicogen bond: its relation to hydrogen, halogen, and other noncovalent bonds. Acc Chem Res. 2012; 46(2):280-8. DOI: 10.1021/ar3001316. View

Contreras-Garcia J, Johnson E, Keinan S, Chaudret R, Piquemal J, Beratan D . NCIPLOT: a program for plotting non-covalent interaction regions. J Chem Theory Comput. 2011; 7(3):625-632. PMC: 3080048. DOI: 10.1021/ct100641a. View

Bauza A, Mooibroek T, Frontera A . Influence of ring size on the strength of carbon bonding complexes between anions and perfluorocycloalkanes. Phys Chem Chem Phys. 2014; 16(36):19192-7. DOI: 10.1039/c4cp01983k. View

van der Lubbe S, Fonseca Guerra C . The Nature of Hydrogen Bonds: A Delineation of the Role of Different Energy Components on Hydrogen Bond Strengths and Lengths. Chem Asian J. 2019; 14(16):2760-2769. PMC: 6771679. DOI: 10.1002/asia.201900717. View

Juanes M, Saragi R, Caminati W, Lesarri A . The Hydrogen Bond and Beyond: Perspectives for Rotational Investigations of Non-Covalent Interactions. Chemistry. 2019; 25(49):11402-11411. DOI: 10.1002/chem.201901113. View

Murray J, Lane P, Politzer P . Expansion of the sigma-hole concept. J Mol Model. 2008; 15(6):723-9. DOI: 10.1007/s00894-008-0386-9. View

Bauza A, Frontera A, Mooibroek T . 1,1,2,2-Tetracyanocyclopropane (TCCP) as supramolecular synthon. Phys Chem Chem Phys. 2015; 18(3):1693-8. DOI: 10.1039/c5cp06350g. View

10.

Pierrefixe S, Poater J, Im C, Bickelhaupt F . Hypervalent versus nonhypervalent carbon in noble-gas complexes. Chemistry. 2008; 14(23):6901-11. DOI: 10.1002/chem.200800013. View

11.

Gao S, Obenchain D, Lei J, Feng G, Herbers S, Gou Q . Tetrel bonds and conformational equilibria in the formamide-CO complex: a rotational study. Phys Chem Chem Phys. 2019; 21(13):7016-7020. DOI: 10.1039/c9cp00055k. View

12.

Dutta J, Sahoo D, Jena S, Tulsiyan K, Biswal H . Non-covalent interactions with inverted carbon: a carbo-hydrogen bond or a new type of hydrogen bond?. Phys Chem Chem Phys. 2020; 22(16):8988-8997. DOI: 10.1039/d0cp00330a. View

13.

Metrangolo P, Neukirch H, Pilati T, Resnati G . Halogen bonding based recognition processes: a world parallel to hydrogen bonding. Acc Chem Res. 2005; 38(5):386-95. DOI: 10.1021/ar0400995. View

14.

Grabowski S . Hydrogen and halogen bonds are ruled by the same mechanisms. Phys Chem Chem Phys. 2013; 15(19):7249-59. DOI: 10.1039/c3cp50537e. View

15.

Mikosch J, Trippel S, Eichhorn C, Otto R, Lourderaj U, Zhang J . Imaging nucleophilic substitution dynamics. Science. 2008; 319(5860):183-6. DOI: 10.1126/science.1150238. View

16.

Bartlett G, Choudhary A, Raines R, Woolfson D . n-->pi* interactions in proteins. Nat Chem Biol. 2010; 6(8):615-20. PMC: 2921280. DOI: 10.1038/nchembio.406. View

17.

Bauza A, Mooibroek T, Frontera A . The bright future of unconventional σ/π-hole interactions. Chemphyschem. 2015; 16(12):2496-517. DOI: 10.1002/cphc.201500314. View

18.

Maccallum P, POET R . Coulombic attractions between partially charged main-chain atoms stabilise the right-handed twist found in most beta-strands. J Mol Biol. 1995; 248(2):374-84. DOI: 10.1016/s0022-2836(95)80057-3. View

19.

Bauza A, Mooibroek T, Frontera A . Small cycloalkane (CN)2C-C(CN)2 structures are highly directional non-covalent carbon-bond donors. Chemistry. 2014; 20(33):10245-8. DOI: 10.1002/chem.201403680. View

20.

Lee , Yang , PARR . Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density. Phys Rev B Condens Matter. 1988; 37(2):785-789. DOI: 10.1103/physrevb.37.785. View