Abstract
In this work, a σ-hole interaction is predicted theoretically in XH3Si···HMY complexes, where X=H, F, CN; M=Be, Mg and Y=H, F, CH3. The properties of this interaction, termed “tetrel-hydride” interaction, are investigated in terms of geometric, interaction energies, and electronic features of the complexes. The geometry of these complexes is obtained using the second-order Møller–Plesset perturbation theory (MP2) with aug-cc-pVTZ basis set. For each XH3Si···HMY complex, a tetrel-hydride bond is formed between the negatively charged H atom of HMY molecule and the positively charged Si atom of XH3Si molecule. The CCSD(T)/aug-cc-pVTZ interaction energies of this type of σ-hole bonding range from −0.6 to −3.8 kcal mol-1. The stability of XH3Si···HMY complexes is attributed mainly to electrostatic and correlation effects. The nature of tetrel-hydride interaction is analyzed with atoms in molecules (AIM) and natural bond orbital (NBO) theories.
Similar content being viewed by others
References
Jeffrey GA (1997) An introduction to hydrogen bonding. Oxford University Press, Oxford
Kabeláč M, Hobza P (2007) Hydration and stability of nucleic acid bases and base pairs. Phys Chem Chem Phys 9:903–917
Esrafili MD (2012) Characteristics and nature of the intermolecular interactions in boron-bonded complexes with carbene as electron donor: an ab initio, SAPT and QTAIM study. J Mol Model 18:2003–2011
Buckingham AD, Del Bene JE, McDowell SAC (2008) The hydrogen bond. Chem Phys Lett 463:1–10
Berka K, Laskowski R, Riley KE, Hobza P, Vondrášek J (2009) Representative amino acid side chain interactions in proteins. a comparison of highly accurate correlated ab initio quantum chemical and empirical potential procedures. J Chem Theory Comput 5:982–992
Fried SD, Bagchi S, Boxer SG (2013) Measuring electrostatic fields in both hydrogen-bonding and non-hydrogen-bonding environments using carbonyl vibrational probes. J Am Chem Soc 135:11181–11192
Esrafili MD, Juyban P (2014) CNXeCl and CNXeBr species as halogen bond donors: a quantum chemical study on the structure, properties, and nature of halogen···nitrogen interactions. J Mol Model 20:2203
Ueda K, Oguni M, Asaji T (2014) Halogen bond as controlling the crystal structure of 4-amino-3,5-dihalogenobenzoic acid and its effect on the positional ordering/disordering of acid protons. Cryst Growth Des 14:6189–6196
Wang C, Danovich D, Mo Y, Shaik S (2014) On the nature of the halogen bond. J Chem Theory Comput 10:3726–3737
Priimagi A, Cavallo G, Metrangolo P, Resnati G (2013) The halogen bond in the design of functional supramolecular materials: recent advances. Acc Chem Res 46:2686–2695
Forni A, Pieraccini S, Rendine S, Sironi M (2014) Halogen bonds with benzene: an assessment of DFT functionals. J Comput Chem 35:386–394
Robinson SW, Mustoe CL, White NG, Brown A, Thompson AL, Kennepohl P, Beer PD (2015) Evidence for halogen bond covalency in acyclic and interlocked halogen-bonding receptor anion recognition. J Am Chem Soc 137:499–507
Clark T, Hennemann M, Murray JS, Politzer P (2007) Halogen bonding: the σ-hole. J Mol Model 13:291–296
Politzer P, Lane P, Concha MC, Ma YG, Murray JS (2007) An overview of halogen bonding. J Mol Model 13:305–311
Politzer P, Murray JS, Concha MC (2007) Halogen bonding and the design of new materials: organic bromides, chlorides and perhaps even fluorides as donors. J Mol Model 13:643–650
Murray JS, Concha MC, Lane P, Hobza P, Politzer P (2008) Blue shifts vs red shifts in σ-hole bonding. J Mol Model 14:699–704
Politzer P, Murray JS, Concha MC (2008) σ-hole bonding between like atoms; a fallacy of atomic charges. J Mol Model 14:659–665
Riley KE, Murray JS, Fanfrlík J, Řezáč J, Solá RJ, Concha MC, Ramos FM, Politzer P (2011) Halogen bond tunability I: the effects of aromatic fluorine substitution on the strengths of halogen-bonding interactions involving chlorine, bromine, and iodine. J Mol Model 17:3309–3318
Politzer P, Riley KE, Bulat FA, Murray JS (2012) Perspectives on halogen bonding and other σ-hole interactions: Lex parsimoniae (Occam’s Razor). Comput Theor Chem 998:2–8
Murray JS, Lane P, Clark T, Riley KE, Politzer P (2012) σ-Holes, π-holes and electrostatically-driven interactions. J Mol Model 18:541–548
Politzer P, Murray JS (2012) Halogen bonding and beyond: factors influencing the nature of CN–R and SiN–R complexes with F–Cl and Cl2. Theor Chem Acc 131:1114
Politzer P, Murray JS (2013) Halogen bonding: an interim discussion. ChemPhysChem 14:278–294
Politzer P, Murray JS, Clark T (2013) Halogen bonding and other σ-hole interactions: a perspective. Phys Chem Chem Phys 15:11178–11189
Murray JS, Lane P, Politzer P (2013) Expansion of the σ-hole concept. J Mol Model 15:723–729
Wang WZ, Ji BM, Zhang Y (2009) Chalcogen bond: a sister noncovalent bond to halogen bond. J Phys Chem A 113:8132–8135
Brezgunova ME, Lieffrig J, Aubert E, Dahaoui S, Fertey P, Lebègue S, Ángyán JG, Fourmigué M, Espinosa E (2013) Chalcogen bonding: experimental and theoretical determinations from electron density analysis. Geometrical preferences driven by electrophilic–nucleophilic interactions. Cryst Growth Des 13:3283–3289
Esrafili MD, Vakili M, Solimannejad M (2014) Cooperativity effects between σ-hole interactions: a theoretical evidence for mutual influence between chalcogen bond and halogen bond interactions in F2S···NCX···NCY complexes (X=F, Cl, Br, I; Y = H, F, OH). Mol Phys 112:2078–2084
Politzer P, Murray JS, Janjić GV, Zarić SD (2013) σ-Hole interactions of covalently-bonded nitrogen, phosphorus and arsenic: a survey of crystal structures. Crystal 4:12–31
Scheiner S (2013) Detailed comparison of the pnicogen bond with chalcogen, halogen, and hydrogen bonds. Int J Quantum Chem 113:1609–1620
Esrafili MD, Vakili M, Solimannejad M (2014) Cooperative effects in pnicogen bonding: (PH2F)2–7 and (PH2Cl)2–7 clusters. Chem Phys Lett 609:37–41
Bauza A, Mooibroek TJ, Frontera A (2013) Tetrel-bonding interaction: rediscovered supramolecular force. Angew Chem Int Ed 52:12317–12321
Mani D, Arunan E (2013) The X–C···Y (X = O/F, Y = O/S/F/Cl/Br/N/P) ‘carbon bond’ and hydrophobic interactions. Phys Chem Chem Phys 15:14377–14383
Mani D, Arunan E (2013) Microwave spectroscopic and atoms in molecules theoretical investigations on the Ar···propargyl alcohol complex: Ar···H–O, Ar···π, and Ar···C interactions. ChemPhysChem 14:754–763
Bundhun A, Ramasami P, Murray JS, Politzer P (2013) Trends in σ-hole strengths and interactions of F3MX molecules (M= C, Si, Ge and X = F, Cl, Br, I). J Mol Model 19:2739–2746
Grabowski SJ (2014) Tetrel bond–σ-hole bond as a preliminary stage of the SN2 reaction. Phys Chem Chem Phys 16:1824–1834
Li Q, Guo X, Yang X, Li W, Cheng J, Li H (2014) A σ-hole interaction with radical species as electron donors: does single-electron tetrel bonding exist? Phys Chem Chem Phys 16:11617–11625
Esrafili MD, Solimannejad M (2013) Revealing substitution effects on the strength and nature of halogen-hydride interactions: a theoretical study. J Mol Model 19:3767–3777
Schmidt MW, Baldridge KK, Boatz JA, Elbert ST, Gordon MS, Jensen JH, Koseki S, Matsunaga N, Nguyen KA, Su SJ, Windus TL, Dupuis M, Montgomery JA (1993) General atomic and molecular electronic structure system. J Comput Chem 14:1347–1363
Boys SF, Bernardi F (1970) The calculation of small molecular interactions by the differences of separate total energies. Some procedures with reduced errors. Mol Phys 19:553–566
Su P, Li H (2009) Energy decomposition analysis of covalent bonds and intermolecular interactions. J Chem Phys 131:014102
Bulat FA, Toro-Labbe A, Brinck T, Murray JS, Politzer P (2010) Quantitative analysis of molecular surfaces: areas, volumes, electrostatic potentials and average local ionization energies. J Mol Model 16:1679–1691
Reed AE, Curtiss LA, Weinhold F (1988) Intermolecular interactions from a natural bond orbital, donor-acceptor viewpoint. Chem Rev 88:899–926
Bader RFW (1990) Atoms in molecules-a quantum theory. Oxford University Press, New York
Biegler-Konig F, Schonbohm J, Bayles D (2001) AIM 2000. J Comput Chem 22:545–559
Esrafili MD, Ahmadi B (2012) A theoretical investigation on the nature of Cl···N and Br···N halogen bonds in F-Ar-X···NCY complexes (X = Cl, Br and Y = H, F, Cl, Br, OH, NH2, CH3 and CN). Comput Theor Chem 997:77–82
Esrafili MD, Mohammadirad N (2013) Insights into the strength and nature of carbene···halogen bond interactions: a theoretical perspective. J Mol Model 19:2559–2566
Esrafili MD, Fatehi P, Solimannejad M (2014) Mutual interplay between pnicogen bond and dihydrogen bond in HMH···HCN···PH2X complexes (M = Be, Mg, Zn; X = H, F, Cl). Comput Theor Chem 1034:1–6
Esrafili MD, Mohammadian-Sabet F, Solimannejad M (2014) A theoretical evidence for mutual influence between S···N(C) and hydrogen/lithium/halogen bonds: competition and interplay between p-hole and r-hole interactions. Struct Chem 25:1197–1205
Bondi A (1964) van der Waals volumes and radii. J Phys Chem 68:441–451
Li Q, Qi H, Li R, Liu X, Li W, Cheng J (2012) Prediction and characterization of a chalcogen–hydride interaction with metal hybrids as an electron donor in F2CS–HM and F2CSe–HM (M = Li, Na, BeH, MgH, MgCH3) complexes. Phys Chem Chem Phys 14:3025–3030
Politzer P, Murray JS, Clark T (2014) σ-Hole bonding: a physical interpretation. Top Curr Chem. doi:10.1007/128_2014_568
Koch U, Popelier PLA (1995) Characterization of C-H···O hydrogen bonds on the basis of the charge density. J Phys Chem 99:9747–9754
Lipkowski P, Grabowski SJ, Robinson TL, Leszczynski J (2004) Properties of the C−H···H dihydrogen bond: an ab initio and topological analysis. J Phys Chem A 108:10865–10872
Esrafili MD, Mahdavinia G, Javaheri M, Sobhi HR (2014) A theoretical study of substitution effects on halogen–π interactions. Mol Phys 112:1160–1166
Rozas I, Alkorta I, Elguero (2000) Behaviour of ylides containing N, O and C atoms as hydrogen bond acceptors. J Am Chem Soc 122:11154–11161
Author information
Authors and Affiliations
Corresponding author
Electronic supplementary material
Below is the link to the electronic supplementary material.
Fig. S1
(DOC 4595 kb)
Rights and permissions
About this article
Cite this article
Esrafili, M.D., Mohammadian-Sabet, F. Exploring σ-hole bonding in XH3Si···HMY (X=H, F, CN; M=Be, Mg; Y=H, F, CH3) complexes: a “tetrel-hydride” interaction. J Mol Model 21, 60 (2015). https://doi.org/10.1007/s00894-015-2614-4
Received:
Accepted:
Published:
DOI: https://doi.org/10.1007/s00894-015-2614-4