Abstract
The field of intra- and intermolecular interactions has received a major boost in the past one decade. Significant advances in both instrumentation (for experimental purposes) and computational resources (development of theoretical models) have provided strong impetus to this area of research. The understanding of the nature, energetics and the topological characteristics of these interactions are the driving forces which govern intermolecular recognition. This is strongly dependent on the state of aggregation of the substance. The environment (solid, liquid and gas) plays an extremely crucial and subtle role in deciphering the mechanism via which molecules interact with each other. In the past two decades, there has been rigorous development in the understanding of strong hydrogen bonds. The focus has now shifted towards the quantitative assessment of weak intermolecular interactions, of the type C–H···X (X = F in particular), X···X, X(lp)···π along with σ–hole-directed intermolecular interactions involving tetrels, chalcogens, pnictogens, halogens and the aerogens. In addition, there is increasing evidence for the assessment of the relevance of π–hole-based interactions in tetrels, chalcogens, and pnictogens as well. The current perspective highlights the importance of the above-mentioned interactions and their associated electronic features. This has strong implications in the area of materials and related applied sciences with relevance towards the technological applications of these interactions in terms of understanding structure–property correlation in the mechanical, optical and electrical properties of matter.
Similar content being viewed by others
References
Chopra D (2018) Understanding intermolecular interactions in the solid state: approaches and techniques. Royal Society of Chemistry, London
Desiraju GR, Steiner T (2001) The weak hydrogen bond in structural chemistry and biology. Oxford University Press Inc., New York
Gilli G, Gilli P (2009) The nature of hydrogen bond: outline of a comprehensive hydrogen bond theory. Oxford University Press, New York
Arunan E et al (2011) Definition of the hydrogen bond (IUPAC Recommendations 2011). Pure Appl Chem 83:1637
Hathwar VR et al (2014) Revealing the polarizability of organic fluorine in the trifluoromethyl group: implications in supramolecular chemistry. Cryst Growth Des 14:5366
Munshi P, Guru Row TN (2005) Exploring the lower limit in hydrogen bonds: analysis of weak C–H···O and C–H···π interactions in substituted coumarins from charge density analysis. J Phys Chem A 109:659
Mondal PK, Chopra D (2018) Role of halogen-involved intermolecular interactions and existence of isostructurality in the crystal packing of —CF3 and halogen (Cl or Br or I) substituted benzamides. Acta Cryst B 74:574
Jeffrey GA, Takagi S (1978) Hydrogen-bond structure in carbohydrate crystals. Acc Chem Res 11:264
Grabowski SJ (2017) Hydrogen bonds, and σ–hole and π–hole bonds—mechanisms protecting doublet and octet electron structures. Phys Chem Chem Phys 19:29742
Politzer P, Murray JS (2013) Halogen bonding: an interim discussion. Chem Phys Chem 14:278
Clark T et al (2007) Halogen bonding: the σ–hole. J Mol Model 13:291
Politzer P et al (2013) Halogen bonding and other σ–hole interactions: a perspective. Phys Chem Chem Phys 15:11178
Politzer P, Murray JS (2017) Sigma–hole interactions: perspectives and misconceptions. Crystals 7:212
Wang H et al (2016) σ–hole bond vs π–hole bond: a comparison based on halogen bond. Chem Rev 116:5072
Neaton JB (2017) A direct look at halogen bonds, high-resolution images of halogen-containing molecules reveal unusual bonding patterns. Science 358:167
Pascoe DJ et al (2017) The origin of chalcogen-bonding interactions. J Am Chem Soc 139:15160
Scheiner S (2013) The pnicogen bond: its relation to hydrogen, halogen, and other noncovalent bonds. Acc Chem Res 46:280
Quinonero D (2017) Sigma–hole carbon-bonding interactions in carbon–carbon double bonds: an unnoticed contact. Phys Chem Chem Phys 19:15530
Grabowski SJ (2014) Tetrel bond–σ hole bond as a preliminary stage of the SN2 reaction. Phys Chem Chem Phys 16:1824
Grabowski SJ (2014) Halogen bond with the multivalent halogen acting as the Lewis acid center. Chem Phys Lett 605–606:131
Riera AB (2017) On the importance of σ-/π–hole interaction in chemistry and in biochemistry. Ph.D. thesis, University of Balearic Islands, Balearic Islands, Spain
Politzer P et al (2010) Halogen bonding: an electrostatically-driven highly directional noncovalent interaction. Phys Chem Chem Phys 12:7748
Riley KE, Hobza P (2013) The relative roles of electrostatics and dispersion in the stabilization of halogen bonds. Phys Chem Chem Phys 15:17742
Lipkowski P et al (2006) Properties of the halogen-hydride interaction: an ab initio and “atoms in molecules” analysis. J Phys Chem A 110:10296
Guthrie F (1863) On the iodide of iodammonium. J Chem Soc 16:239
Hassel O, Hvoslef J (1954) Direct structural evidence for weak charge transfer bond in solid containing chemically structured molecule. Acta Chem Scand 8:873
Hassel O, Romming C (1962) Direct structural evidence for weak charge transfer bonds in solids containing chemically saturated molecules. Q Rev Chem Soc 16:1
Hassel O (1970) Structural aspects of interatomic charge-transfer bonding. Science 170:497
Brinck T et al (1992) Surface electrostatic potentials of halogenated methanes as indicators of directional intermolecular interactions. Int J Quantum Chem 44:57
Desiraju GR et al (2013) Definition of the halogen bond (IUPAC Recommendations 2013. Pure Appl Chem 85:1711
Chopra D (2012) Is organic fluorine really “not” polarizable? Cryst Growth Des 12:541
Sirohiwal A et al (2017) Characterization of fluorine-centred ‘F···O’ σ–hole interactions in the solid state. Acta Cryst B. 73:140
Costa PJ (2017) The halogen bond: nature and applications. Phys Sci Rev 2:20170136
Voth AR (2009) Halogen bonds as orthogonal molecular interactions to hydrogen bonds. Nat Chem 1:74
Lommerse JPM et al (1996) The nature and geometry of intermolecular interactions between halogens and oxygen or nitrogen. J Am Chem Soc 118:3108
Riley KE et al (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
Riley KE et al (2009) Br···O complexes as probes of factors affecting halogen bonding: interactions of bromobenzenes and bromopyrimidines with acetone. J Chem Theory Comput 5:155
Krawczuk A et al (2014) PolaBer: a program to calculate and visualize distributed atomic polarizabilities based on electron density partitioning. J Appl Cryst 47:1452
Riley KE et al (2013) Halogen bond tunability II: the varying roles of electrostatic and dispersion contributions to attraction in halogen bonds. J Mol Model 19:4651
Desiraju GR, Parthasarathy RJ (1989) The nature of halogen–halogen interactions: are short halogen contacts due to specific attractive forces or due to close packing of nonspherical atoms? J Am Chem Soc 111:8725
Metrangolo P, Resnati G (2014) Type II halogen···halogen contacts are halogen bonds. IUCrJ. 1:5
Wolters LP et al (2014) The many faces of halogen bonding: a review of theoretical models and methods. Comput Mol Sci 4:523
Palusiak M (2010) On the nature of halogen bond—the Kohn–Sham molecular orbital approach. J Mol Struct (Theochem) 945:89
Rosokha SV, Traversa A (2015) From charge transfer to electron transfer in halogen-bonded complexes of electrophilic bromocarbons with halide anions. Phys Chem Chem Phys 17:4989
Cabot R, Hunter CA (2009) Non-covalent interactions between iodo-perfluorocarbons and hydrogen bond acceptors. Chem Commun (15):2005–2007
Wolters LP, Bickelhaupt FM (2012) Halogen bonding versus hydrogen bonding: a molecular orbital perspective. Chem Open 1:96
Lindblad S et al (2018) Halogen bond asymmetry in solution. J Am Chem Soc 140:13503
Oliveira V et al (2016) The intrinsic strength of the halogen bond: electrostatic and covalent contributions described by coupled cluster theory. Phys Chem Chem Phys 18:33031
Oliveira V et al (2017) Quantitative assessment of halogen bonding utilizing vibrational spectroscopy. Inorg Chem 56:488
Duarte DJR (2016) Halogen bonding. The role of the polarizability of the electron-pair donor. Phys Chem Chem Phys 18:7300
Stone AJ (2017) Natural bond orbitals and the nature of the hydrogen bond. J Phys Chem A 121:1531
Wang JW (2017) Halogen-bonding contacts determining the crystal structure and fluorescence properties of organic salts. New J Chem 41:9444
Khavasi HR, Tehrani AA (2013) Halogen bonding synthon crossover in conformational polymorphism. CrystEngComm 15:5813
Noa FMA et al (2017) Halogen-bonding, isomorphism, polymorphism, and kinetics of enclathration in host−guest compounds. Cryst Growth Des 17:4647
Christopherson JC (2018) Halogen-bonded cocrystals as optical materials: next-generation control over light−matter interactions. Cryst Growth Des 18:1245
Bennington JC (2016) Isostructural cocrystals of 1,3,5-trinitrobenzene assembled by halogen bonding. Cryst Growth Des 16:4688
Mukherjee A, Desiraju GR (2014) Halogen bonds in some dihalogenated phenols: applications to crystal engineering IUCrJ 1:49
Erdelyi M (2017) Application of the halogen bond in protein systems. Biochemistry 56:2759
Rosenfield RE Jr et al (1977) Directional preferences of nonbonded atomic contacts with divalent sulfur. 1. Electrophiles and nucleophiles. J Am Chem Soc 99:4860
Parthasarathy R, Row TNG (1981) Directional preferences of nonbonded atomic contacts with divalent sulfur in terms of its orbital orientations. 2. S–S interactions and nonspherical shape of sulfur in crystals. J Am Chem Soc 103:477
Burling FT, Goldstein BM (1992) Computational studies of nonbonded sulfur-oxygen and selenium-oxygen interactions in the thiazole and selenazole nucleosides. J Am Chem Soc 114:2313
Nagao Y et al (1998) Intramolecular nonbonded S···O interaction recognized in (acylimino)thiadiazoline derivatives as angiotensin ii receptor antagonists and related compounds. J Am Chem Soc 120:3104
Murray JS et al (2007) σ–hole bonding: molecules containing group VI atoms. J Mol Model 13:1033
Murray JS et al (2008) Simultaneous σ–hole and hydrogen bonding by sulfur- and selenium-containing heterocycles. Int J Quantum Chem 108:2770
Shukla R, Chopra D (2016) Crystallographic and theoretical investigation on the nature and characteristics of type I C=S···S=C interactions. Cryst Growth Des 16:6734
Wang W et al (2009) Chalcogen bond: a sister noncovalent bond to halogen bond. J Phys Chem A 113:8132
Murray JS et al (2009) Expansion of the σ–hole concept. J Mol Model 15:723
Pecina A et al (2015) Chalcogen and pnicogen bonds in complexes of neutral icosahedral and bicapped square-antiprismatic heteroboranes. J Phys Chem A 119:1388
Iwaoka M et al (2002) Statistical and theoretical investigations on the directionality of nonbonded S···O interactions. Implications for molecular design and protein engineering. J Am Chem Soc 124:10613
Iwaoka M et al (2001) Statistical characterization of nonbonded S···O interactions in proteins. Chem Lett 30:132
Mahmudov KT et al (2017) Chalcogen bonding in synthesis, catalysis and design of materials. Dalton Trans 46:10121
Benz S et al (2016) Anion transport with chalcogen bonds. J Am Chem Soc 138:9093
Knight FR et al (2010) Hypervalent adducts of chalcogen-containing peri-substituted naphthalenes; reactions of sulfur, selenium, and tellurium with dihalogens. Inorg Chem 49:7577
Chivers T, Konu J (2009) Ligand-stabilized chalcogen dications. Angew Chem Int Ed 48:3025
Kusamoto T (2013) Utilization of σ–holes on sulfur and halogen atoms for supramolecular cation···anion interactions in bilayer Ni(dmit)2 anion radical salts. Cryst Growth Des 13:4533
Adhikari U, Scheiner S (2014) Effects of charge and substituent on the S···N chalcogen bond. J Phys Chem 118:3183
Alikhani E et al (2014) Topological reaction sites—very strong chalcogen bonds. Phys Chem Chem Phys 16:2430
Sanz P (2003) Resonance-assisted intramolecular chalcogen–chalcogen interactions? Chem Eur J 9:4548
Fourmigue M, Batail P (2004) Activation of hydrogen- and halogen-bonding interactions in tetrathiafulvalene-based crystalline molecular conductors. Chem Rev 104:5379
Bhandary S et al (2018) Dispersion stabilized Se/Te···π double chalcogen bonding synthons in in situ cryocrystallized divalent organochalcogen liquids. Cryst Growth Des 18:3734
Biot N, Bonifazi D (2018) Programming recognition arrays through double chalcogen-bonding interactions. Chem Eur J 24:5439
Cavallo G et al (2016) The halogen bond. Chem Rev 116:2478
Morgan RS et al (1978) Chains of alternating sulfur and π-bonded atoms in eight small proteins. Int J Pept Protein Res 11:209
Tauer TP (2005) Estimates of the ab initio limit for sulfur−π interactions: the H2S−benzene dimer. J. Phys. Chem. 109:191
Karshikoff A (2006) Non-covalent interactions in proteins. Imperial College Press, Singapore
Alvarez S (2013) A cartography of the van der Waals territories. Dalton Trans 42:8617
Bondi A et al (1964) van der Waals volumes and radii. J Phys Chem 68:441
Werz DB et al (2002) Nanotube formation favored by chalcogen–chalcogen interactions. J Am Chem Soc 124:10638
Gonzalez FV et al (2010) Stereoisomerization of β-hydroxy-α-sulfenyl-γ-butyrolactones controlled by two concomitant 1,4-type nonbonded sulfur-oxygen interactions as analyzed by X-ray crystallography. J Org Chem 75:5888
Shuvaev KV et al (2008) NC–(CF2)4–CNSSN· containing 1,2,3,5-dithiadiazolyl radical dimer exhibiting triplet excited states at low temperature and thermal hysteresis on melting–solidification: structural, spectroscopic, and magnetic characterization. Dalton Trans 14:4029
Menichetti S et al (2016) Role of noncovalent sulfur···oxygen interactions in phenoxyl radical stabilization: synthesis of super tocopherol-like antioxidants. Org Lett 18:5464
Mikherdov AS et al (2016) Difference in energy between two distinct types of chalcogen bonds drives regioisomerization of binuclear (diaminocarbene) PdII complexes. J Am Chem Soc 138:14129
Benz S et al (2017) Catalysis with chalcogen bonds. Angew Chem Int Ed 56:812
Robinson ERT et al (2013) Anhydrides as a,b-unsaturated acyl ammonium precursors: isothiourea-promoted catalytic asymmetric annulation processes. Chem Sci 4:2193
Fukata Y et al (2015) Facile net cycloaddition approach to optically active 1,5-benzothiazepines. J Am Chem Soc 137:5320
Manna D, Mugesh G (2012) Regioselective deiodination of thyroxine by iodothyronine deiodinase mimics: an unusual mechanistic pathway involving co-operative chalcogen and halogen bonding. J Am Chem Soc 134:4269
Robinson ERT et al (2016) Non-bonding 1,5-S/O interactions govern chemo and enantioselectivity in isothiourea-catalyzed annulations of benzazoles. Chem Sci 7:6919
Kojima T et al (2004) Synthesis and characterization of dibenzodioxadiselenafulvalene. J Org Chem 69:9319
Dutton JL et al (2009) Synthesis of N,C bound sulfur, selenium, and tellurium heterocycles via the reaction of chalcogen halides with –CH3 substituted diazabutadiene ligands. Inorg Chem 48:3239
Knight FR et al (2012) Noncovalent interactions in peri-substituted chalconium acenaphthene and naphthalene salts: a combined experimental, crystallographic, computational, and solid-state NMR study. Inorg Chem 51:11087
Thomas SP et al (2015) “Conformational simulation” of sulfamethizole by molecular complexation and insights from charge density analysis: role of intramolecular S···O chalcogen bonding. Cryst Growth Des 15:2110
Garrett GE et al (2016) Anion recognition by a bidentate chalcogen bond donor. Chem Commun 52:9881
Suzuki T et al (1992) Clathrate formation and molecular recognition by novel chalcogen-cyano interactions in tetracyanoquinodimethanes fused with thiadiazole and selenadiazole rings. J Am Chem Soc 114:3034
Zhao H, Gabbaï F (2010) A bidentate Lewis acid with a telluronium ion as an anion-binding site. Nat Chem 2:984
Jentzsch AV et al (2013) Synthetic ion transporters that work with anion–π interactions, halogen bonds, and anion–macrodipole interactions. Acc Chem Res 46:2791
Beno BR et al (2015) A survey of the role of noncovalent sulfur interactions in drug design. J Med Chem 58:4383
Bauer S et al (2009) Enantiomerically pure bis(phosphanyl)carbaborane(12) compounds. Eur J Inorg Chem. https://doi.org/10.1002/ejic.200900304
Hill WE, Silva-Trivino LM (1979) Preparation and characterization of di(tertiary phosphines) with electronegative substituents. 2. Unsymmetrical derivatives. Inorg Chem 18:361
Kilian P et al (2003) Naphthalene-1,8-diyl bis(halogenophosphanes): novel syntheses and structures of useful synthetic building blocks. Chem Eur J 9:215
Zahn S et al (2011) Pnicogen bonds: a new molecular linker? Chem Eur J 17:6034
Del Bene JE et al (2011) Structures, energies, bonding, and nmr properties of pnicogen complexes H2XP:NXH2 (X=H, CH3, NH2, OH, F, Cl). J Phys Chem A 115:13724
Sarkar S et al (2015) Experimental validation of ‘pnicogen bonding’ in nitrogen by charge density analysis. Phys Chem Chem Phys 17:2330
Tripathi G et al (2016) N···N pnicogen bonds in Boc-DOPA-OMe. Chem Phys Lett 653:117
Scheiner S (2011) Can two trivalent N atoms engage in a direct N···N noncovalent interaction? Chem Phys Lett 514:32
Avtomonov EV et al (1996) Syntheses and structures of cyclopentadienyl arsenic compounds part 1: pentamethylcyclopentadienyl arsenic dihalides (Cp*AsX2;X = F, Cl, Br, I). J Organomet Chem 524:253
Murray JS et al (2007) A predicted new type of directional noncovalent interaction. Int J Quantum Chem 107:2286
Scheiner S (2013) Detailed comparison of the pnicogen bond with chalcogen, halogen, and hydrogen bonds. Int J Quantum Chem 113:1609
Scheiner S (2011) A new noncovalent force: comparison of P···N interaction with hydrogen and halogen bonds. J Chem Phys 134:094315
Scheiner S (2011) Effects of Substituents upon the P···N noncovalent interaction: the limits of its strength. J Phys Chem A 115:11202
Bene JED et al (2012) Structures, binding energies, and spin−spin coupling constants of geometric isomers of pnicogen homodimers (PHFX)2, X = F, Cl, CN, CH3, NC. J Phys Chem A 116:3056
Moilanen J et al (2009) Weak interactions between trivalent pnictogen centers: computational analysis of bonding in dimers X3E EX3 (E = pnictogen, X = halogen). Inorg Chem 48:6740
Wiberg KB (1968) Application of the pople-santry-segal CNDO method to the cyclopropylcarbinyl and cyclobutyl cation and to bicyclobutane. Tetrahedron 24:1083
Setiawan D (2015) Strength of the pnicogen bond in complexes involving group Va elements N, P, and As. J Phys Chem A 119:1642
Bene JED et al (2014) Pnicogen-bonded anionic complexes. J Phys Chem A 118:3386
Schmauck J, Breugst M (2017) The potential of pnicogen bonding for catalysis—a computational study. Org Biomol Chem 15:8037
Bauza A et al (2013) Tetrel-bonding interaction: rediscovered supramolecular force? Angew Chem Int Ed 52:12317
Alkorta I et al (2001) Molecular complexes between silicon derivatives and electron-rich groups. J Phys Chem A 105:743
Alkorta I (2001) Aminopropylsilanes versus silatranes: an experimental and theoretical study. J Organomet Chem 625:148
Frontera A et al (2019) Tetrel bonding interactions at work: impact on tin and lead coordination compounds Coord. Chem Rev 384:107
Marin-Luna M et al (2016) Cooperativity in tetrel bonds. J Phys Chem A 120:648
Scheiner S (2017) Systematic elucidation of factors that influence the strength of tetrel bonds. J Phys Chem A 121:5561
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
Gnanasekar SP, Arunan E (2019) Inter/intramolecular bonds in TH5+ (T = C/Si/Ge): H2 as tetrel bond acceptor and the uniqueness of carbon bonds. J Phys Chem A 123:1168
Mani D, Arunan E (2014) The X−C···π (X = F, Cl, Br, CN) carbon bond. J Phys Chem A 118:10081
Southern SA, Bryce DL (2015) NMR investigations of noncovalent carbon tetrel bonds. Computational assessment and initial experimental observation. J Phys Chem A 119:11891
Mundlapati VR et al (2018) Noncovalent carbon-bonding interactions in proteins. Angew Chem Int Ed 57:16496
Bauza A, Frontera A (2016) RCH3···O interactions in biological systems: are they trifurcated H-bonds or noncovalent carbon bonds? Crystals 6:26
Taylor PG et al (2012) Further studies of fluoride ion entrapment in octasilsesquioxane cages; X-ray crystal structure studies and factors that affect their formation. Dalton Trans 41:2048
Mahmoudi G et al (2017) Anion-driven tetrel bond-induced engineering of lead(II) architectures with N′-(1-(2-pyridyl)ethylidene)nicotinohydrazide: experimental and theoretical findings. Inorg Chem Front 4:171
Thomas SP et al (2014) Experimental evidence for ‘carbon bonding’ in the solid state from charge density analysis. Chem Commun 50:49
Kost D et al (2007) Silicon rehybridization and molecular rearrangements in hypercoordinate silicon dichelates. Pure Appl. Chem. 79:1125
Bauza A et al (2015) The bright future of unconventional σ/π–hole interactions. Chem Phys Chem 16:2496
Pang X et al (2013) Co-crystallization turned on the phosphorescence of phenanthrene by C–Br···π halogen bonding, π–hole π bonding and other assisting interactions. CrystEngComm 15:2722
Wang H et al (2015) Strength order and nature of the π–hole bond of cyanuric chloride and 1,3,5-triazine with halide. Phys Chem Chem Phys 17:20636
Eskandari K, Zariny H (2010) Halogen bonding: a lump–hole interaction. Chem Phys Lett 492:9
Gamez P et al (2007) Anion binding involving π-acidic heteroaromatic rings. Acc Chem Res 40:435
Seth SK et al (2018) Quantitative analysis of weak non-covalent σ–hole and & π–hole interactions. In: Chopra D (ed) Understanding intermolecular interactions in the solid state: approaches and techniques, vol 285. Royal Society of Chemistry, London
Murray JS et al (2012) σ–holes, π–holes and electrostatically-driven interactions. J. Mol. Model. 18:541
Esrafili MD, Nurazar R (2016) Chalcogen bonds formed through π–holes: SO3 complexes with nitrogen and phosphorus bases. Mol Phys 114:276
Wang Y et al (2016) The mutual influence between π–hole pnicogen bonds and σ–hole halogen bonds in complexes of PO2Cl and XCN/C6H6 (X = F, Cl, Br). Struc. Chem. 27:1427
Wei Y et al (2018) The π-tetrel bond and its influence on hydrogen bonding and proton transfer. Chem Phys Chem 19:736
Cheng N et al (2014) The structures and properties of halogen bonds involving polyvalent halogen in complexes of FXOn (X = Cl, Br; n = 0–3)–CH3CN. New J Chem 38:1256
Azofra LM et al (2014) Noncovalent interactions in dimers and trimers of SO3 and CO. Theor Chem Acc 133:1586
Azofra LM et al (2014) Strongly bound noncovalent (SO3)n:H2CO complexes (n = 1, 2). Phys Chem Chem Phys 16:18974
Bauza A et al (2016) π–hole interactions involving nitro compounds: directionality of nitrate esters. Cryst Growth Des 16:5520
Andleeb H et al (2017) Synthesis and supramolecular self-assembly of thioxothiazolidinone derivatives driven by H-bonding and diverse π–hole interactions: a combined experimental and theoretical analysis. J Mol Struct 1139:209
Zuho H et al (2014) Non-additivity between substitution and cooperative effects in enhancing hydrogen bonds. J Chem Phys 141:244305
Rahim A et al (2017) Reciprocal carbonyl–carbonyl interactions in small molecules and proteins. Nat Commun 8:78
Burgi HB et al (1974) Stereochemistry of reaction paths at carbonyl center. Tetrahedron 30:1563
Shen S et al (2018) Insight into the π–hole···π-electrons tetrel bonds between F2ZO (Z = C, Si, Ge) and unsaturated hydrocarbons. Int J Quantum Chem 118:25521
Acknowledgements
SP and DC thank IISER Bhopal for research facilities and infrastructure. The authors thank Rohit Bhowal and Koushik Mandal for their help in editing the manuscript
Author information
Authors and Affiliations
Corresponding author
Additional information
Publisher's Note
Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.
This article is dedicated to the memory of Prof Philip Coppens, for his outstanding contributions in the area of charge density analysis and photocrystallography.
Rights and permissions
About this article
Cite this article
Pramanik, S., Chopra, D. Unravelling the Importance of H bonds, σ–hole and π–hole-Directed Intermolecular Interactions in Nature. J Indian Inst Sci 100, 43–59 (2020). https://doi.org/10.1007/s41745-019-00144-6
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s41745-019-00144-6