A theoretical evidence for mutual influence between S·· ·N(C) and hydrogen/lithium/halogen bonds: Competition and interplay between π-hole and σ-hole interactions

Structural Chemistry

Volumn 25, Issue 4, 2014, Pages 1197-1205

  Esrafili, Mehdi D ^a   Mohammadian Sabet, Fariba ^a   Solimannejad, Mohammad ^b  

^a UNIVERSITY OF MARAGHEH   (Iran)

^b ARAK UNIVERSITY   (Iran)

Author keywords

Ab initio; Chalcogen bond; Cooperativity; Electrostatic potential; Energy decomposition

Indexed keywords

EID: 84905580700     PISSN: 10400400     EISSN: None     Source Type: Journal    
DOI: 10.1007/s11224-014-0392-8     Document Type: Article

References (53)

1. Scheiner S (1997) Hydrogen bonding: a theoretical prospective. Oxford University Press, Oxford
2. Chudzinski MG, McClary CA, Taylor MS (2011) Anion receptors composed of hydrogen- and halogen-bond donor groups: modulating selectivity with combinations of distinct noncovalent interactions. J Am Chem Soc 133:10559-10567
3. Metrangolo P, Resnati G, Pilati T, Biella S (2008) In: Metrangolo P, Resnati G (eds) Halogen bonding fundamentals and applications. Springer, Berlin
4. Auffinger P, Hays FA, Westhof E, Shing PS (2004) Halogen bonds in biological molecules. Proc Natl Acad Sci USA 101:16789-16794
5. Parker AJ, Stewart J, Donald KJ, Parish CA (2012) Halogen bonding in DNA base pairs. J Am Chem Soc 134:5165-5172
6. Riley KE, Murray JS, Fanfrlík J, Řezáč J, Solá RJ, Concha MC, Ramos FM, Politzer P (2013) Halogen bond tunability II: the varying roles of electrostatic and dispersion contributions to attraction in halogen bonds. J Mol Model 19:4651-4659
7. 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
8. 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
9. Politzer P, Lane P, Concha MC, Ma YG, Murray JS (2007) An overview of halogen bonding. J Mol Model 13:305-311
10. Politzer P, Murray JS, Concha MC (2008) σ-Hole bonding between like atoms; a fallacy of atomic charges. J Mol Model 14:659-665
11. Politzer P, Murray JS, Clark T (2013) Halogen bonding and other σ-hole interactions: a perspective. Phys Chem Chem Phys 15:11178-11189
12. Politzer P, Murray JS (2013) Halogen bonding: an interim discussion. Chem Phys Chem 14:278-294
13. Shields ZP, Murray JS, Politzer P (2010) Directional tendencies of halogen and hydrogen bonds. Int J Quantum Chem 110:2823-2832
14. 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
15. 2. Theor Chem Acc 131:1114
16. 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
17. 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
18. Esrafili MD (2013) A theoretical investigation of the characteristics of hydrogen/halogen bonding interactions in dibromo-nitroaniline. J Mol Model 19:1417-1427
19. Clark T, Murray JS, Lane P, Politzer P (2008) Why are dimethyl sulfoxide and dimethyl sulfone such good solvents? J Mol Model 14:689-697
20. Bleiholder C, Werz DB, Köppel, Gleiter R (2006) Theoretical investigations on chalcogen - chalcogen interactions: what makes these nonbonded interactions bonding? J Am Chem Soc 128:2666-2674
21. Li QZ, Li R, Guo P, Li H, Li WZ, Cheng JB (2012) Competition of chalcogen bond, halogen bond, and hydrogen bond in SCSAHOX and SeCSe-HOX (X=Cl and Br) complexes. Comput Theor Chem 980(2012):56-61
22. Scheiner S (2013) Detailed comparison of the pnicogen bond with chalcogen, halogen, and hydrogen bonds. Int J Quantum Chem 113:1609-1620
23. Iwaoka M, Takemoto S, Tomoda S (2002) Statistical and theoretical investigations on the directionality of nonbonded S···O interactions. Implications for molecular design and protein engineering. J Am Chem Soc 124:10613-10620
24. Politzer P, Murray JS (2009) In: Leszczynski J, Shukla M (eds) Practical aspects of computational chemistry. Springer, Heidelberg, pp 149-163
25. Politzer P, Murray JS, Clark T (2010) Halogen bonding: an electrostatically-driven highly directional noncovalent interaction. Phys Chem Chem Phys 12:7748-7757
26. Scheiner S, Sapse EAM, Schleyer PR (1995) Recent studies in lithium chemistry: a theoretical and experimental overview. Wiley, New York
27. Ammal SSC, Venuvanalingam P (1998) π-Systems as lithium/hydrogen bond acceptors: some theoretical observations. J Chem Phys 109:9820-9830
28. Feng Y, Liu L, Wang J, Li X, Guo Q (2004) Blue-shifted lithium bonds. Chem Commun 1:88-89
29. Li Y, Wu D (2006) Do single-electron lithium bonds exist? Prediction and characterization of the H3C···Li-Y (Y=H, F, OH, CN, NC, and CCH) complexes. J Chem Phys 125:084317
30. Ault BS, Pimentel GC (1975) Matrix isolation infrared studies of lithium bonding. J Phys Chem 79:621-626
31. Li QZ, Wang YF, Li WZ, Cheng JB, Gong BA, Sun JZ (2009) Prediction and characterization of the HMgH-LiX (X=H, OH, F, CCH, CN, and NC) complexes: a lithium-hydride lithium bond. Phys Chem Chem Phys 11:2402-2407
32. - and (X···H···X)-(X=F, Cl and Br) complexes: topological analysis of electron localization function. Int J Quantum Chem 90:1108-1120
33. Ammal SSC, Venuvanalingam P (2000) Origin and nature of lithium and hydrogen bonds to oxygen, sulfur, and selenium. J Phys Chem A 104:10859-10867
34. Esrafili MD, Esmailpour P, Mohammadian F, Solimannejad M (2013) Theoretical study of the interplay between halogen bond and lithium-π interactions: cooperative and diminutive effects. Chem Phys Lett 588:47-50
35. Alkorta I, Blanco F, Deya PM, Elguero J, Estarellas C, Frontera A, Quinonero D (2010) Cooperativity in multiple unusual weak bonds. Theor Chem Acc 126:1-14
36. Ziółkowski M, Grabowski SJ, Leszczynski J (2006) Cooperativity in hydrogen-bonded interactions: ab initio and "atoms in molecules" analyses. J Phys Chem A 110:6514-6521
37. Esrafili MD, Behzadi H, Hadipour NL (2008) Theoretical study of N-H···O hydrogen bonding properties and cooperativity effects in linear acetamide clusters. Theor Chem Acc 121:135-146
38. n complexes. Chem Phys Lett 427:51-55
39. Alkorta I, Blanco F, Elguero J (2009) A computational study of the cooperativity in clusters of interhalogen derivatives. Struct Chem 20:63-71
40. Solimannejad M, Ghafari S, Esrafili MD (2013) Theoretical insight into cooperativity in lithium-bonded complexes: linear clusters of LiCN and LiNC. Chem Phys Lett 577:6-10
41. Grabowski SJ (2013) Cooperativity of hydrogen and halogen bond interactions. Theor Chem Acc 132:1347
42. Li QZ, Sun L, Liu XF, Li WZ, Cheng J, Zeng YL (2012) Enhancement of iodine-hydride interaction by substitution and cooperative effects in NCX-NCI-HMY complexes. Chem Phys Chem 13:3997-4002
43. Li Q, Hu T, An X, Li W, Cheng J, Gong B, Sun J (2009) Theoretical study of the interplay between lithium bond and hydrogen bond in complexes involved with HLi and HCN. ChemPhysChem 10:3310-3315
44. McDowell SAC, Joseph JA (2013) Cooperative effects in novel LiF/HFLiFXF (X=F, Cl, Br) clusters. J Chem Phys 138:164313
45. 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
46. 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
47. Su P, Li H (2009) Energy decomposition analysis of covalent bonds and intermolecular interactions. J Chem Phys 131:014102
48. Glendening ED, Reed AE, Carpenter JE, Weinhold F, NBO Version 3.1
49. 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
50. Bondi A (1964) van der Waals volumes and radii. J Phys Chem 68:441-451
51. Bader RFW, Carroll MT, Cheeseman JR, Chang C (1987) Properties of atoms in molecules: atomic volumes. J Am Chem Soc 109:7968-7979
52. 3N··· XY···HF complexes (X, Y=F, Cl, Br). ChemPhysChem 9:2265-2269
53. Reed AE, Curtiss LA, Weinhold F (1988) Intermolecular interactions from a natural bond orbital, donor - acceptor viewpoint. Chem Rev 88:899-926