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Charge Density and Chemical Bonding

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Book cover The Chemical Bond I

Part of the book series: Structure and Bonding ((STRUCTURE,volume 169))

Abstract

In the past 100 years, the Lewis diagram has frequently been challenged, modified, extended and rejected as being too simplistic. Those who teach chemistry to freshman, however, appreciate the diagram as one of the didactical rocks in the wild sea of ever developing science, because it is simple, easy to understand and long ranged in mediate basic chemistry. This article is aimed at the evaluation of the Lewis diagram in the light of modern charge density investigations and the topological analysis based on the quantum theory of atoms in molecules. Some old molecules like boranes, sulfate, and high-coordinate silicon will be revisited as well as some recent low-valent silicon species that were regarded impossible to make only some years ago. Can the Lewis diagram cope with new results from experiment and theory and be extended to “impossible” molecules? The answer is yes and that makes a model a good model: easy to adapt by and by and not suggesting any scientific dead ends, because the model might eventually be mistaken to be real from the inexperienced applicant.

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References

  1. Lewis GN (1916) J Am Chem Soc 38:762–785

    Article  CAS  Google Scholar 

  2. Schrödinger E (1926) Phys Rev 28:1049–1070

    Article  Google Scholar 

  3. Frenking G, Shaik S (eds) (2014) The chemical bond. Wiley-VCH, Weinheim. ISBN 978-3-527-33318-9

    Google Scholar 

  4. Abegg R (1904) Z Anorg Chem 39:330–380

    Article  CAS  Google Scholar 

  5. Werner A (1893) Z Anorg Chem 3:267–330

    Article  Google Scholar 

  6. Langmuir I (1921) Science 54(1386):59–67

    Article  CAS  Google Scholar 

  7. Johnson DR, Powell FX (1969) Science 164:950–951

    Article  CAS  Google Scholar 

  8. Carberry JJ, Retton RH (1961) J Chem Phys 35:2240–2241

    Article  Google Scholar 

  9. Shibata S, Bartell LS (1965) J Chem Phys 42:1147–1151

    Article  CAS  Google Scholar 

  10. Pauling L (1960) The nature of the chemical bond, 3rd edn. Cornell University Press, Ithaca, Chapter 5

    Google Scholar 

  11. Kutzelnigg W (1984) Angew Chem 96:262–286

    Article  CAS  Google Scholar 

  12. Kutzelnigg W (1984) Angew Chem Int Ed Engl 23:272–295

    Article  Google Scholar 

  13. Reed AE, Weinhold FJ (1986) J Am Chem Soc 108:3586–3593

    Article  CAS  Google Scholar 

  14. Reed AE, Schleyer PR (1990) J Am Chem Soc 112:1434–1445

    Article  CAS  Google Scholar 

  15. Jensen WB (2006) J Chem Educ 83:1751–1752

    Article  CAS  Google Scholar 

  16. See RF (2009) J Chem Educ 86:1241–1247

    Article  CAS  Google Scholar 

  17. Pimentel GC (1951) J Chem Phys 19:446–448

    Article  CAS  Google Scholar 

  18. Hach RJ, Rundle RE (1951) J Am Chem Soc 73:4321–4324

    Article  CAS  Google Scholar 

  19. Braïda B, Hilberty PC (2013) Nat Chem 5:417–422

    Article  Google Scholar 

  20. Molina JM, Dobado JA (2001) Theor Chem Acc 105:328–337

    Article  CAS  Google Scholar 

  21. Noury S, Silvi B, Gillespie RJ (2002) Inorg Chem 41:2164–2172

    Article  CAS  Google Scholar 

  22. Kohout M (2004) Int J Quantum Chem 97:651–658

    Article  CAS  Google Scholar 

  23. Finzel K, Grin Y, Kohout M (2012) Theor Chem Acc 131:1106–1113

    Article  Google Scholar 

  24. Durrant MC (2015) Chem Sci 6:6614–6623

    Article  CAS  Google Scholar 

  25. Koritsanszky T, Coppens P (2001) Chem Rev 101:1583–1627

    Article  CAS  Google Scholar 

  26. Gatti C, Macchi P (eds) (2011) Modern charge density analysis. Springer, Heidelberg

    Google Scholar 

  27. Stalke D (2011) Chem Eur J 17:9264–9278

    Article  CAS  Google Scholar 

  28. Stalke D (ed) (2012) Electron density and chemical bonding I (experimental, vol 146) and II (theoretical, vol 147) structure and bonding. Springer, Berlin. ISBN 0081-5993

    Google Scholar 

  29. Hansen NK, Coppens P (1978) Acta Crystallogr A 34:909–921

    Article  Google Scholar 

  30. Bader RFW (1990) Atoms in molecules – a quantum theory. Oxford University Press, New York

    Google Scholar 

  31. Pendás AM, Francisco E, Blanco MA, Gatti C (2007) Chem Eur J 13:9362–9371

    Article  Google Scholar 

  32. Bader RFW (1998) J Phys Chem A 102:7314–7323

    Article  CAS  Google Scholar 

  33. Henn J, Meindl K, Oechsner A, Schwab G, Koritsanszky T, Stalke D (2010) Angew Chem 122:2472–2476

    Article  Google Scholar 

  34. Henn J, Meindl K, Oechsner A, Schwab G, Koritsanszky T, Stalke D (2010) Angew Chem Int Ed 49:2422–2426

    Article  CAS  Google Scholar 

  35. Hey J, Leusser D, Kratzert D, Fliegl H, Dieterich JM, Mata RA, Stalke D (2013) Phys Chem Chem Phys 15:20600–20610

    Article  CAS  Google Scholar 

  36. Cremer D, Kraka E (1984) Angew Chem 96:612–614

    Article  CAS  Google Scholar 

  37. Cremer D, Kraka E (1984) Angew Chem Int Ed Engl 23:627–628

    Article  Google Scholar 

  38. Abramov Y (1997) Acta Crystallogr A 53:264–272

    Article  Google Scholar 

  39. Gatti C (2005) Z Kristallogr 220:399–457

    CAS  Google Scholar 

  40. Gatti C (2012) Struct Bond 147:193–285

    Article  CAS  Google Scholar 

  41. Engels B, Schmidt TC, Gatti C, Schirmeister T, Fink RF (2012) Struct Bond 147:47–97

    Article  CAS  Google Scholar 

  42. Sinn H, Kaminsky W (1980) Adv Organomet Chem 18:99–149

    CAS  Google Scholar 

  43. Storre J, Schnitter C, Roesky HW, Schmidt H-G, Noltemeyer M, Fleischer R, Stalke D (1997) J Am Chem Soc 119:7505–7513

    Article  CAS  Google Scholar 

  44. Stephan DW (2009) Dalton Trans 3129–3136

    Google Scholar 

  45. Stephan DW, Erker G (2010) Angew Chem Int Ed 49:46–76

    Article  CAS  Google Scholar 

  46. Stephan DW (2010) Chem Commun 46:8526–8533

    Article  CAS  Google Scholar 

  47. Flierler U, Leusser D, Ott H, Kehr G, Erker G, Grimme S, Stalke D (2009) Chem Eur J 15:4595–4601

    Article  CAS  Google Scholar 

  48. Schmøkel MS, Cenedese S, Overgaard J, Jørgensen MRV, Chen Y-S, Gatti C, Stalke D, Iversen BB (2012) Inorg Chem 51:8607–8616

    Article  Google Scholar 

  49. Rademacher P (1987) Strukturen organischer Moleküle. VCH, New York

    Book  Google Scholar 

  50. Leusser D, Walfort B, Stalke D (2002) Angew Chem 114:2183–2186

    Article  Google Scholar 

  51. Leusser D, Walfort B, Stalke D (2002) Angew Chem Int Ed Engl 41:2079–2082

    Article  CAS  Google Scholar 

  52. Leusser D, Henn J, Kocher N, Engels B, Stalke D (2004) J Am Chem Soc 126:1781–1793

    Article  CAS  Google Scholar 

  53. Henn J, Leusser D, Ilge D, Stalke D, Engels B (2004) J Phys Chem A 108:9442–9452

    Article  CAS  Google Scholar 

  54. Grabowsky S, Luger P, Buschmann J, Schneider T, Schirmeister T, Sobolev AN, Jayatilaka D (2012) Angew Chem 124:6880–6884

    Article  Google Scholar 

  55. Grabowsky S, Luger P, Buschmann J, Schneider T, Schirmeister T, Sobolev AN, Jayatilaka D (2012) Angew Chem Int Ed 51:6776–6779

    Article  CAS  Google Scholar 

  56. Kocher N, Henn J, Gostevskii B, Kost D, Kalikhman I, Engels B, Stalke D (2004) J Am Chem Soc 126:5563–5568

    Article  CAS  Google Scholar 

  57. Kost D, Kalikhman I (1998) In: Rappoport Z, Apeloig Y (eds) The chemistry of organic silicon compounds. Wiley, Chichester, pp 1339–1445

    Chapter  Google Scholar 

  58. Himmel D, Krossing I, Schnepf A (2014) Angew Chem 126:378–382

    Article  Google Scholar 

  59. Himmel D, Krossing I, Schnepf A (2014) Angew Chem Int Ed 53:370–374

    Article  CAS  Google Scholar 

  60. Frenking G (2014) Angew Chem 126:6152–6158

    Article  Google Scholar 

  61. Frenking G (2014) Angew Chem Int Ed 53:6040–6046

    Article  CAS  Google Scholar 

  62. Himmel D, Krossing I, Schnepf A (2014) Angew Chem 126:6159–6160

    Article  Google Scholar 

  63. Himmel D, Krossing I, Schnepf A (2014) Angew Chem Int Ed 53:6047–6048

    Article  CAS  Google Scholar 

  64. Gleiter R, Herberhauer G (2012) Aromaticity and other conjugated effects. Wiley-VCH, Weinheim. ISBN 978-3-527-32934-2

    Google Scholar 

  65. Matito E, Poater J, Solà M, Schleyer PR (2009) In: Chattaray PK (ed) Chemical reactivity theory. Taylor and Francis, Boca Ratón, pp 419–438

    Google Scholar 

  66. Schleyer PR (2005) Chem Rev 105:3433

    Article  CAS  Google Scholar 

  67. Tokitoh N, Wakita K, Okazaki R, Nagase S, Schleyer PR, Jiao H (1997) J Am Chem Soc 759(119):6951–6952

    Article  Google Scholar 

  68. Lee VY, Sekiguchi A (2007) Angew Chem 119:6716–6740

    Article  Google Scholar 

  69. Lee VY, Sekiguchi A (2007) Angew Chem Int Ed 46:6596–6620

    Article  CAS  Google Scholar 

  70. Sen SS, Roesky HW, Meindl K, Stern D, Henn J, Stückl AC, Stalke D (2010) Chem Commun 46:5873–5875

    Article  CAS  Google Scholar 

  71. Abersfelder K, White AJP, Rzepa HS, Scheschkewitz D (2010) Science 327:564–566

    Article  CAS  Google Scholar 

  72. Kratzert D, Leusser D, Holstein JJ, Dittrich B, Abersfelder K, Scheschkewitz D, Stalke D (2013) Angew Chem 125:4574–4578

    Article  Google Scholar 

  73. Kratzert D, Leusser D, Holstein JJ, Dittrich B, Abersfelder K, Scheschkewitz D, Stalke D (2013) Angew Chem Int Ed 52:4478–4482

    Article  CAS  Google Scholar 

  74. Schmeisser VM, Voss P (1964) Z Anorg Allg Chem 334:50–56

    Article  CAS  Google Scholar 

  75. Schenk VPW, Bloching H (1964) Z Anorg Allg Chem 334:57–65

    Article  CAS  Google Scholar 

  76. Ghadwal RS, Roesky HW, Merkel S, Henn J, Stalke D (2009) Angew Chem 121:5793–5796

    Article  Google Scholar 

  77. Ghadwal RS, Roesky HW, Merkel S, Henn J, Stalke D (2009) Angew Chem Int Ed 48:5683–5686

    Article  CAS  Google Scholar 

  78. Filippou AC, Chernov O, Schnakenburg G (2009) Angew Chem 121:5797–5800

    Article  Google Scholar 

  79. Filippou AC, Chernov O, Schnakenburg G (2009) Angew Chem Int Ed 48:5867–5870

    Google Scholar 

  80. Wang Y, Xie Y, Wei P, King RB, Schaefer HF III, Schleyer PR, Robinson GH (2008) Science 321:1069–1071

    Article  CAS  Google Scholar 

  81. Thomas Reuters (2015) Web of Science

    Google Scholar 

  82. Ott H, Pieper U, Leusser D, Flierler U, Henn J, Stalke D (2009) Angew Chem 121:3022–3026

    Article  Google Scholar 

  83. Ott H, Pieper U, Leusser D, Flierler U, Henn J, Stalke D (2009) Angew Chem Int Ed 48:2978–2982

    Article  CAS  Google Scholar 

  84. Cambridge Structural Database, Version 5.36 (2014) Cambridge Crystallographic Data Centre, Cambridge

    Google Scholar 

  85. Mondal KC, Roesky HW, Schwarzer MC, Frenking G, Neudeck S, Tkach I, Wolf H, Kratzert D, Herbst-Irmer R, Niepötter B, Stalke D (2013) Angew Chem 125:3036–3040

    Article  Google Scholar 

  86. Mondal KC, Roesky HW, Schwarzer MC, Frenking G, Neudeck S, Tkach I, Wolf H, Kratzert D, Herbst-Irmer R, Niepötter B, Stalke D (2013) Angew Chem Int Ed 52:2963–2967

    Article  CAS  Google Scholar 

  87. Mondal KC, Roesky HW, Klinke F, Schwarzer MC, Frenking G, Niepötter B, Wolf H, Herbst-Irmer R, Stalke D (2013) Angew Chem 125:1845–1850

    Article  Google Scholar 

  88. Mondal KC, Roesky HW, Klinke F, Schwarzer MC, Frenking G, Niepötter B, Wolf H, Herbst-Irmer R, Stalke D (2013) Angew Chem Int Ed 52:1801–1805

    Article  CAS  Google Scholar 

  89. Tonner R, Frenking G (2007) Angew Chem 119:8850–8853

    Article  Google Scholar 

  90. Tonner R, Frenking G (2007) Angew Chem Int Ed 46:8695–8698

    Article  CAS  Google Scholar 

  91. Dyker CA, Lavallo V, Donnadieu B, Bertrand G (2008) Angew Chem 120:3250–3253

    Article  Google Scholar 

  92. Dyker CA, Lavallo V, Donnadieu B, Bertrand G (2008) Angew Chem Int Ed 47:3206–3209

    Article  CAS  Google Scholar 

  93. Fürstner A, Alcarazo M, Gooard R, Lehmann CW (2008) Angew Chem 120:3254–3258

    Article  Google Scholar 

  94. Fürstner A, Alcarazo M, Gooard R, Lehmann CW (2008) Angew Chem Int Ed 47:3210–3214

    Article  Google Scholar 

  95. Ishida S, Iwamoto T, Kabuto C, Kira M (2003) Nature 421:725–727

    Article  CAS  Google Scholar 

  96. Niepötter B, Herbst-Irmer R, Kratzert D, Samuel PP, Mondal KC, Roesky HW, Jerabek P, Frenking G, Stalke D (2014) Angew Chem 126:2806–2811

    Article  Google Scholar 

  97. Niepötter B, Herbst-Irmer R, Kratzert D, Samuel PP, Mondal KC, Roesky HW, Jerabek P, Frenking G, Stalke D (2014) Angew Chem Int Ed 53:2766–2770

    Article  Google Scholar 

  98. Li Y, Mondal KC, Roesky HW, Zhu H, Stollberg P, Herbst-Irmer R, Stalke D, Andrada DM (2013) J Am Chem Soc 135:12422–12428

    Article  CAS  Google Scholar 

  99. Kocher N, Selinka C, Leusser D, Kost D, Kalikhman I, Stalke D (2004) Z Anorg Allg Chem 630:1777–1793

    Article  CAS  Google Scholar 

  100. Stalke D (2012) Chem Commun 48:9559–9573

    Article  CAS  Google Scholar 

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Acknowledgement

This work was supported by the Deutsche Forschungsgemeinschaft within the priority program 1178 “Experimental charge density as the key to understand chemical interactions,” the DNRF-funded Center for Materials Crystallography, the PhD program CaSuS, Catalysis for Sustainable Synthesis, funded from the Land Niedersachsen, Chemetall, Frankfurt and the Volkswagenstiftung. The author is particularly indebted to many capable students for providing the results that form the basis of this article.

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Correspondence to Dietmar Stalke .

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Stalke, D. (2016). Charge Density and Chemical Bonding. In: Mingos, D. (eds) The Chemical Bond I. Structure and Bonding, vol 169. Springer, Cham. https://doi.org/10.1007/430_2015_199

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