New Landscape of Electron-Pair Bonding: Covalent, Ionic, and Charge-Shift Bonds

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• 关键词：AIM ; Bonding ; Charge ; shift bonding ; Covalent bonding ; Electron pairing ; Electronegativity ; ELF ; Ionic bonding ; Lewis structures ; Resonance energy ; Valence bond
• 刊名：Structure & Bonding
• 出版年：2016
• 出版时间：2016
• 年：2016
• 卷：170
• 期：1
• 页码：169-211
• 全文大小：1,040 KB
• 参考文献：1.Shaik S (2007) J Comput Chem 28:51CrossRef
  2.Shaik S, Hiberty PC (2008) A chemist’s guide to valence bond theory. Wiley, Hoboken, pp 1–25
  3.Sini G, Maitre P, Hiberty PC, Shaik SS (1991) J Mol Struct (THEOCHEM) 229:163CrossRef
  4.Shaik S, Maitre P, Sini G, Hiberty PC (1992) J Am Chem Soc 114:7861CrossRef
  5.Lauvergnat DL, Hiberty PC, Danovich D, Shaik S (1996) J Phys Chem 100:5715CrossRef
  6.Shurki A, Hiberty PC, Shaik S (1999) J Am Chem Soc 121:822CrossRef
  7.Galbraith JM, Blank E, Shaik S, Hiberty PC (2000) Chem Eur J 6:2425CrossRef
  8.Lauvergnat D, Hiberty PC (1995) J Mol Struct (THEOCHEM) 338:283CrossRef
  9.Shaik S, Danovich D, Silvi B, Lauvergnat D, Hiberty PC (2005) Chem Eur J 11:6358CrossRef
  10.Zhang L, Ying F, Wu W, Hiberty PC, Shaik S (2009) Chem Eur J 15:2979CrossRef
  11.Wu W, Gu J, Song J, Shaik S, Hiberty PC (2009) Angew Chem Int Ed 48:1407CrossRef
  12.Shaik S, Danovich D, Wu W, Hiberty PC (2009) Nat Chem 1:443CrossRef
  13.Shaik S, Chen Z, Wu W, Stanger A, Danovich D, Hiberty PC (2009) ChemPhysChem 10:2658CrossRef
  14.Zhang H, Danovich D, Wu W, Braida B, Hiberty PC, Shaik S (2014) J Chem Theory Comput 10:2410CrossRef
  15.Anderson P, Petit A, Ho J, Mitoraj MP, Coote ML, Danovich D, Shaik S, Braïda B, Ess DH (2014) J Org Chem 79:9998CrossRef
  16.Silvi B, Savin A (1994) Nature 371:683CrossRef
  17.Bader RFW (1990) Atoms in molecules: a quantum theory. Oxford University Press, Oxford
  18.Shaik S, Hiberty PC (2008) A chemist’s guide to valence bond theory. Wiley, Hoboken, ch. 3, 9, 10
  19.Wu W, Su P, Shaik S, Hiberty PC (2011) Chem Rev 111:7557CrossRef
  20.Lewis GN (1916) J Am Chem Soc 38:762CrossRef
  21.Langmuir I (1919) J Am Chem Soc 41:868CrossRef
  22.Jensen WB (1984) J Chem Educ 61:191CrossRef
  23.Heitler W, London F (1927) Z Phys 44: 455–472, English Translation Hettema H (2000) Quantum chemistry classic scientific paper. World Scientific, Singapore, pp 140–155
  24.London F (1928) Z Phys 46:455CrossRef
  25.Pauling L (1939) The nature of the chemical bond. Cornell University Press, Ithaca (3rd Edition, 1960)
  26.Slater JC (1965) J Chem Phys 43:S11CrossRef
  27.van Vleck JH, Sherman A (1935) Rev Mod Phys 7:167CrossRef
  28.Calvin M (1984) J Chem Educ 61:14CrossRef
  29.Saltzman MD (1996) Bull Hist Chem 19:25
  30.Gavroglu K, Simoes A (1994) Stud Biol Phys Sci 25:47CrossRef
  31.Sanderson RT (1983) Polar covalence. Academic, New York
  32.Edmiston C, Ruedenberg K (1963) Rev Mod Phys 35:457CrossRef
  33.Rutledge RM, Saturno AF (1965) J Chem Phys 43:597CrossRef
  34.Boys SF (1960) Rev Mod Phys 32:296CrossRef
  35.Foster JM, Boys SF (1960) Rev Mod Phys 32:300CrossRef
  36.Weinhold F, Landis CR (2005) Valency and bonding: a natural bond orbital donor-acceptor perspective. Cambridge Univeristy Press, CambridgeCrossRef
  37.Weinhold F, Landis CR (2012) Discovering chemistry with natural bond orbitals. Wiley, HobokenCrossRef
  38.Bader RFW, Nguyen-Dang TT (1981) Adv Quantum Chem 14:63CrossRef
  39.Henn J, Ilge D, Leusser D, Stalke D, Engles D (2004) J Phys Chem A 108:9442CrossRef
  40.Apeloig Y (1989) In: Apeloig Y, Rappoport Z (eds) The chemistry of organic silicon compounds, vol 1. Wiley, Chichester, ch. 2
  41.Laube T (1995) Acc Chem Res 28:399CrossRef
  42.Prakash GKS, Keyaniyan S, Aniszfeld SKR, Heiliger L, Olah GA, Stevens RC, Choi H-K, Bau R (1987) J Am Chem Soc 109:5123CrossRef
  43.Kato T, Reed A (2004) Angew Chem Int Ed 43:2908CrossRef
  44.Apeloig Y, Stanger A (1987) J Am Chem Soc 109:272CrossRef
  45.Lambert JB, Kania L, Zhang S (1995) Chem Rev 95:1191CrossRef
  46.Gomes de Mesquita AH, MacGillavry CH, Eriks K (1965) Acta Crystallogr 18:437CrossRef
  47.Lambert JB, Zhao Y (1997) Angew Chem Int Ed Engl 36:400CrossRef
  48.Kim K-C, Reed CA, Elliott DW, Mueller LJ, Tham F, Lin L, Lambert JB (2002) Science 297:825CrossRef
  49.Cremer D, Kraka E (1984) Angew Chem Int Ed Engl 23:627CrossRef
  50.Low AA, Hall MB (1990) In: Maksic ZB (ed) Theoretical models of chemical bonding. Springer, New York, pp 544–591, part 2
  51.Schwarz WHE, Valtazanos P, Ruedenberg K (1985) Theor Chim Acta 68:471CrossRef
  52.Lusar R, Beltrán A, Andrés J, Noury S, Silvi B (1999) J Comput Chem 20:1517CrossRef
  53.Silvi B (2003) J Phys Chem A 107:3081CrossRef
  54.Rincon L, Almeida R (1998) J Phys Chem A 102:9244CrossRef
  55.Kraka E, Cremer D (1990) In: Maksic ZB (ed) Theoretical models of chemical bonding. Springer, New York, pp 457–543, part 2
  56.Coppens P (2005) Angew Chem Int Ed 44:6810CrossRef
  57.Coppens P (1997) X-ray densities and chemical bonding. Oxford University Press, New York
  58.Messershmidt M, Scheins S, Grubert L, Patzel M, Szeimies G, Paulmann C, Luger P (2005) Angew Chem Int Ed 44:3925CrossRef
  59.Polo V, Andres J, Silvi B (2007) J Comput Chem 28:857CrossRef
  60.Maynau D, Malrieu J-P (1998) J Chem Phys 88:3163CrossRef
  61.Hiberty PC, Ramozzi R, Song L, Wu W, Shaik S (2006) Faraday Discuss 135:261CrossRef
  62.Kutzelnigg W (1990) In: Maksic ZB (ed) Theoretical models of chemical bonding. Springer, New York, pp 1–44, part 2
  63.Ruedenberg K (1962) Rev Mod Phys 34:326CrossRef
  64.Feinberg MJ, Ruedenberg K (1971) J Chem Phys 54:1495CrossRef
  65.Wilson CQ, Goddard WA III (1972) Theor Chim Acta 26:195CrossRef
  66.Rozendaal A, Baerends EJ (1985) Chem Phys 95:57CrossRef
  67.Ruedenberg K, Schmidt M (2007) J Comput Chem 28:391CrossRef
  68.Bickelhaupt FM, Baerends EJ (2000) Rev Comput Chem 15:1CrossRef
  69.Shaik SS (1989) In: Bertran J, Csizmadia GI (eds) New theoretical concepts for understanding organic reactions, vol C267, NATO ASI series. Kluwer, Dordrecht, pp 165–217CrossRef
  70.Ploshnik E, Danovich D, Hiberty PC, Shaik S (2001) J Chem Theory Comput 7:955CrossRef
  71.Su P, Song L, Wu W, Shaik S, Hiberty PC (2008) J Phys Chem A 112:2988CrossRef
  72.Hiberty PC, Danovich D, Shurki A, Shaik S (1995) J Am Chem Soc 117:7760CrossRef
  73.Messerschmidt M, Wagner A, Wong MW, Luger P (2002) J Am Chem Soc 124:732CrossRef
  74.Platts JA, Overgaard J, Jones C, Iversen BB, Stasch A (2011) J Phys Chem A 115:194CrossRef
  75.Dunitz JD, Seiler P (1983) J Am Chem Soc 105:7056CrossRef
  76.Dunitz JD, Schweizer WB, Seiler P (1983) Helv Chim Acta 66:123CrossRef
  77.Coppens P, Yang YW, Blessing RH, Cooper WF, Larsen FK (1977) J Am Chem Soc 99:760CrossRef
  78.Savariault J-M, Lehmann MS (1980) J Am Chem Soc 102:1298CrossRef
  79.Ruedenberg K, Schwarz WHE (1990) J Chem Phys 92:4956CrossRef
  80.Schwarz WHE, Ruedenberg K, Mensching L (1989) J Am Chem Soc 111:6926CrossRef
  81.Hiberty PC, Megret C, Song L, Wu W, Shaik S (2006) J Am Chem Soc 128:2836CrossRef
  82.O’Neal SV, Schaefer HF III, Bender CF (1974) Proc Natl Acad Sci U S A 71:104CrossRef
  83.Dunning TH Jr (1984) J Phys Chem 88:2469CrossRef
  84.Bender CF, Garrison BJ, Schaefer HF III (1975) J Chem Phys 62:1188CrossRef
  85.Voter AF, Goddard WA III (1981) J Chem Phys 75:3638CrossRef
  86.Dobbs KD, Dixon CA (1993) J Phys Chem 97:2085CrossRef
  87.Bartoszek FE, Manos DM, Polanyi JC (1978) J Chem Phys 69:933CrossRef
  88.Shaik S, Hiberty PC (2004) Rev Comput Chem 20:1
  89.Hach RJ, Rundle RE (1951) J Am Chem Soc 73:4321CrossRef
  90.Pimentel GC (1951) J Chem Phys 19:446CrossRef
  91.Coulson CA (1964) J Chem Soc 1442
  92.Braida B, Hiberty PC (2013) Nat Chem 5:417CrossRef
  93.Shaik SS (1991) In: Maksic ZB, Maksic ME (eds) An encomium to Linus Pauling. Molecules in natural science and medicine. Ellis Horwood, London
  94.Braida B, Ribeyre T, Hiberty PC (2014) Chem Eur J 20:9643CrossRef
  95.Woon DE, Dunning TH Jr (2010) J Phys Chem A 114:8845CrossRef
  96.Woon DE, Dunning TH Jr (2009) J Phys Chem A 113:7915CrossRef
  97.Chen L, Woon DE, Dunning TH Jr (2009) J Phys Chem A 113:12645CrossRef
  98.Pepkin VI, Lebedev YA, Apin AY (1969) Zh Fiz Khim 43:869
  99.Bartlett N, Sladky FO (1973) In: Blair JC, Emeleus HJ (eds) Comprehensive inorganic chemistry, vol 1. Pergamon, Oxford, Chapter 6
  100.Kost D, Kalikhman I (2009) Acc Chem Res 42:303CrossRef
  101.Hajdasz DJ, Squires RR (1986) J Am Chem Soc 108:3139CrossRef
  102.Sini G, Ohanessian G, Hiberty PC, Shaik SS (1990) J Am Chem Soc 112:1407CrossRef
  103.Shaik S, Shurki A (1999) Angew Chem Int Ed 38:586CrossRef
  104.Fiorillo AA, Galbraith JM (2004) J Phys Chem A 108:5126CrossRef
  105.Coote ML, Pross A, Radom L (2003) Org Lett 5:4689CrossRef
  106.Galbraith JM, Shurki A, Shaik S (2000) J Phys Chem 104:1262CrossRef
  107.Hiberty PC, Humbel S, Danovich D, Shaik S (1995) J Am Chem Soc 117:9003CrossRef
  108.Hiberty PC, Humbel S, Archirel P (1994) J Phys Chem 98:11697CrossRef
  109.Wu W, Shaik S (1999) Chem Phys Lett 301:37CrossRef
  110.Dávalos JZ, Herrero R, Abboud J-LM, Mó O, Yáñez M (2007) Angew Chem Int Ed 46:381CrossRef
  111.Panisch R, Bolte M, Müller T (2006) J Am Chem Soc 128:9676CrossRef
  112.Lühmann N, Panisch R, Hirao H, Shaik S, Müller T (2011) Organometallics 30:4087CrossRef
  113.Llusar R, Beltran A, Andrés J, Fuster F, Silvi B (2001) J Phys Chem A 105:9460CrossRef
  114.Cho KB, Carvajal MA, Shaik S (2009) J Phys Chem B 113:336CrossRef
  115.Grochala W, Hoffmann R, Feng J, Ashcroft NW (2007) Angew Chem Int Ed 46:3620CrossRef
  116.Dognon J-P, Clavaguéra C, Pyykkö P (2009) J Am Chem Soc 131:238CrossRef
  117.Rupar P, Straoverov VN, Baines KM (2008) Science 322:1360CrossRef
  
• 作者单位：Sason Shaik (3)
  David Danovich (3)
  Benoit Braida (4) (5)
  Wei Wu (6)
  Philippe C. Hiberty (7)
  
  3. Institute of Chemistry and the Lise-Meitner Minerva Center for Computational Quantum Chemistry, The Hebrew University, Jerusalem, 9190401, Israel
  4. Sorbonne Universités, UPMC Univ. Paris 06, UMR 7616, LCT, 75005, Paris, France
  5. CNRS, UMR 7616, LCT, 75005, Paris, France
  6. The State Key Laboratory of Physical Chemistry of Solid Surfaces, Fujian Provincial Key Laboratory of Theoretical and Computational Chemistry, and College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, Fujian, 361005, China
  7. Laboratoire de Chimie Physique, UMR CNRS 8000, Groupe de Chimie Théorique, Université de Paris-Sud, 91405, Orsay Cédex, France
  
• 丛书名：The Chemical Bond II
• ISBN：978-3-319-33522-3
• 刊物类别：Chemistry and Materials Science
• 刊物主题：Chemistry
  Inorganic Chemistry
  
• 出版者：Springer Berlin / Heidelberg
• ISSN：1616-8550
• 卷排序：170

文摘

We discuss here the modern valence bond (VB) description of the electron-pair bond vis-à-vis the Lewis–Pauling model and show that along the two classical families of covalent and ionic bonds, there exists a family of charge-shift bonds (CSBs) in which the “resonance fluctuation” of the electron-pair density plays a dominant role. A bridge is created between the VB description of bonding and three other approaches to the problem: the electron localization function (ELF), atoms-in-molecules (AIM), and molecular orbital (MO)-based theories. In VB theory, CSB manifests by repulsive or weakly bonded covalent state and large covalent–ionic resonance energy, RE _CS. In ELF, it shows up by a depleted basin population with fluctuations and in AIM by a positive Laplacian. CSB is derivable also from MO-based theory. As such, CSB is shown to be a fundamental mechanism that satisfies the equilibrium condition of bonding, namely, the virial ratio of the kinetic and potential energy contributions to the bond energy. The chapter defines the atomic propensity for CSB and outlines its territory: Atoms (fragments) that are prone to CSB are compact electronegative and/or lone-pair-rich species. As such, the territory of CSB transcends considerations of static charge distribution, and it involves (a) homopolar bonds of heteroatoms with zero static ionicity, (b) heteropolar σ- and π-bonds of the electronegative and/or electron-pair-rich elements among themselves and to other atoms (e.g., the higher metalloids, Si, Ge, Sn, etc.), and (c) electron-rich hypercoordinate molecules. Several experimental manifestations of charge-shift bonding are discussed.