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Specific Intermolecular Interactions of Organic Compounds pp 1–28Cite as

Reverse Dative Bond in Organic Compounds, Molecular Complexes and Inconsistency of the sp 3-Hybridization Model with Respect to Carbon Atom

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Abstract

The failure was revealed of the model of the sp 3-hybridization of the carbon atom since it contradicted the reliably established relationships of the variation of thermodynamic and thermochemical properties of organic and organoelemental compounds proved on a large array of alkyls of elements of the II–VI groups of the Periodic Table. A concept was introduced of a reverse dative intramolecular bond in the molecules of these compounds implying the ability of the carbon atom to attain the pentacoordinate state forming specific intermolecular interactions via the essentially unshared 2s 2(c) electron pair. The validity of these concepts was confirmed by the quantum-chemical calculations of the electronic structures of alkyl molecules AR k which showed the existence of the bond C(e) → A(0e) formed by the valence 2s 2(c) electron pair localized prevailingly on the carbon atom and the vacant orbital localized on the A atom.

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References

  1. Skinner HA, Connor IA (1987) In: Liebman IF, Creenberg A (eds) Molecular structure and energetic. New York

    Google Scholar 

  2. Pilcher G (1982) In: Ribeiro da silva MAV (eds) Thermochemistry and its applications to chemical and biochemical systems. Dordrecht, Boston, Lancaster

    Google Scholar 

  3. Rabinovich IB, Nesterov VN, Telnov VI, Sheiman MS (1996) Thermodynamics of metalorganic compounds. University of N. Novgorod, N. Novgorod

    Google Scholar 

  4. Talrose VL, Lubimova AL (1952) Secondary process in the ion source of the mass spectrograph. Doclady A.S. SSSR, Russia, p 86, 99

    Google Scholar 

  5. Olan GA, Surya Prakash GK, Wlliams RE, Field LD, Wade K (1987) Hypercarbon chemistry. Wiley-Interscience/Wiley, New York/Toronto, ON/Singapore

    Google Scholar 

  6. Minkin VI, Miniaev PM (1985) No classical structure organic compounds. Univercity of Rostov on Done, Rostov on Done

    Google Scholar 

  7. Pullman A, Bertho H, Gissner-Prettre C, Hinton JF, Harpool D (1978) A ab initio study of a nuclear side: Iridine. J Am Chem Soc 100:3991

    Article  CAS  Google Scholar 

  8. Ohtaki H, Funaki A, Role BM, Reibnegger GJ (1983) The structural of liquid formamide studied by means of X-ray diffraction and initio LCGO-MO-SCF calculation. Bull Chem Soc Jpn 56:2115

    Google Scholar 

  9. Ohtaki H, Itoh S (1983) Structure of liquid N,N-dimethylformamide studied by means of X-ray diffraction. Z Naturforsch 40A:1315

    Google Scholar 

  10. Ohtaki H, Ishiguro SI (1994) In: Mamontov G, Popov AJ (eds) Chemistry of nonaqueous solution. Current progress. VCH, New York, pp 178–226

    Google Scholar 

  11. Krestov GA, Vinogradov VI, Kesle IyM (1986) Modern problem of solution chemistry. Nauka, Moscow

    Google Scholar 

  12. Baev AK (1969) Problems of chemical nature of phase transformation. General and applied chemistry, vol 1. Vaisheshika Educating, Minsk, pp 197–206

    Google Scholar 

  13. Baev AK (1969) Phase condition and complex formation ability of halogenide metals. General and applied chemistry, vol 1. Vaisheshika Educating, Minsk, pp 207–218

    Google Scholar 

  14. Baev AK (2001) Russ J Izvestiya Vischich Ucheb Zaved Chem Chemo Technol 44:3–13

    CAS  Google Scholar 

  15. Rid R, Prausnic Dzh, Shervud T (1977) The properties of gas and liquids. New York

    Google Scholar 

  16. Baev AK (1987) Chemistry of gas-heterogenic systems of elementorganic compounds. Science and Technology, Minsk

    Google Scholar 

  17. Belousov VP, Morachevakei AG (1970) Heat mixing of liquids. Chemistry, Leningrad

    Google Scholar 

  18. Belousov VP, Morachevakei AG, Panov MYu (1981) Heat properties of non-electrolyte solutions. Chemistry, Leningrad, p 264

    Google Scholar 

  19. Gurianova EN, Goldshtain IG, Romm IP (1973) Donor-acceptor bonds. Chemistry, Moscow

    Google Scholar 

  20. Nikiforov MYy, Alper GA, Durov DA, Korolev VP et al (1989) Nonelectrolyte solutions in liquids. Nauca, Moscow

    Google Scholar 

  21. Korolkov DV (1992) Electron structure and properties of compounds no-transition elements. Chemistry, St. Petersburg

    Google Scholar 

  22. Mathieu J, Panico E (1975) Mechanisms reactionnels a chimie organique. Hermann, Paris

    Google Scholar 

  23. Ehrenson S (1968) Theory of electron effect at formation of complex of trimethylamine with trimethylborium. Theor Chim Acta 10:193

    Article  CAS  Google Scholar 

  24. Boer FP, Newton MD (1966) Molecular orbital’s for boron hydrides parameterized from SEF-model calculations. J Am Chem Soc 88:2361–2366

    Article  CAS  Google Scholar 

  25. Gallais F, Voigt D, Laba JF (1965) Generalization comprehension “electro negativity” at calculation of effect electro negativity of atom in saturated molecule. J Chem Phys 62:761

    CAS  Google Scholar 

  26. Baev AK (1972) Complex formation ability halogenides of second – six groups periodical system. General and applied chemistry, vol 5. Vaisheshika Educating, Minsk, pp 35–51

    Google Scholar 

  27. Baev AK (1992) Structural-energetic aspects of association interactions of alkyls elements of I–VI groups. Russ J Chem Thermodyn Thermo Chem 1:143

    CAS  Google Scholar 

  28. Schustorovich EM (1978) Chemical bonds in coordination compounds. Knowledge, Moscow

    Google Scholar 

  29. Baev AK (1986) Structure and energy of metals carbonyls. Vischaia Schkola, Minsk

    Google Scholar 

  30. Korolkov DV (1977) Development of theory valence. Chemistry, Leningrad, p 194

    Google Scholar 

  31. Kato H, Yamaguche K et al (1965) Electron structure some galogenides and alkyl borium and aluminum. Bull Chem Soc Jpn 36:2144

    Article  Google Scholar 

  32. Hoffmann RK (1963) Distribution of electron levels in alkanes. Chem Phys 39:1397

    CAS  Google Scholar 

  33. Hoffmann RJ (1964) Theory of ecsictones at the notion of secondary quantization. Chem Phys 40:2474

    CAS  Google Scholar 

  34. Armstrong DR, Perkins PG (1969) Calculation σ–π and π–σ* – transfer at vinyl borium. J Chem Soc A: 1044

    Google Scholar 

  35. Moirean MC, Veillard AH (1968) Quant mechanic calculation of the barrier of inner rotation. II Molecule borazine BH3-NH3. Theor Chim Acta 11:344

    Article  Google Scholar 

  36. Levinson KA, Perkins PG (1970) Methylaluminium compounds. II. The electronic structure of the trimethylaluminium. Theory Chim Acta 17:15–17

    Article  Google Scholar 

  37. Sheldrick GM, Sheldrick WS (1970) Crystal structure of trimethylthallium. J Chem Soc Sec A Inorg Phys Theor Chem: 28–30

    Google Scholar 

  38. Baev AK (2001) Pentacoordinated carbon atom in intermolecular interaction in solutions of alkyl compounds of non-transition elements. In: Book of abstract. VIth international symposium on carbonion chemistry. Marburg, Germany, p 75

    Google Scholar 

  39. Baev AK (2001) Thermodynamics and specific intermolecular interactions in solutions of non-electrolytes with pentacoordinated carbon atom. In: Book of abstract. 27th international conference on solution chemistry. Vaals, Netherlands, p 36

    Google Scholar 

  40. Baev AK (2001) Specific interactions in solvates solutions of non-electrolytes with isostructural molecules components and pentacoordinated carbon atom. In: Book of abstract. VIIIth international conference. The problems of solution and complex formation in solution. Ivanovo, Russia, p 246

    Google Scholar 

  41. Baev AK, Korolkov DV (2003) Phenomenon of dative bond in elementorganic compounds. In: Book of abstract. XVth FECHEM conference on organometallic chemistry. University of Zurich, Switzerland, p 350

    Google Scholar 

  42. Baev AK (2003) Novel approaches to the structure of functional solvents and elementorganic compounds with saturated hydrocarbon ligands and their solvates in binary systems. In: Book of abstract. 27th international conference on solution chemistry. Debrecen, Hungary, p 79

    Google Scholar 

  43. Baev AK (2004) Insolvency of sp3-gibrydixation model of carbon atom and chemistry of non-electrolytes solutions. In: Book of abstract. IXth international conference. The problems of solution and complex formation in solution. Ivanovo, Russia, pp 62–64

    Google Scholar 

  44. Baev AK (2004) Lack of co-ordination of thermodynamic properties of elementorganic compounds with sp3-gibrydixation model of carbon atom and its insolvency. In: Book of abstract. Russian research symposium on thermochemistry and kalorimetry. Nizhny Novgorod, Russia, pp 40–41

    Google Scholar 

  45. Becke AD (1993) Density-functional thermochemistry. II. New mixing Hartri-Fock and local density-functional theory. J Chem Phys 98:5648

    Article  CAS  Google Scholar 

  46. Bartolotti LJ, Parr RG, Tal Y (1998) Thomas–Fermi theory from a perturbative treatment of the hydrogenic limit energy density functional a possible link to local density functional theory. Int J Quant Chem 34:509–515

    Article  Google Scholar 

  47. Frisch MA, Trucks GW, Schigell HR, Gill PM, Johnson BG, Robbs MA Gaussian 94, Revision G.3

    Google Scholar 

  48. Baev AK, Vitalev SE (1989) Thermodynamic vaporization and association of triethylaluminium. Vesti Akademii Navuk Belarusii 2:58–63

    Google Scholar 

  49. Vitalev SE, Baev AK (1993) Thermodynamic vaporization and association of trimethylaluminum. Russ J Izvestiya Vischich Ucheb Zaved Chem Chemo Technol 36:36–40

    CAS  Google Scholar 

  50. Coulson CA (1961) Valence. Oxford University Press, Oxford

    Google Scholar 

  51. Baev AK (1997) Thermodynamic analyses of structural changes in systems Zn(CH3)2-M(CH3)2 (Te, S, Se). Russ J Inorg Chem 42:662–672

    CAS  Google Scholar 

  52. Baev AK (1997) Insolvency sp3-hybridization and reverse dative bond of alkyl compound and molecular complexes. In: Book of abstract. International symposium “the research of Georg wilting relevance to chemistry today”. Heidelberg, Germany, p 21

    Google Scholar 

  53. Baev AK (1998) Solvation with pentocoordinate carbon and complication in solution of alkyls the third group elements. In: Book of abstract. VIIth international conference. The problems of solution and complex formation in solution. Ivanovo, Russia, p 2

    Google Scholar 

  54. Baev AK (1998) Pentacoordinated carbon in liquid state and solutions of the alkyls main group element. In: Book of abstract. XVIIth international conference on organometallic chemistry. Munich, Germany, p 18

    Google Scholar 

  55. Baev AR (1998) Thermodynamic study of structural changes in system dimethylcadmium-dimethylmercury. Russ J Inorg Chem 43:1325–1331

    CAS  Google Scholar 

  56. Baev AK, Cherniak IN (2000) Equilibrium liquid-vapor in systems trimethylaluminium-trimethylarsin and trimethylindium-trimethylphosphin. Russ J Phys Chem 74:980–985

    CAS  Google Scholar 

  57. Baev AK (2001) Thermodynamic parameters of solutions of binary system dimethylzinc-trimethylgallium. Russ J Phys Chem 75:1180–1182

    Google Scholar 

  58. Baev AR (2001) Thermodynamics of solutions trimethylaluminum and trimethylgallium. Russ J Coord Chem 27:637–640

    Article  Google Scholar 

  59. Baev AK (1993) Unknown particular interacting and hypothesis of sigma-reverse bond in II–VI groups elements alkyls. In: 1st journal of organometallic chemistry conference on applied organometallic chemistry. Munchen, Germany, p 115

    Google Scholar 

  60. Baev AK (2009) Phenomenological significance of nonidentical sp3-hybridization model and nature of interaction in chemistry of liquid non-electrolytes and chemical thermodynamics. In: Book of abstract. Xth international conference on physical and coordination chemistry of porphyrines and their analogous. Ivanovo, Russia, July 2009, p 86

    Google Scholar 

  61. Baev AК (1996) Pentacoordinated carbon atom at intermolecular interactions. Russ J Coord Chem 22:399–402

    Google Scholar 

  62. Pauling L (1970) General chemistry. W.N. Freeman and Company, San Francisco, CA

    Google Scholar 

  63. Vilkov LV, Mastrukov VS, Sadova NI (1978) Determination of geometrical structure of free molecules. Chemistry, Leningrad

    Google Scholar 

  64. Nefedov VI, Vovna VI (1989) Electron structure of organic and elementorganic compounds. Nauka, Moscow, p 175

    Google Scholar 

  65. Gallas F, Loth P, Labaire JF (1966) Study “concrete condition” σ-bond of some molecules tricoordinated phosphorus. J Chem Phys 63:413

    Google Scholar 

  66. Gallas F, Loth P, Labaire JF (1967) About some products adding type of 1:1 bromidealuminum and triethylaluminium with aliphatic sulphides and phosphines. Compt Rend C265: 363

    Google Scholar 

  67. Jolly WL, Bomben KD, Eyermann CJ (1984) Core-electron binding energies for gaseous atoms and molecules. Atom Data Nucl Data Tables 31:433–493

    Article  CAS  Google Scholar 

  68. Galkin VI, Salchov PD, Cherkasov PA (1995) New possibility for application of the model of frontal sterical. I. Theoretical calculations of the sterical factor at the theory of collisions and structure of activated complexes. Russ J Org Chem 29:1921–1926

    Google Scholar 

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  1. Dept. of Chemistry, International Sakharov Environmental Uni, Dolgobrodskaya Street 23, 220009, Minsk, Belarus

    Prof. Alexei K. Baev

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Baev, A.K. (2012). Reverse Dative Bond in Organic Compounds, Molecular Complexes and Inconsistency of the sp 3-Hybridization Model with Respect to Carbon Atom. In: Specific Intermolecular Interactions of Organic Compounds. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-21622-0_1

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