Overcoming lability of extremely long alkane carbon-carbon bonds through dispersion forces

Nature

Volumn 477, Issue 7364, 2011, Pages 308-311

  Schreiner, Peter R ^a   Chernish, Lesya V ^b   Gunchenko, Pavel A ^b   Tikhonchuk, Evgeniya Yu ^b   Hausmann, Heike ^a   Serafin, Michael ^c   Schlecht, Sabine ^c   Dahl, Jeremy E P ^d   Carlson, Robert M K ^d   Fokin, Andrey A ^a,b  

^a JUSTUS LIEBIG UNIVERSITY   (Germany)

^b NATIONAL TECHNICAL UNIVERSITY OF UKRAINE   (Ukraine)

^c UNIVERSITY OF LEIPZIG   (Germany)

^d STANFORD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKANE; CARBON; DIAMOND; HYDROCARBON; HYDROGEN; NANOPARTICLE;

ALKANE; CARBON; CHEMICAL BONDING; ELECTRON; EMPIRICAL ANALYSIS; MOLECULAR ANALYSIS; TEMPERATURE EFFECT; THEORETICAL STUDY;

ARTICLE; CHEMICAL BOND; DECOMPOSITION; DISPERSION; HYDROGEN BOND; PARTICLE SIZE; PRIORITY JOURNAL;

EID: 80052865801     PISSN: 00280836     EISSN: 14764687     Source Type: Journal    
DOI: 10.1038/nature10367     Document Type: Article

References (38)

1. Grimme, S. Seemingly simple stereoelectronic effects in alkane isomers and the implications for Kohn-Sham density functional theory. Angew. Chem. Int. Ed. 45, 4460-4464 (2006). (Pubitemid 44105611)
2. Wodrich, M. D. et al. The concept of protobranching and its many paradigm shifting implications for energy evaluations. Chem. Eur. J. 13, 7731-7744 (2007). (Pubitemid 47477482)
3. de Silva, K. M. N. & Goodman, J. M. What is the smallest saturated acyclic alkane that cannot be made? J. Chem. Inf. Model. 45, 81-87 (2005). (Pubitemid 40736959)
4. Zavitsas, A. A. The relation between bond lengths and dissociation energies of carbon-carbon bonds. J. Phys. Chem. A 107, 897-898 (2003).
5. Kaupp, M., Metz, B. & Stoll, H. Breakdown of bond length-bond strength correlation: a case study. Angew. Chem. Int. Ed. 39, 4607-4609 (2000). (Pubitemid 32059121)
6. Gordy, W.Arelationbetweenbondforceconstants,bondorders,bondlengths,and the electronegativities of the bonded atoms. J. Chem. Phys. 14, 305-320 (1946).
7. Huggins, M. L. Atomic radii. IV. Dependence of interatomic distance on bond energy. J. Am. Chem. Soc. 75, 4126-4133 (1953).
8. Pauling, L. The Nature of the Chemical Bond (Cornell Univ. Press, 1960).
9. Schwertfeger, H., Fokin, A. A. & Schreiner, P. R. Diamonds are a chemist's best friend: diamondoid chemistry beyond adamantane. Angew. Chem. Int. Ed. 47, 1022-1036 (2008). (Pubitemid 351204395)
10. Grimme, S. Accurate description of van derWaals complexes by density functional theory including empirical corrections. J. Comput. Chem. 25, 1463-1473 (2004).
11. Tang, K.-T. & Toennies, J. P. Johannes Diderik van der Waals: a pioneer in the molecular sciences and Nobel prize winner in 1910. Angew. Chem. Int. Ed. 49, 9574-9579 (2010).
12. Gronert, S. The folly of protobranching: turning repulsive interactions into attractive ones and rewriting the strain/stabilizationenergies of organic chemistry. Chem. Eur. J. 15, 5372-5382 (2009).
13. Suzuki, T., Takeda, T., Kawai, H. & Fujiwara, K. Ultralong C-C bonds in hexaphenylethane derivatives. Pure Appl. Chem. 80, 547-553 (2008).
14. Fritz, G., Wartanessian, S., Matern, E., Höle, W. & von Schnering, H. G. Bildung siliciumorganischer Verbindungen. 85. Bildung, Reaktionen und Struktur des 1,1,3,3-tetramethyl-2,4-bis(trimethylsilyl)-1,3- disilabicyclo[1.1.0]butans. Z. Allg. Anorg. Chem. 475, 87-108 (1981).
15. McBride, J. M. The hexaphenylethane riddle. Tetrahedron 30, 2009-2022 (1974).
16. Vreven, T. & Morokuma, K. Prediction of the dissociation energy of hexaphenylethane using the ONIOM(MO: MO: MO) method. J. Phys. Chem. A 106, 6167-6170 (2002). (Pubitemid 35289896)
17. Kahr, B., van Engen, D. & Mislow, K. Length of the ethane bond in hexaphenylethane and its derivatives. J. Am. Chem. Soc. 108, 8305-8307 (1986).
18. Kammermeier, S., Jones, P. G. & Herges, R. [212] cycloaddition products of tetradehydrodianthracene: experimental and theoretical proof of extraordinary long C-C single bonds. Angew. Chem. Int. Edn Engl. 36, 1757-1760 (1997).
19. Winiker, R., Beckhaus, H. D. & Rühardt, C. Thermische Stabilitä, Spannungsenthalpie und Struktur symmetrisch hexaalkylierter Ethane. Chem. Ber. 113, 3456-3476 (1980).
20. Flamm-terMeer, M. A., Beckhaus, H. D., Peters, K., von Schnering, H. G.& Rühardt, C. Thermolabile hydrocarbons, XXVII. 2,3-di-1-adamantyl-2, 3-dimethylbutane; long bonds and low thermal stability. Chem. Ber. 118, 4665-4673 (1985).
21. Rühardt, C. & Beckhaus, H. D. Towards an understanding of the carbon-carbon bond. Angew. Chem. Int. Edn Engl. 19, 429-440 (1980).
22. Rühardt, C. & Beckhaus, H.-D. Consequences of strain for the structure of aliphatic molecules. Angew. Chem. Int. Edn Engl. 24, 529-538 (1985). (Pubitemid 15581444)
23. Boese, R., Weiss, H.-C. & Bläer, D. The melting point alternation in the short-chain n-alkanes: single-crystal X-ray analyses of propane at 30 K and of n-butane to n-nonane at 90 K. Angew. Chem. Int. Ed. 38, 988-992 (1999). (Pubitemid 29180982)
24. Grimme, S. et al.When do interacting atoms forma chemical bond? Spectroscopic measurements and theoretical analyses of dideuteriophenanthrene. Angew. Chem. Int. Ed. 48, 2592-2595 (2009).
25. Donohue, J.& Goodman, S. H. The crystal structure of adamantane: an example of a false minimum in least squares. Acta Crystallogr. 22, 352-354 (1967).
26. Zhao, Y. & Truhlar, D. G. The M06 suite of density functionals for main group thermochemistry, thermochemical kinetics, noncovalent interactions, excited states, and transition elements: two newfunctionals and systematic testing of four M06-class functionals and 12 other functionals. Theor. Chem. Acc. 120, 215-241 (2008).
27. Takatani, T.&Sherrill, C. D. Performance of spin-component- scaledMoller-Plesset theory (SCS-MP2) for potential energy curves of noncovalent interactions. Phys. Chem. Chem. Phys. 9, 6106-6114 (2007).
28. Maier, G., Pfriem, S., Schäer, U.&Matusch, R. Tetra-tert-butyltetrahedrane. Angew. Chem. Int. Edn Engl. 17, 520-521 (1978).
29. Wang, Y. Z. & Robinson, G. H. Unique homonuclear multiple bonding in main group compounds. Chem. Commun. (Camb.) 5201-5213 (2009).
30. Dyker, C. A. & Bertrand, G. Soluble allotropes of main-group elements. Science 321, 1050-1051 (2008).
31. Becke, A. D. Density-functional thermochemistry. III. The role of exact exchange. J. Chem. Phys. 98, 5648-5652 (1993).
32. Lee, C. T., Yang, W. T. & Parr, R. G. Development of the Colle-Salvetti correlationenergy formula into a functional of the electron-density. Phys. Rev. B 37, 785-789 (1988).
33. Grimme, S. Semiempirical GGA-type density functional constructed with a longrange dispersion correction. J. Comput. Chem. 27, 1787-1799 (2006). (Pubitemid 44672561)
34. Schwabe, T. & Grimme, S. Towards chemical accuracy for the thermodynamics of large molecules: new hybrid density functionals including non-local correlation effects. Phys. Chem. Chem. Phys. 8, 4398-4401 (2006).
35. Becke, A. D. Density-functional thermochemistry. V. Systematic optimization of exchange-correlation functionals. J. Chem. Phys. 107, 8554-8560 (1997). (Pubitemid 127611634)
36. Binkley, J. S., Pople, J. A. & Hehre, W. J. Split valence basis sets. J. Am. Chem. Soc. 102, 939-947 (1980).
37. Frisch, M. J, et al. Gaussian 03 v.D.02 (Gaussian, Inc., 2003).
38. Frisch, M. J, et al. Gaussian09 v.B.01 (Gaussian, Inc., 2009).