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Paradigms and paradoxes: A personal perspective

Three-membered rings: strain versus aromaticity and carbon versus boron

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    For the premier study of the application of groups in organic chemistry and their associated heats of formation and other thermochemical properties, see the book by its pioneer, Benson, S. W.Thermochemical Kinetics; Wiley: New York, 1978, 2nd ed. For a discussion of the nature of groups and their relation with quasiatoms and their application to diverse questions in (not just organic) chemistry, see Liebman., J. F.; Van Vechten, D. InPhysical Propertiesi (Molecular Structure and Energetics); Liebman, J. F.; Greenberg, A., Eds.; VCH Publishers: New York, 1987, Vol. 2, p.315.

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    See the pioneering study, Dewar, M. J. S.Bull. Soc. Chim. Belg.,1979,88, 957.Also see Dewar, M. J. S. In Modern Models of Bonding and Delocalization; Liebman, J. F.; Greenberg, A., Eds.; VCH Publishers: New York, 1988, p. 1; and Cremer, D.; Kraka, E. In Structure and Reactivity, Liebman, J. F.; Greenberg, A., Eds.; VCH Publishers: New York, 1988, p. 65.

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    Maier, G.Angew. Chem., Int. Ed. Engl.,1988,27, 309.

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    Some of these three-membered rings have hydrogens bridging the “heavy” atoms while others have just the three “heavy” atoms. For comparisons of these two types of rings for boroncontaining species and their carbocationic analogs, see Williams, R. E.; Prakash, G. K. S.; Field, L. D.; Olah, G. A. InAdvances in Boron and the Boranes; Liebman, J. F.; Greenberg, A.; Williams, R. E., Eds.; VCH Publishers: New York, 1988, p. 191. For a discussion of experimental geometry determinations for both of these types of boron-containing compounds, see Beaudet, R. A. In the same volume p. 417 and also Mastryukov, V. S. inStereochemical Applications of Gas-Phase Electron Diffraction; Hargittai, I.; Hargittai, M. Eds.; VCH Publishers: New York, 1988, Part 1, p. 1.

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    Two useful sources for structural information on elemental boron are: Hughes, R. E.; Hoard, J. L. InThe Chemistry of Boron and Its Compounds Muetterties, E. L.Ed.; Wiley: New York, 1967, p. 25; Donohue,J. The Structure of the Elements; Wiley: New York, 1974.

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    For a discussion of these species and other neutral compounds with many borons and many triangles, see Morrison, J. A. In Liebman, J. F.; Greenberg, A.; Williams, R. E., Eds.,op. cit., p. 151.

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    For a review of the structure of the various binary metal borides, see Hughes R. E., Hoard, J. L.,op. cit.In. Our source of information on their heats of formation is Wagman, D. D.; Evans, W. H.; Parker, V. B.; Schumm, R. H.; Halow, I.; Bailey, S. M.; Churney, K. L.; Nuttall, R. L.The NBS Tables of Chemical Thermodynamic Properties: Selected Values for Inorganic and C, and C2 Organic Substances in SI Units. J. Phys. Chem. Ref. Data,1982, 11(Suppl. 2).

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    Schaefer, R.; Johnson, Q.; Smith, G. S.Inorg. Chem.,1965,4, 917.

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    There is also thermochemical data on the 1,6-“dihetero” derivative of (BH)6 −2, B2C2H6: Gal'chenko, G. L.; Tamm, N.; Brykina, E. P.; Bekker, D. B.; Petrunin, A. B.; Zhigach, A. F.russ. J. Phys. Chem.,1985,59, 1610. As with the heats of formation of the assorted binary borides, we do not know how to utilize these data to answer the question of the relative stability of octahedral versus hexagonal geometries.

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Correspondence to Joel F. Liebman or Anne Skancke.

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This study is in homage to Prof. William N. Lipscomb on the occasion of his 70th birthday.

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Liebman, J.F., Skancke, A. Paradigms and paradoxes: A personal perspective. Struct Chem 2, 201–202 (1991). https://doi.org/10.1007/BF00676632

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  • Physical Chemistry
  • Personal Perspective