28: Bonding and Non-Bonding (1992)

Sever Sternhell

Authors

Sever Sternhell Department of Organic Chemistry, University of Sydney

Abstract

Liversidge Research Lecture, delivered before the Royal Society of New South Wales, 14 October, 1992. Reproduced by permission of the Royal Society of New South Wales from J. Proc. Roy. Soc. N.S.W., 1993, 126, 1354-143.

"Over the last 10 years our group has carried out two parallel experimental investigations in physical-organic chemistry. The first one dealt with the development of a new experimental parameter for the determination of the π-bond order of the carbon-carbon double bond and the utilisation of this new parameter in the determination of the ground-state electronic structures of some unsaturated systems."

"The second investigation dealt with the limitations of a previously proposed (Bott, Field and Sternhell, 1980) semi-quantitative treatment for predicting the severity (energy penalty) of repulsive non-bonded interactions from purely structural parameters."

Author Biography

Sever Sternhell, Department of Organic Chemistry, University of Sydney

Sever Sternhell was born in Lwow, Poland, and arrived in Australia after WWII, receiving just one year of formal schooling in Australia before graduating BSc with first class honours from the University of Sydney. He worked in industry, including at the CSIRO, until 1964, with a leave of absence to undertake a PhD at Imperial College, London, before becoming a senior lecturer at the University of Sydney. In 1977 he was appointed Professor, a position he held until his retirement in 1998 as Emeritus Professor. In 1992 he was also the Chairman of the Australian Research Council.

For additional biographical information, photographic permissions, references and a list of honours, awards and publications, please see pages 2–4 of the transcript.

References

Allinger, N.L., 1976. Adv. Phys. Org. Chem., 13, 1.

Barfield, M., Collins, M.J., Gready, J.E., Sternhell, S. and Tansey, C.W., 1989. The bond-order dependence of orthobenzylic coupling constants involving a methyl group 4JMe,H . J. Am. Chem. Soc., 111, 4285-4290.

Barfield, M., Fallick, C., Hata, K., Sternhell, S. and Westerman, P., 1983. Conformational bond-order and substituent dependencies of orthobenzylic coupling. J. Am. Chem. Soc., 105, 2178-2186.

Bartle, K.D., Jones, D.W. and Matthews, R.S., 1969(a). J. Mol. Struct., 4, 445.

Bartle, K.D., Jones, D.W. and Matthews, R.S., 1969(b). Rev. Pure Appl. Chem., 19, 191.

Bott, G., Field, L.D. and Sternhell, S., 1980. Steric effects. A study of rationally designed systems. J. Am. Chem. Soc., 102, 5618-5626.

Collins, M.J., Gready, J.E., Sternhell, S. and Tansey, C.W., 1990. An NMR investigation of the Mills-Nixon effect. Aust. J. Chem., 43, 1547-1557.

Collins, M.J., Hatton, P.M., Sternhell, S. and Tansey, C.W., 1987. Substituent and ring-size dependence of the 4JMe,H coupling constant. Magn. Reson. Chem., 25, 824-828.

Collins, M.J., Hatton, P.M. and Sternhell, S., 1992. An N.M.R. investigation of ground state polarisation of some substituted aromatic systems. Aust. J. Chem., 45, 1119.

Collins,M.J., Sternhell, S. and Tansey, C.W., 1990. NMR studies of bond order in azulene, biphenylene and 1,6 methano[10]annulene. Aust. J.Chem., 43, 1541-1546.

Cosmo, R., Hambley, T.W. and Sternhell, S., 1987. Skeletal deformation in 4,5-disubstituted 9,10-dihydrophenanthrenes and 4,5-disubstituted phenanthrenes. J. Org. Chem., 52, 3119-3123.

Cosmo, R., Hambley, T.W. and Sternhell, S., 1987. Anomalous internuclear distances in 1,8-substituted naphthalenes and 4,5-substituted phenanthrenes. Tetrahedron Letters, 28, 62396240.

Cosmo, R. and Sternhell, S., 1987. Steric Effects. Inversion of 9,10-dihydro-4,5- disubstituted phenanthrenes. Aust. J. Chem., 40, 35-47.

Craw, J.S., Hush, N.S., Sternhell, S. and Tansey, C.W., 1992. The Relationship between partial bond fixation induced by through-bond and/or through-space perturbations in non-planar benzene derivatives and 1H spinspin coupling constants. J. Phys. Chem., 961, 5 7 5 3.

Crossley, M.J., Forster, A.J., Harding, M.M. and Sternhell, S., 1987. Steric Effects on atropoisomerism in tetraarylporphyrins. J. Am. Chem. Soc., 109, 341-348.

Crossley, M.J., Harding, M.M. and Sternhell, S., 1992. Use of NMR spectroscopy to determine bond orders between β- and β'-pyrrolic positions of porphyfins: structural differences between free-base and metalloporphyrins. J. Am. Chem. Soc., 114, 3266.

Gready, J.E., Hambley, T.W., Kakiuchi, K., Kobiro, K., Sternhell, S., Tansey, C.W. and Tobe, Y., 1990. NMR studies of bond order in distorted aromatic systems. J. Am. Chem. Soc., 112, 7537-7540.

Gready, J.E., Hatton, P.M. and Sternhell, S., 1992. NMR studies of bond-order in heteroaromatic systems. J. Heterocyclic Chem., 29, 935.

Hambley, T.W. and Stemhell, S., (unpublished data from these laboratories, 1992).

Hambley, T.W., Sternhell, S. and Tansey, C.W., 1990. The Synthesis and Structure of 3,4-di-tert-butylbenzoic acid. Aust. J. Chem., 43, 807-814.

Hatton, P. and Sternhell, S., 1993. An NMR Investigation of Polarisation of Pyridine by +R Substituents and a Proposed New Method for Determination of the Substituent Resonance Parameter (σR). Aust. J. Chem., 46, 149.

Joseph-Nathan, P., Garcia-Martinez, C. and Morales-Rios, M.S., 1990. Magn. Reson. Chem., 28, 311.

Kalinowski, H.O., Berger, S. and Braun, S., 1984. 13C N.M.R. Spectroscopy. John Wiley and Sons, Chichester.

Marshall, J.L., 1983. Carbon-Carbon and Carbon-Proton N.M.R. Couplings: Applications to Organic Stereochemistry and Conformational Analysis. Vol. 2, Verlag Chemie International, Deerfield Beach, Florida, U.S.A.

Newsom, I.A., 1984. PhD Thesis, University of Sydney.

Pauling, L., 1980. Acta crystallogr., B36, 1898.

Sternhell, S. and Tansey, C.W., 1990. NMR studies of bond order in sterically distorted phenanthrenes. Aust. J. Chem., 43, 11577-1580.