Experimental and theoretical determinations of bond lengths in naphthalene, anthracene and other hydrocarbons

  title={Experimental and theoretical determinations of bond lengths in naphthalene, anthracene and other hydrocarbons},
  author={Durward William John Cruickshank and R. A. Sparks},
  journal={Proceedings of the Royal Society of London. Series A. Mathematical and Physical Sciences},
  pages={270 - 285}
  • D. Cruickshank, R. Sparks
  • Published 18 October 1960
  • Chemistry
  • Proceedings of the Royal Society of London. Series A. Mathematical and Physical Sciences
Recent independent determinations by X-ray crystallography of the C—C bond lengths in naphthalene and anthracene are shown to agree well. The experimental values agree to about 0-01 Å with both the simple molecular orbital and simple Pauling theories. These theories also make satisfactory predictions for 1.2 : 8.9-dibenzacridine and chrysene (except for the bond most affected by steric hindrance). The agreement between the two theories for aromatic molecules is traced to a correlation of their… 

Figures and Tables from this paper

Crystal and Molecular Structure of Diphenyl
X-RAY diffraction studies of crystalline diphenyl have been described by a number of authors1–4 but the bond-distances and bond-angles have not been determined as accurately as in other aromatic
Intermolecular potentials for polyacenes are represented by an atom-atom potential approximation using a revised carbon-carbon interatomic potential. The potential has an attraction term with an r-n
Conformation calculations on strained aromatic molecules
Interaction potentials for unconnected atoms are refined, together with the elastic constants needed to calculate conformations for strained molecules from the mechanical model. Equilibrium
The electronic spectra of unsaturated hydrocarbons a VESCF-CI treatment
A modified Pariser-Parr method, which allows for the inductive effect of alkyl groups by a VESCF method, has been applied to the calculation of the electronic spectra of a number of hydrocarbons. All
Anticipating π-Bond Dispositions in Cyclic, Even, Classical Hydrocarbons
A new technique, which employs π-bond placement coefficients, is presented. That technique, in conjunction with a few parameters that are readily available from traditional Huckel theory, permits one
On Perturbation Calculations for the ?-Electrons and their Application to Bond Length Reconsiderations in Aromatic Hydrocarbons
An alternative method for calculating the atom-atom, atom-bond, bond-bond and other polarizabilities in π-electron molecules, originally due to R. D. Brown, is extended to deal with orbital
Naphthalene and azulene: Theoretical comparison
Ab initio molecular orbital theory has been used to calculate the structure of naphthalene and it has been shown that the inclusion of electron correlation preferentially favors azulene over
Naphtho- and anthra-disilacyclobutadienes.
The longest-wavelength absorption bands of 3 and 4 were hypsochromically shifted compared to those of benzodisilacyclobutadiene 1a despite the extended π-electron systems.


Unit‐cell dimensions of graphite
GELLER, S. & HOARD, J. L. (1950). Acta Cryst. 3, 121. HENDE~SHOT, O. P. (1937). t~ev. Sci. Instrum. 8, 436. HE~ZBE~G, G., PATAT, F. & VE~LEGE~, H. (1937). J. Phys. Chem. 41, 123. LAUBE~GAYE~, A. W. &