Collect. Czech. Chem. Commun.
1987, 52, 2115-2124
https://doi.org/10.1135/cccc19872115
A study of structure of meta and para substituted phenyl and benzoyl isothiocyanates by the MNDO method
Ivan Danihela, Pavol Kristiana, Stanislav Böhmb and Josef Kuthanb
a Department of Organic Chemistry, Faculty of Natural Sciences, P. J. Šafárik University, 041 67 Košice
b Department of Organic Chemistry, Prague Institute of Chemical Technology, 166 28 Prague 6
Abstract
On the basis of the optimized MNDO calculations of a selected series of meta and para substituted phenyl and benzoyl isothiocyanates it has been found that the –NCS group is non-linear in both the cases (the deviation from linearity is about 9°). For the phenyl isothiocyanates the values of CNC angles are in the region of 146.1° - 149.0°, and for the benzoyl isothiocyanates the respective regions for the CNC and OCN angles are 146.4° - 152.1° and 117.1° - 118.5°. In the meta substituted benzoyl isothiocyanates the –CONCS group is perpendicular to the phenyl residue. The results are discussed from the point of view of the electron distribution and dipole moments of the compounds studied.
