Related Experiment Video
Updated: Mar 2, 2026

Construction and Systematical Symmetric Studies of a Series of Supramolecular Clusters with Binary or Ternary Ammonium Triphenylacetates
Published on: February 15, 2016
Density functional theory study of the conformational space of phenyl benzoate, a common fragment in many mesogenic
Giorgio Cinacchi1, Giacomo Prampolini
1Dipartimento di Chimica, Università di Pisa, Via Risorgimento 35, I-56126 Pisa, Italy. g.cinacchi@sns.it
Abstract:
The complete conformational space of phenyl benzoate (three coupled rotors) has been studied by B3LYP density functional theory (DFT) at the 6-31+G* basis set level. The overall quality of the DFT results has been checked via Möller-Plesset second-order perturbation theory (MP2) calculations performed on a few significant molecular geometries. Contrary to the general belief, we have found that rotation around the C(=O)-O bond is not more restricted than rotation around the C(=O)-C bond. We have commented on the location and magnitude of the molecular dipole moment and their dependence on conformation. The energy data have been fitted through an expression containing a Fourier expansion plus a Lennard-Jones term, suitable to be used in computer simulations or to assist analysis of experimental data.
Related Concept Videos
Structure of Benzene: Molecular Orbital Model
¹H NMR of Conformationally Flexible Molecules: Temporal Resolution
Conformations of Cyclohexane
The chair form is the most stable and derives its name from its resemblance to the “easy chair.” In the chair conformation, two carbon atoms are arranged out-of-plane — one above and one below, minimizing the torsional strain. In the chair form, the bond angle is very close to the ideal...
Stability of Substituted Cyclohexanes
The two chair conformations of cyclohexanes undergo rapid interconversion at room temperature. Both forms have identical energies and stabilities, each comprising equal amounts of the equilibrium mixture. Replacing a hydrogen atom with a functional group makes the two conformations energetically non-equivalent.
For example, in...
Structure of Benzene: Kekulé Model
He proposed that benzene has a cyclic structure of six carbon atoms attached to one hydrogen atom each, with three alternating pi bonds.
¹H NMR of Conformationally Flexible Molecules: Variable-Temperature NMR

