Abstract
Noncovalent interactions play a significant role in a wide variety of biological processes and bio-inspired species. It is, therefore, important to have at hand suitable computational methods for their investigation. In this paper, we report on the contribution of dispersion and hydrogen bonds in both stacked and T-shaped catechol dimers, with the aim of delineating the respective role of these classes of interactions in determining the most stable structure. By using second-order Møller–Plesset (MP2) calculations with a small basis set, specifically optimized for these species, we have explored a number of significant sections of the interaction potential energy surface and found the most stable structures for the dimer, in good agreement with the highly accurate, but computationally more expensive coupled cluster single and double excitation and the perturbative triples (CCSD(T))/CBS) method.
Highlights
Nowadays, there is a general consensus about the primary role played by noncovalent interactions, in particular those involving aromatic rings, in molecular, life, and materials sciences
In addition to being responsible for key biological processes that range from base stacking in deoxyribonucleic acid (DNA) [1], to the color of red wine [2] and, more generally, food quality [3], it is of the foremost importance to understand, rationalize and, exploit their features in cutting-edge applications as advanced catalysis [4,5], biomedical materials [6,7] and novel drugs design [8], advanced organic photovoltaics [9,10,11,12,13], complex self-assembled structures [14], or bio-nano-materials [15,16]
We have reported our study of the intermolecular landscape of a catechol dimer with a two‐fold interest
Summary
There is a general consensus about the primary role played by noncovalent interactions, in particular those involving aromatic rings, in molecular, life, and materials sciences. The presence of additional functional groups can introduce other kinds of interactions (like e.g., hydrogen (HB) or halogen bonds), leading to nontrivial interference effects, which tune both the structure and the properties of the resulting material In this framework, computational methods can play a crucial role for rational design and interpretation, provided that they are able to couple reliability, feasibility, and ability to unravel the different contributions [18,19]. Successively refined by Hobza and Zahradnik [52], based on the use MP2 calculations with the small 6-31G* basis set, modified by reducing to 0.25 the exponent of the d polarization function placed on each carbon atom of the benzene dimer Such an approach, often referred to as MP2/6-31G*(0.25), was fully validated with reference to interaction energies of benzene and a few other aromatic dimers computed at the CCSD(T)/CBS level [53,54,55,56,57,58,59,60,61]. In the following these results will be discussed in comparison with our findings
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