Experimental and Computational Study of Solid Solutions Formed between Substituted Nitrobenzoic Acids

02 May 2023, Version 1
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

We present an experimental and computational study of solid solution formation in binary systems formed by substituted nitrobenzoic acids by considering different isomers and methyl group, hydroxyl group and chlorine as the substituents. We show that the solid solution formation likelihood evaluated based on the observed solubility limit is notably affected both by the exchanged functional groups and the location of the substituents in the molecular structure. This demonstrate that the extent up to which a structure can accommodate the other molecule strongly depends on the intermolecular interactions present in the crystal structure and altered by the molecule replacement. Solid solutions form in all the tested crystal structures, and replacement ability was characterized by solubility from below 5% up to 50%. The obtained results indicated that the calculated intermolecular interaction energy change by the functional group replacement does not allow to rationalize the experimentally observed solubilities neither considering the molecules adjacent to the replace group nor all the molecules within 15 Å radius. The relative energy of the experimental structures and isostructural phases obtained from the computationally generated structure landscapes calculated at the level providing accurate energy ranking was found to be mostly consistent with the experimentally observed solubilities.

Supplementary materials

Title
Description
Actions
Title
Supporting Information
Description
Additional details and results of the crystallization experiments, results from characterization of the crystallization products of all the explored systems using PXRD patterns, DSC curves and 1H-NMR spectra, additional results and data from comparison of crystal structures, crystal structure determination, lattice parameters of solid solutions and calculation of pairwise and cumulative intermolecular interaction energy.
Actions

Supplementary weblinks

Comments

Comments are not moderated before they are posted, but they can be removed by the site moderators if they are found to be in contravention of our Commenting Policy [opens in a new tab] - please read this policy before you post. Comments should be used for scholarly discussion of the content in question. You can find more information about how to use the commenting feature here [opens in a new tab] .
This site is protected by reCAPTCHA and the Google Privacy Policy [opens in a new tab] and Terms of Service [opens in a new tab] apply.